GB614164A - Improvements in or relating to substituted acridines and process of making them - Google Patents

Improvements in or relating to substituted acridines and process of making them

Info

Publication number
GB614164A
GB614164A GB19323/45A GB1932345A GB614164A GB 614164 A GB614164 A GB 614164A GB 19323/45 A GB19323/45 A GB 19323/45A GB 1932345 A GB1932345 A GB 1932345A GB 614164 A GB614164 A GB 614164A
Authority
GB
United Kingdom
Prior art keywords
ethylamino
acridines
methoxy
prepared
general formula
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
GB19323/45A
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.)
Eli Lilly and Co
Original Assignee
Eli Lilly and Co
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 Eli Lilly and Co filed Critical Eli Lilly and Co
Publication of GB614164A publication Critical patent/GB614164A/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
    • C07D219/12—Amino-alkylamino radicals attached in position 9

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Cosmetics (AREA)

Abstract

2 - Methoxy - 6 - chloro - 9[21-(disubstituted-amino)ethylamino] acridines of the general formula <FORM:0614164/IV(b)/1> wherein R represents the same saturated non-tertiary hydrocarbon radical having from 3 to 7 carbon atoms, are prepared by reacting a secondary amine of the general formula <FORM:0614164/IV(b)/2> with sodium bisulphite, formaldehyde and potassium cyanide in aqueous solution to yield an aminoacetonitrile of the general formula <FORM:0614164/IV(b)/3> which is reduced to a substituted aminoethylamine of the general formula <FORM:0614164/IV(b)/4> and then condensed with 2-methoxy-6 : 9-dichloro-acridine. The aminoacetonitrile may be reduced to the substituted aminoethylamine by treatment with sodium in alcohol solution or an ether solution of the aminoacetonitrile to which a small quantity of liquid ammonia is added is reduced with hydrogen under heat and pressure in the presence of a hydrogenation catalyst, e.g. Raney nickel. In examples 1 to 9, the following substituted acridines and their dihydrochlorides, dihydrobromides, sulphates, lactates, nitrates, phosphates and propionates are prepared : 9 - [21 - (dicyclohexylamino) ethylamino]-, 9 - [21 - (di - isoamylamino) ethylamino]-, 9 - [21 - (di - n - amylamino) ethylamino]-, 9 - [21 - (di - n - butylamino) ethylamino]-, 9 - [21 - (di - isobutylamino) ethylamino]-, 9 - [21 - (di - n - propylamino) ethylamino]-, and 9 - [21 - (di - n - heptyl-amino)ethylamino] - 2 - methoxy - 6 - chloro-acridines. The following aminoacetonitriles are prepared : dicyclohexylamino-, di-isoamylamino-, di - n - amylamino -, di - n - butylamino-, di - isobutylamino-, di - n - propylamino- and di - n - heptylaminoacetonitriles. The following substituted-aminoethylamines are prepared : 2 - (dicyclohexylamino) -, 2 - (di - isoamylamino) -, 2 - (di - n - amylamino)-, 2 - (di - n - butylamino) -, 2 - (di - isobutylamino) -, 2 - (di - n - propylamino) - and 2 - (di - n - heptylamino)ethylamines. Specification 497,042 is referred to.ALSO:2 - Methoxy - 6 - chloro - 9 - [21 - (disubstituted - amino) ethylamino] acridines of the general formula <FORM:0614164/IV (c)/1> wherein R represents the same saturated nontertiary hydrocarbon radical having from 3 to 7 carbon atoms, are prepared by condensing <FORM:0614164/IV (c)/2> with 2 - methoxy - 6 : 9 - dichloro - acridine. In examples (1) to (9), the following substituted acridines and their dihydrochlorides, dihydrobromides, sulphates, lactates, nitrates, phosphates and propionates are prepared: 9-[21-(dicyclohexylamino) ethylamino]-, 9 - [21 - (di - isoamylamino) ethylamino]-, 9-[21-(di-n-amylamino) ethylamino]-, 9-[21-(di-n-butylamino) ethylamino]-, 9 - [21 - (di - isobutylamino) ethyl - amino]-9-[21-(di-n-propylamino) ethylamino]-, and 9-[21-(di-n-heptylamino) ethylamino]-2-methoxy - 6 - chloro - acridines. Specification 497,042 is referred to.
GB19323/45A 1944-07-29 1945-07-27 Improvements in or relating to substituted acridines and process of making them Expired GB614164A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US614164XA 1944-07-29 1944-07-29

Publications (1)

Publication Number Publication Date
GB614164A true GB614164A (en) 1948-12-10

Family

ID=22035639

Family Applications (1)

Application Number Title Priority Date Filing Date
GB19323/45A Expired GB614164A (en) 1944-07-29 1945-07-27 Improvements in or relating to substituted acridines and process of making them

Country Status (2)

Country Link
BE (1) BE614164A (en)
GB (1) GB614164A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2808067A1 (en) * 1977-03-03 1978-09-07 Parke Davis & Co N- (SUBSTITUTED AMINOALKYL) -2-OXO-1- PYRROLIDINE ACETAMIDE AND METHOD FOR THE PREPARATION
CN111170952A (en) * 2019-12-04 2020-05-19 武汉德克瑞生物医药科技有限公司 Synthesis process of 2-aminoquinazoline compound

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2808067A1 (en) * 1977-03-03 1978-09-07 Parke Davis & Co N- (SUBSTITUTED AMINOALKYL) -2-OXO-1- PYRROLIDINE ACETAMIDE AND METHOD FOR THE PREPARATION
CN111170952A (en) * 2019-12-04 2020-05-19 武汉德克瑞生物医药科技有限公司 Synthesis process of 2-aminoquinazoline compound

Also Published As

Publication number Publication date
BE614164A (en) 1962-06-18

Similar Documents

Publication Publication Date Title
US2966488A (en) Substituted alkylaminopurines
GB581994A (en) Amino ethers
GB823303A (en) Improvements in or relating to materials for cleansing the hair
GB614164A (en) Improvements in or relating to substituted acridines and process of making them
GB1094205A (en) Process for the preparation of amino-acid surface active agents
US2403713A (en) Preparation of 4-basically substituted 2-sulphanilamidopyrimidines
US2375735A (en) Preparation of pyrimidines
GB600851A (en) Production of substituted propyldiamines and particularly their acridine compounds
MURAOKA et al. Antiviral effect of alkylpyrimidine derivatives
GB602351A (en) Processes of making substituted acridines
US2025876A (en) Preparation of aryl-amines
GB604375A (en) Substituted acridines and intermediates therefor, and process of making them
GB569157A (en) Sulphanilamide derivatives
GB609488A (en) Production of propyldiamines and acridine compounds of propyldiamines
GB600841A (en) Processes of producing substituted acridines
GB607289A (en) Improvements in processes for producing substituted acridines
GB482126A (en) Improvements in the manufacture of alkylolamines
GB605870A (en) Improvements in or relating to process of producing substituted acridines and intermediates therefor
GB365535A (en) Manufacture of optically active 1-phenyl-2-amino-alcohols-(1)
GB648904A (en) Process for the manufacture of 2:4:5-triamino-6-hydroxy-pyrimidine
GB482580A (en) Improved manufacture of hydroaromatic nitrogen compounds
GB595472A (en) Improvements in or relating to the preparation of n-(para-aminobenzenesulphonyl)-guanidines
GB594949A (en) Improvements in and relating to the synthesis of riboflavin and intermediates therefor
GB1501070A (en) Preparation of 4,4&#39;-diaminostilbene-2,2&#39;-disulphonic acid or its alkali salts
GB666027A (en) New pyrimidine derivatives