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GB1280203A - Quinoline derivatives and a process for the preparation thereof - Google Patents

Quinoline derivatives and a process for the preparation thereof

Info

Publication number
GB1280203A
GB1280203A GB57018/71A GB5701871A GB1280203A GB 1280203 A GB1280203 A GB 1280203A GB 57018/71 A GB57018/71 A GB 57018/71A GB 5701871 A GB5701871 A GB 5701871A GB 1280203 A GB1280203 A GB 1280203A
Authority
GB
United Kingdom
Prior art keywords
benzoyl
ester
quinoline derivatives
piperidineacetic
acid
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
GB57018/71A
Inventor
J A W Gutzwiller
M R Uskokovic
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB1280203A publication Critical patent/GB1280203A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic 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
    • C07D471/02Heterocyclic 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
    • C07D471/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00Carboxylic acid nitriles
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D211/00Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06Heterocyclic 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
    • C07D211/08Heterocyclic 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
    • C07D211/18Heterocyclic 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
    • C07D211/30Heterocyclic 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
    • C07D211/32Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D211/00Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06Heterocyclic 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
    • C07D211/08Heterocyclic 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
    • C07D211/18Heterocyclic 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
    • C07D211/34Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D211/00Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68Heterocyclic 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
    • C07D211/72Heterocyclic 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
    • C07D211/74Oxygen atoms
    • C07D211/76Oxygen atoms attached in position 2 or 6
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D211/00Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/92Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
    • C07D211/94Oxygen atom, e.g. piperidine N-oxide
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D217/00Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02Heterocyclic 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
    • C07D217/06Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D453/00Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • C07D453/04Heterocyclic 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
    • HELECTRICITY
    • H02GENERATION; CONVERSION OR DISTRIBUTION OF ELECTRIC POWER
    • H02JCIRCUIT ARRANGEMENTS OR SYSTEMS FOR SUPPLYING OR DISTRIBUTING ELECTRIC POWER; SYSTEMS FOR STORING ELECTRIC ENERGY
    • H02J50/00Circuit arrangements or systems for wireless supply or distribution of electric power
    • H02J50/30Circuit arrangements or systems for wireless supply or distribution of electric power using light, e.g. lasers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Computer Networks & Wireless Communication (AREA)
  • Power Engineering (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

1280203 Quinoline derivatives F HOFFMANN-LA ROCHE & CO AG 2 July 1969 [2 July 1968] 57018/71 Divided out of 1280201 Heading C2C Novel quinoline derivatives of the Formulae Ia and Ib wherein R 1 is H, OH, halogen, C 1-7 alkyl, C 1-7 alkoxy or methylenedioxy, R 2 is vinyl or C 1-7 alkyl, R 4 is H or acyl, and m is 1 or 2, with the proviso that when R 1 is methylenedioxy m is 1, their antipodes and racemates and acid addition salts thereof are prepared by condensing the corresponding 4-methylquinolines with compounds of the Formulµ IIIa and IIIb wherein R 3 is C 1-7 alkyl, and, if desired, converting the bases so obtained into acid addition salts. The following starting materials and intermediates are prepared: 2-benzoyl-octahydro- 6(2H) - isoquinoline 2<SP>1</SP> - benzoyl - 4,5 - dimethyl- 1<SP>1</SP>,2<SP>1</SP>,3<SP>1</SP>,4<SP>1</SP>,4<SP>1</SP>a,7<SP>1</SP>,8<SP>1</SP>,8<SP>1</SP>a - octahydrospiro- [1,3- dioxolane - 2,6<SP>1</SP>(5<SP>1</SP>H) - isoquinoline 7 - benzoyldecahydro - 2H - pyrido[3,4 - d]azepine - 2 - one, 2 - benzoyl - 1,2,3,4,7,8,9,9a - octahydro - 6H- pyrido[3,4 - d]azepine - 6 - one, 1 - benzoyl - 3- (2 - aminoethyl) - 4 - piperidineacetic acid ethyl ester, 1 - benzoyl - 3 - vinyl - 4 - piperidineacetic acid ethyl ester, 1 - benzoyl - 3 - (2 - dimethylaminoethyl)-4-piperidineacetic acid ethyl ester and its N-oxide, 7-benzoyl-3-nitroso-decahydro- 2H - pyrido[3,4 - d]azepin - 2 - one, 1 benzoyl. 3 - vinyl - 4 - piperidineacetic acid and its methyl ester, 3 - (α - benzyloxycarbonylcyanomethyl)glutaric acid diethyl ester, 3-(1- benzyloxycarbonyl - 1 - cyanopropyl)glutaric acid diethyl ester, 3- (1 .cyanopropyl)glutaric acid diethyl ester, 4-ethoxycarbonylmethyl-S-ethyl- 2 - piperdone, 3 - ethyl - 4 - piperidineacetic acid ethyl ester and 3-ethyl-4-ethoxycarbonyl- 6-ethoxy-1,2,3,4-tetrahydropyridine. Pharmaceutical compositions, having antiarrhythmic activity and suitable for oral or parenteral administration, contain the above novel quinoline derivatives, their antipodes or racemates or acid addition salts thereof, in association with suitable carriers or diluents.
GB57018/71A 1968-07-02 1969-07-02 Quinoline derivatives and a process for the preparation thereof Expired GB1280203A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US74191468A 1968-07-02 1968-07-02

