GB1113804A - Creation of Inventions and Patents with Artificial Intelligence

GB1113804A – Improvements in or relating to substituted quinolines and the manufacture thereof
– Google Patents

GB1113804A – Improvements in or relating to substituted quinolines and the manufacture thereof
– Google Patents
Improvements in or relating to substituted quinolines and the manufacture thereof

Info

Publication number
GB1113804A

GB1113804A
GB5237867A
GB5237867A
GB1113804A
GB 1113804 A
GB1113804 A
GB 1113804A
GB 5237867 A
GB5237867 A
GB 5237867A
GB 5237867 A
GB5237867 A
GB 5237867A
GB 1113804 A
GB1113804 A
GB 1113804A
Authority
GB
United Kingdom
Prior art keywords
methyl
chloro
quinoline
amino
formula
Prior art date
1964-06-01
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
GB5237867A
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.)

University of Michigan

Original Assignee
University of Michigan
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.)
1964-06-01
Filing date
1965-05-21
Publication date
1968-05-15

1965-05-21
Application filed by University of Michigan
filed
Critical
University of Michigan

1968-05-15
Publication of GB1113804A
publication
Critical
patent/GB1113804A/en

Status
Expired
legal-status
Critical
Current

Links

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Global Dossier

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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

C07D215/38—Nitrogen atoms

C07D215/42—Nitrogen atoms attached in position 4

C07D215/44—Nitrogen atoms attached in position 4 with aryl radicals attached to said nitrogen atoms

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07D—HETEROCYCLIC COMPOUNDS

C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems

C07D215/38—Nitrogen atoms

C07D215/40—Nitrogen atoms attached in position 8

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07D—HETEROCYCLIC COMPOUNDS

C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems

C07D215/38—Nitrogen atoms

C07D215/42—Nitrogen atoms attached in position 4

C07D215/46—Nitrogen atoms attached in position 4 with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms

Abstract

Novel 7 – chloro – 4 – (1 – methyl – 2 – piperidinylmethylamino) – quinoline, 7 – chloro – 4 – (1 – methyl – 3 – piperidinylmethylamino)-quinoline, 7 – chloro – 4 – (4 – amino – 4 – methylpentylamino) – quinoline, 4 – substituted – 7 – chloroquinolines of the formula wherein R1 and R2 are lower alkyl radicals containing from 1 to 4 carbon atoms or R1 and R2, taken together with the N atom to which they are attached, form a pyrrolidino, piperidino or morpholino ring, and pharmaceutically acceptable acid addition salts thereof are prepared by condensation of 2-aminomethyl-1-methylpiperidine, 3 – amino – methyl – 1 – methylpiperidine, 1 – amino – 4 – methyl – 4 – nitropentane or a 1 – amino – 4 – methyl – 4 – aminopentane derivative of the formula respectively, with 7-chloro-4-phenoxyquinoline hydrochloride; followed by hydrogenation, in the case of 7-chloro-4-(4-amino-4-methylpentylamino)-quinoline, of the resulting 7-chloro-4-(4-methyl-4-nitropentylamino)-quinoline; followed by optional conversion to a pharmaceutically acceptable acid addition salt of the product. Pharmaceutical compositions, having anti-inflammatory and anti-amebic activity and being useful in the treatment of malarial infections, comprise as active ingredient 7-chloro-4 – (1 – methyl – 2 – piperidinylmethylamino)-quinoline, 7 – chloro – 4 – (1 – methyl – 3 – piperidinylmethylamino) – quinoline, 7 – chloro – 4 – (4-amino – 4 – methylpentylamino) – quinoline, a 4 – substituted – 7 – chloro – quinoline of the first formula above, or a pharmaceutically acceptable acid addition salt thereof, together with a pharmaceutically acceptable carrier. 2 – Aminomethyl – 1 – methylpiperidine is prepared by treating 2-(acetamidomethyl)-pyridine with iodomethane, converting the resulting 2-(acetamidomethyl) – 1 – methylpyridinium iodide to the corresponding chloride with silver chloride, reducing the chloride to give 2-(acetamidomethyl) – 1 – methylpiperidine and finally hydrolysing. 1 – Amino – 4 – methyl – 4 – nitropentane is prepared by reacting 1-bromo-4-methyl – 4 – nitropentane with potassium phthalimide and treating the resulting 4-methyl-4 – nitro – 1 – phthalimidopentane with hydrazine hydrate. 1 – Amino – 4 – methyl – 4 – aminopentane derivatives of the second formula above are prepared by reacting 2,5-dibromo-2-methylpentane with potassium phthalimide, reacting the 4 – bromo – 4 – methyl – 1 – phthalimidopentane so obtained with a secondary amine of the formula R1R2NH and then treating the resulting phthalimide of the formula with hydrazine hydrate.

GB5237867A
1964-06-01
1965-05-21
Improvements in or relating to substituted quinolines and the manufacture thereof

Expired

GB1113804A
(en)

Applications Claiming Priority (1)

Application Number
Priority Date
Filing Date
Title

US37181164A

1964-06-01
1964-06-01

Publications (1)

Publication Number
Publication Date

GB1113804A
true

GB1113804A
(en)

1968-05-15

Family
ID=23465490
Family Applications (3)

Application Number
Title
Priority Date
Filing Date

GB5237767A
Expired

GB1113803A
(en)