IE33474B1 - A process for the manufacture of quinoline derivatives - Google Patents

A process for the manufacture of quinoline derivatives

Info

Publication number
IE33474B1
IE33474B1 IE903/69A IE90369A IE33474B1 IE 33474 B1 IE33474 B1 IE 33474B1 IE 903/69 A IE903/69 A IE 903/69A IE 90369 A IE90369 A IE 90369A IE 33474 B1 IE33474 B1 IE 33474B1
Authority
IE
Ireland
Prior art keywords
propionic acid
chloro
ethyl ester
benzoyl
compounds
Prior art date
Application number
IE903/69A
Other versions
IE33474L (en
Inventor
J A W Gutzwiller
M R Uskovic
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 IE33474L publication Critical patent/IE33474L/en
Publication of IE33474B1 publication Critical patent/IE33474B1/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
    • 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
    • C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
    • 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

Landscapes

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

Abstract

1,253,741. Quinoline derivatives. F. HOFFMANN-LA ROCHE & CO. A.G. 2 July, 1969 [2 July, 1968], No. 33311/69. Heading C2C. Quinoline derivatives of the Formulµ I and II: wherein E 1 is H, OH, halogen, C 1-7 alkyl, C 1-7 alkoxy or methylenedioxy, R 2 is C 1-7 alkyl or C 2-7 alkenyl and m is 1 or 2, with the proviso that when R 1 is methylenedioxy m is 1, the compounds of Formulµ I and II being novel provided that when (R 1 ) m is H, OH or C 1-7 alkoxy in position 6, R 2 is other than vinyl or ethyl, and their antipodes and racemates and acid addition salts thereof are prepared by treating compounds of Formulµ V and VI: these compounds being novel provided that when (R 1 ) m is H, OH or OCH 3 in position- 6, R 2 is other than vinyl or ethyl, their racemates or antipodes thereof with a stereoselective reducing agent, if desired reducing any compound obtained in which R 2 is C 2-7 alkenyl to give corresponding compounds in which R 2 is C 2-7 alkyl, and also, if desired, converting bases obtained into acid addition salts. Compounds of Formulµ V and VI above are obtained by cyclizing compounds of the general Formula IV: X is halogen, with the proviso that when (R 1 ) m is H or OCH 3 in position 6 and R 2 is vinyl or ethyl, X is other than bromine, or antipodes or racemates thereof, or compound of general Formula X above, where R<SP>1</SP> 2 is C 1-7 alkyl or antipodes or racemates thereof, or compounds of the general Formula X above, wherein R is H or C 1-5 alkyl or antipodes or racemates thereof, by means of a cyclization agent, dehalogenating the product obtained from compounds of Formula Xa or antipodes or racemates thereof and, if desired, converting the so-obtained bases into acid addition salts. The following intermediates are prepared:- α - [1 - Benzoyl - 3 - ethyl - 4 - piperidylmethyl]- # - oxo - # - (7 - methoxy - 4 - quinolyl)propionic acid ethyl ester, α-[1-benzoyl-3-ethyl-4-piperidylmethyl] - # - oxo - # - (6,7 - dimethoxy - 4- quinolyl)propionic acid ethyl ester, α-[1-benzoyl - 3 - ethyl - 4 - piperidylmethyl] - # - oxo - #- (6 - methyl - 4 - quinolyl)propionic acid ethyl ester, α - [1 - benzoyl - 3 - ethyl - 4 - piperidylmethyl] - # - oxo - # - (6 - chloro - 4 - quinolyl)propionic acid ethyl ester, α-[l-benzoyl-3-ethyl-4- piperidylmethyl] - # - oxo - # - (7 - chloro - 4- quinolyl)propionic acid ethyl ester, α-[1-benzoyl - 3 - vinyl - 4 - piperidylmethyl]- # - oxo - #- (7 - chloro - 4 - quinolyl)propionic acid ethyl ester, 7<SP>1</SP> - methoxydihydrocinchotoxine, 6<SP>1</SP>,7<SP>1</SP>- dimethoxy - dihydrocinchotoxine, 6<SP>1</SP> - dimethyldihydrocinchotoxine, 6<SP>1</SP> - chlorodihydrocinchotoxine, 7<SP>1</SP> - chlorodihydrocinchotoxine, 7<SP>1</SP>- chlorocinchotoxine, N - chlorodihydroquinotoxine, N - chloro - 7<SP>1 </SP>- methoxydihydrocinchotoxine, N - chloroquinotoxine, N - chloro - 6<SP>1</SP>,7<SP>1</SP>- dimethoxydihydrocinchotoxine, N - chloro- 6<SP>1</SP> - methyldihydrocinchotoxine, N - chloro - 6<SP>1</SP>- chlorodihydrocinchotoxine, N - chloro - 7<SP>1</SP>- chlorodihydrocinchotoxine, N - chloro - 7<SP>1</SP>- chlorocinchotoxine, 3 - (1 - chloro - 3 - ethyl- 4 - piperidine)propionic acid ethyl ester, 3- [3 - (2 - chloroethyl) - 4 - piperidine]propionic acid ethyl ester trifluoroacetate, 3-[1-benzoyl-3- (2 - chloroethyl) - 4 - piperidine]propionic acid ethyl ester, 3-[1-benzoyl-3-(2-iodoethyl)-4-piperidine]propionic acid ethyl ester, and 3-[1- benzoyl - 3 - vinyl - 4 - piperidine]propionic acid ethyl ester. The above intermediates are obtained in one or more of the possible configurations. Pharmaceutical compositions, having antimalarial and antiarrhythmic properties, contain the above novel compounds of Formulµ I, II, V and VI, or acid addition salts thereof, in association with compatible pharmaceutical carriers. The compositions may be in a forms suitable for oral, parenteral or rectal administration. [GB1253741A]
IE903/69A 1968-07-02 1969-07-02 A process for the manufacture of quinoline derivatives IE33474B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US74191368A 1968-07-02 1968-07-02

Publications (2)

Publication Number Publication Date
IE33474L IE33474L (en) 1970-01-02
IE33474B1 true IE33474B1 (en) 1974-07-10

Family

ID=24982727

Family Applications (1)

Application Number Title Priority Date Filing Date
IE903/69A IE33474B1 (en) 1968-07-02 1969-07-02 A process for the manufacture of quinoline derivatives

Country Status (14)

Country Link
JP (1) JPS4915278B1 (en)
AT (2) AT319481B (en)
BE (1) BE735450A (en)
CA (2) CA956312A (en)
CH (2) CH533123A (en)
DE (2) DE1967178C2 (en)
DK (2) DK136069B (en)
FR (1) FR2012151A1 (en)
GB (1) GB1253741A (en)
IE (1) IE33474B1 (en)
IL (1) IL32534A (en)
NL (1) NL166475C (en)
PH (1) PH12608A (en)
SE (2) SE367823B (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH590274A5 (en) * 1970-03-16 1977-07-29 Hoffmann La Roche
GB1441244A (en) * 1972-11-17 1976-06-30 Rech Et Dapplications Scient S Derivatives of quinoline and method of preparing the same
NL7908031A (en) * 1979-11-01 1981-06-01 Acf Chemiefarma Nv NEW QUINOLINE DERIVATIVES AND PHARMACEUTICAL PREPARATIONS CONTAINING SUCH A COMPOUND AND METHOD FOR PREPARING THESE COMPOUNDS.
FR2844270B1 (en) 2002-09-11 2006-05-19 Aventis Pharma Sa QUINOLYL PROPYL PIPERIDINE DERIVATIVES, THEIR PROCESS AND PREPARATION INTERMEDIATES AND THE COMPOSITIONS CONTAINING THEM
AU2011202542A1 (en) 2010-07-14 2012-02-02 Indian Institute Of Science Benzothiophene carboxamide compounds, composition and applications thereof

Also Published As

Publication number Publication date
ATA49171A (en) 1977-05-15
IL32534A0 (en) 1969-09-25
DE1967178C2 (en) 1984-11-22
DE1933599A1 (en) 1970-02-26
CA956312A (en) 1974-10-15
DK136982C (en) 1978-07-10
NL166475B (en) 1981-03-16
IE33474L (en) 1970-01-02
AT319481B (en) 1974-12-27
PH12608A (en) 1979-06-27
BE735450A (en) 1970-01-02
SE367823B (en) 1974-06-10
GB1253741A (en) 1971-11-17
DK136069C (en) 1978-01-16
NL166475C (en) 1981-08-17
CH521975A (en) 1972-04-30
AT341115B (en) 1978-01-25
DK136069B (en) 1977-08-08
DK136982B (en) 1977-12-27
FR2012151A1 (en) 1970-03-13
CA962682A (en) 1975-02-11
CH533123A (en) 1973-01-31
JPS4915278B1 (en) 1974-04-13
SE375775B (en) 1975-04-28
NL6910144A (en) 1970-01-06
IL32534A (en) 1975-07-28

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