Publications (1)

Publication Number Publication Date
GB1280203A true GB1280203A (en) 1972-07-05

Family

ID=24982733

Family Applications (2)

Application Number Title Priority Date Filing Date
GB57018/71A Expired GB1280203A (en) 1968-07-02 1969-07-02 Quinoline derivatives and a process for the preparation thereof
GB33312/69A Expired GB1280201A (en) 1968-07-02 1969-07-02 Quinoline derivatives

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB33312/69A Expired GB1280201A (en) 1968-07-02 1969-07-02 Quinoline derivatives

Country Status (14)

Country Link
JP (1) JPS497160B1 (en)
AT (4) AT323337B (en)
BE (1) BE735451A (en)
CA (3) CA954516A (en)
CH (4) CH559181A5 (en)
DE (1) DE1933600A1 (en)
DK (1) DK129235B (en)
FR (2) FR2012152B1 (en)
GB (2) GB1280203A (en)
IE (3) IE33813B1 (en)
IL (4) IL32535A (en)
NL (1) NL162384C (en)
PH (3) PH11413A (en)
SE (3) SE364044B (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0030044A1 (en) * 1979-11-01 1981-06-10 Acf Chemiefarma Nv Quinoline derivatives, processes for their preparation, their use, pharmaceutical compositions containing them and a method for the preparation of these pharmaceutical compositions
US4357471A (en) 1976-12-17 1982-11-02 Rohm And Haas Company Azaspiro compounds
US4374991A (en) 1976-12-17 1983-02-22 Rohm And Haas Company 2,6-Dimethylpiperidinyl-N-carbobutoxymethyl urea
US4400512A (en) * 1976-12-17 1983-08-23 Rohm And Haas Company Azaspiro compounds
US4405630A (en) * 1980-12-29 1983-09-20 Rohm And Haas Company Arthropod repellent compositions and methods

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3857837A (en) * 1968-07-02 1974-12-31 Hoffmann La Roche Processes and intermediated for quinine, quinidine, isomers and derivatives thereof
JPS5147064U (en) * 1974-10-04 1976-04-07

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4357471A (en) 1976-12-17 1982-11-02 Rohm And Haas Company Azaspiro compounds
US4374991A (en) 1976-12-17 1983-02-22 Rohm And Haas Company 2,6-Dimethylpiperidinyl-N-carbobutoxymethyl urea
US4400512A (en) * 1976-12-17 1983-08-23 Rohm And Haas Company Azaspiro compounds
EP0030044A1 (en) * 1979-11-01 1981-06-10 Acf Chemiefarma Nv Quinoline derivatives, processes for their preparation, their use, pharmaceutical compositions containing them and a method for the preparation of these pharmaceutical compositions
US4405630A (en) * 1980-12-29 1983-09-20 Rohm And Haas Company Arthropod repellent compositions and methods

Also Published As

Publication number Publication date
FR2012152B1 (en) 1973-08-10
FR2108178B1 (en) 1974-03-22
PH10708A (en) 1977-08-24
IL43884A0 (en) 1974-03-14
IE33812B1 (en) 1974-11-13
GB1280201A (en) 1972-07-05
AT323338B (en) 1975-07-10
IE33814B1 (en) 1974-11-13
IL32535A (en) 1975-05-22
NL162384C (en) 1980-05-16
CA954517A (en) 1974-09-10
IL43886A0 (en) 1974-03-14
DK129235B (en) 1974-09-16
CH533622A (en) 1973-02-15
FR2012152A1 (en) 1970-03-13
IE33813B1 (en) 1974-11-13
NL6910136A (en) 1970-01-06
AT323337B (en) 1975-07-10
PH11413A (en) 1977-12-27
DK129235C (en) 1975-02-10
JPS497160B1 (en) 1974-02-19
SE364044B (en) 1974-02-11
AT319482B (en) 1974-12-27
CA954516A (en) 1974-09-10
IE33812L (en) 1970-01-02
PH10255A (en) 1976-10-14
SE376612B (en) 1975-06-02
NL162384B (en) 1979-12-17
IE33813L (en) 1970-01-02
IL32535A0 (en) 1969-09-25
CA974994A (en) 1975-09-23
SE375776B (en) 1975-04-28
IE33814L (en) 1970-01-02
DE1933600A1 (en) 1970-01-08
FR2108178A1 (en) 1972-05-19
CH559184A5 (en) 1975-02-28
CH559181A5 (en) 1975-02-28
IL43885A0 (en) 1974-03-14
CH559183A5 (en) 1975-02-28
BE735451A (en) 1970-01-02
AT300813B (en) 1972-07-15

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee