IE35953B1 - Quinoline derivatives - Google Patents

Quinoline derivatives

Info

Publication number
IE35953B1
IE35953B1 IE8/72A IE872A IE35953B1 IE 35953 B1 IE35953 B1 IE 35953B1 IE 8/72 A IE8/72 A IE 8/72A IE 872 A IE872 A IE 872A IE 35953 B1 IE35953 B1 IE 35953B1
Authority
IE
Ireland
Prior art keywords
formula
compound
ethyl
vinyl
quinoline
Prior art date
Application number
IE8/72A
Other versions
IE35953L (en
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of IE35953L publication Critical patent/IE35953L/en
Publication of IE35953B1 publication Critical patent/IE35953B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
    • C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D211/74—Oxygen atoms
    • C07D211/76—Oxygen atoms attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
    • C07D211/94—Oxygen atom, e.g. piperidine N-oxide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1347802 Trifluoromethyl-cinchonine type derivatives F HOFFMANN-LA ROCHE & CO AG 6 Jan 1972 [7 Jan 1971 (2)] 629/72 Heading C2C Novel compounds of the Formula (I) wherein R denotes vinyl or ethyl, their antipodes and racemates and acid addition salts thereof, may be obtained (a) by treating a compound of formula or an antipode or racemate thereofwith a stereoselective reducing agent, or (b) by hydrolyating a racemic or optically active compound, epimeric at positions 2 and 5, of the formula (III) or (c) by cyclizing a racemic or optically active compound of the Formula (IV) and, if desired, reducing R = vinyl to R = ethyl, if desired, resolving a racemate into its optical antipodes and, also if desired, converting a base obtained into an acid addition salt. Intermediates of Formula III are obtained by condensing a trifluoromethyl-4-methyl-quinoline with a 1-(H or acyl)-3 (R or S)-(vinyl or ethyl)-4(S)-piperidineacetic acid ester to yield a 4[3-[1-H or acyl)-3(R or S)-(vinyl or ethyl)- 4(S) - piperidyl] - 2 - oxopropyl] - quinoline (XII) which is reduced (if necessary, with deacylation to a corresponding 2-hydroxy propyl compound which may be converted to a 2-acyloxy compound and the 4-[3-[3-(R or S)- (vinyl or ethyl)-4(S)-piperidyl]-2#-(hydroxy or acyloxy) propyl] quinoline is converted to a compound III. Intermediates of Formula IV are obtained by halogenating a compound (XII) above to form a 4-[3-[1-acyl-3(R or S)-(vinyl or ethyl)-4(S)-piperidyl]-1# halo-2-oxopropyl]- quinoline which is reduced to a corresponding 1#,2#-oxapropyl compound and this is deacylated to yield (IV). Intermediates of Formula II and IIa can be obtained. by the following reaction scheme where R 1 and R 2 are C 1-7 alkyl Pharmaceutical compositions having antimalarial and antiarrhythmic properties comprise a compound of Formula I above together with the usual pharmaceutical adjuvants in forms suitable for oral or parenteral administration. [GB1347802A]
IE8/72A 1971-01-07 1972-01-04 Quinoline derivatives IE35953B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US10478571A 1971-01-07 1971-01-07
US10478471A 1971-01-07 1971-01-07

Publications (2)

Publication Number Publication Date
IE35953L IE35953L (en) 1972-07-07
IE35953B1 true IE35953B1 (en) 1976-07-07

Family

ID=26801932

Family Applications (1)

Application Number Title Priority Date Filing Date
IE8/72A IE35953B1 (en) 1971-01-07 1972-01-04 Quinoline derivatives

Country Status (15)

Country Link
JP (1) JPS5550029B1 (en)
AT (2) AT339510B (en)
AU (1) AU462429B2 (en)
BE (1) BE777746A (en)
CA (1) CA966837A (en)
CH (1) CH565792A5 (en)
DE (1) DE2200496A1 (en)
DK (1) DK136070B (en)
FR (1) FR2121667B1 (en)
GB (1) GB1347802A (en)
IE (1) IE35953B1 (en)
IL (1) IL38492A (en)
NL (1) NL7200269A (en)
PH (1) PH11625A (en)
SE (1) SE374921B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH605916A5 (en) * 1973-12-07 1978-10-13 Hoffmann La Roche

Also Published As

Publication number Publication date
SE374921B (en) 1975-03-24
IE35953L (en) 1972-07-07
NL7200269A (en) 1972-07-11
AT339510B (en) 1977-10-25
ATA575474A (en) 1976-11-15
ATA575274A (en) 1977-02-15
CA966837A (en) 1975-04-29
FR2121667B1 (en) 1975-02-07
BE777746A (en) 1972-07-06
DE2200496A1 (en) 1972-07-20
PH11625A (en) 1978-04-12
AT337913B (en) 1977-07-25
DK136070C (en) 1978-01-09
AU462429B2 (en) 1975-06-26
DK136070B (en) 1977-08-08
JPS5550029B1 (en) 1980-12-16
IL38492A (en) 1975-08-31
AU3762472A (en) 1973-07-12
IL38492A0 (en) 1972-03-28
GB1347802A (en) 1974-02-27
CH565792A5 (en) 1975-08-29
FR2121667A1 (en) 1972-08-25

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