GB799361A - Acridine compounds and the preparation thereof - Google Patents

Acridine compounds and the preparation thereof

Info

Publication number
GB799361A
GB799361A GB474756A GB474756A GB799361A GB 799361 A GB799361 A GB 799361A GB 474756 A GB474756 A GB 474756A GB 474756 A GB474756 A GB 474756A GB 799361 A GB799361 A GB 799361A
Authority
GB
United Kingdom
Prior art keywords
dichloro
chloro
acridine
oxide
phenyl
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
GB474756A
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
Priority to GB797158A priority Critical patent/GB799366A/en
Priority to GB474756A priority patent/GB799361A/en
Priority to FR731557A priority patent/FR1269560A/en
Priority to DEP17945A priority patent/DE1109689B/en
Publication of GB799361A publication Critical patent/GB799361A/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)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)

Abstract

The invention comprises acridine-10-oxides of the general formula <FORM:0799361/IV (b)/1> and acid addition salts thereof, wherein R represents a divalent alkyl or hydroxyalkyl radical containing 2 to 5 carbon atoms, R1 and R2 are the same or different and each represent hydrogen or a normal or branched chain alkyl or hydroxy-alkyl radicals containing 2 to 8 carbon atoms or taken together with the nitrogen atom to which they are attached represent a saturated heterocyclic radical, and Y represents hydrogen or chlorine, or a methyl, phenyl or nitro group in the 2- or 3-position, and the preparation thereof by condensing the corresponding 6,9 - dichloroacridine - 10 - oxide with an aminoalkylamine of the general formula <FORM:0799361/IV (b)/2> or an acid addition salt thereof, R1 and R2 having the above significance, the said amine or acid addition salt being in excess of that required for the reaction or the condensation being carried out in the presence of an anhydrous organic solvent. It is preferable to use substantially equivalent quantities of reactants. Phenols, aliphatic alcohols, aliphatic ketones, aliphatic ethers, cyclic ethers and hydrocarbons are suitable solvents. The desired acridine-10-oxide may be recovered in its free base form by neutralizing the hydrochloride salt initially produced by the condensation reaction. When R1 and R2 together with the nitrogen atom to which they are attached represent a saturated heterocyclic group. The group may be a piperidino, morpholino, hexamethyleneimino, piperazino or pyrrolidino group. Suitable 6,9-dichloroacridine-10-oxide reactants are 3,9-dichloro-, 3,6,9-trichloro-, 3,9-dichloro-6-methyl-, 6,9 - dichloro - 2 - phenyl-, and 6,9-dichloro - 3 - nitro - acridine - 10 - oxides. In the examples the following compounds are prepared: 3,6 - dichloro - 9 - (4 - diethylamino - 1 - methylbutylamino)-acridine 10-oxide dihydrochloride and the corresponding 9-(5-piperidinopentylamino)-, 9 -(3 - piperazinopropylamino)-, and 9 - (3 - piperidinopropylamino) - compounds, 6 - chloro - 9 - (4 - diethylamino - 1 - methylbutylamino - 3 - methylacridine 10 - oxide dihydrochloride and the corresponding 2-phenyl compound, 3 - chloro - 9 - (4 - diethylamino - 1 - methylbutylamino) acridine 10-oxide dihydrochloride and the corresponding 9-(5-pyrrolidinopentylamino) compound, 2,21 - [3 - (3,6 - di - chloro - 9 - acridinylamino) propylimino) diethanol, and 2 - [4 - (6 - chloro - 3 - nitro - 9 - acridinylamino) - 4 - methylbutyl]ethylaminoethanol 10-oxide dihydrochloride. Starting compounds. 3,6,9 - Trichloro-, 3,9-dichloro-, 3,9 - dichloro - 6 - methyl-, 2 - phenyl-6,9 - dichloro- and 3 - nitro - 6,9 - dichloro-acridine 10-oxides are prepared by treating the corresponding free chloro-substituted acridines with perbenzoic acid in chloroform at room temperature. 3,9 - Dichloro - 6 - methyl-, 2-phenyl - 6,9 - dichloro- and 3 - nitro - 6,9 - dichloro-acridine are prepared by reacting 2,4-dichlorobenzoic acid and m-toluidine, 4-aminodiphenyl and m-nitroaniline to form 4-chloro-N-(m - tolyl) - anthranilic acid, 4 - chloro - N - (41-diphenyl) - anthranilic acid, and 4 - chloro - N - (m-nitrophenyl)-anthranilic acid respectively, and then treating these compounds with phosphorus oxychloride.
GB474756A 1956-02-15 1956-02-15 Acridine compounds and the preparation thereof Expired GB799361A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
GB797158A GB799366A (en) 1956-02-15 1956-02-15 Process for the preparation of acridine compounds
GB474756A GB799361A (en) 1956-02-15 1956-02-15 Acridine compounds and the preparation thereof
FR731557A FR1269560A (en) 1956-02-15 1957-02-12 Manufacturing process of organic acridine compounds
DEP17945A DE1109689B (en) 1956-02-15 1957-02-12 Process for the preparation of 6-chloro-9-aminoalkylamino-acridine-10-oxide compounds

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
GB799361A true GB799361A (en) 1958-08-06

Family

ID=9783019

Family Applications (2)

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

Family Applications Before (1)

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

Country Status (2)

Country Link
DE (1) DE1109689B (en)
GB (2) GB799366A (en)

Cited By (2)

* 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
US3694448A (en) * 1968-08-31 1972-09-26 Andrzej Ledochowski 1-nitro-9-(dialkylaminoalkylamino)acridine n{11 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 (2)

* 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
US3694448A (en) * 1968-08-31 1972-09-26 Andrzej Ledochowski 1-nitro-9-(dialkylaminoalkylamino)acridine n{11 oxides

Also Published As

Publication number Publication date
GB799366A (en) 1958-08-06
DE1109689B (en) 1961-06-29

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