GB1041697A

GB1041697A – Novel 6,7-dihydro-benzo[a]quinolizinium salts and a process for the preparation thereof
– Google Patents

GB1041697A – Novel 6,7-dihydro-benzo[a]quinolizinium salts and a process for the preparation thereof
– Google Patents
Novel 6,7-dihydro-benzo[a]quinolizinium salts and a process for the preparation thereof

Info

Publication number
GB1041697A

GB1041697A
GB45824/65A
GB4582465A
GB1041697A
GB 1041697 A
GB1041697 A
GB 1041697A
GB 45824/65 A
GB45824/65 A
GB 45824/65A
GB 4582465 A
GB4582465 A
GB 4582465A
GB 1041697 A
GB1041697 A
GB 1041697A
Authority
GB
United Kingdom
Prior art keywords
benzo
dihydro
quinolizinium
preparation
novel
Prior art date
1963-06-07
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
GB45824/65A
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.)
1963-06-07
Filing date
1964-06-05
Publication date
1966-09-07

1963-06-07
Priority claimed from CH704063A
external-priority
patent/CH450414A/en

1964-06-05
Application filed by F Hoffmann La Roche AG
filed
Critical
F Hoffmann La Roche AG

1966-09-07
Publication of GB1041697A
publication
Critical
patent/GB1041697A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

QCRCVAMGUZYIKG-UHFFFAOYSA-N
6,7-dihydrobenzo[a]quinolizin-5-ium
Chemical class

C1=CC=C2CC[N+]3=CC=CC=C3C2=C1
QCRCVAMGUZYIKG-UHFFFAOYSA-N
0.000
title
abstract
2

SWYGQBOAPWEUMR-UHFFFAOYSA-N
2,3,4,6-tetrahydro-1H-benzo[a]quinolizine
Chemical compound

C1CCCN2CC=C3C(=C12)C=CC=C3
SWYGQBOAPWEUMR-UHFFFAOYSA-N
0.000
abstract
1

-1
2-carboxymethyl-3-ethyl-9,10-dimethoxy-6,7-dihydro-benzo -[a]-quinolizinium cation
Chemical class

0.000
abstract
1

YDZIFJMWOCAKAO-UHFFFAOYSA-N
3-ethyl-9,10-dimethoxy-2-methyl-6,7-dihydrobenzo[a]quinolizin-5-ium
Chemical compound

CC=1C(=C[N+]=2CCC3=C(C2C1)C=C(C(=C3)OC)OC)CC
YDZIFJMWOCAKAO-UHFFFAOYSA-N
0.000
abstract
1

125000000217
alkyl group
Chemical group

0.000
abstract
1

125000004432
carbon atom
Chemical group

C*

0.000
abstract
1

125000003178
carboxy group
Chemical group

[H]OC(*)=O

0.000
abstract
1

150000001768
cations
Chemical class

0.000
abstract
1

125000001301
ethoxy group
Chemical group

[H]C([H])([H])C([H])([H])O*

0.000
abstract
1

125000004435
hydrogen atom
Chemical group

[H]*

0.000
abstract
1

BRMYZIKAHFEUFJ-UHFFFAOYSA-L
mercury diacetate
Chemical compound

CC(=O)O[Hg]OC(C)=O
BRMYZIKAHFEUFJ-UHFFFAOYSA-L
0.000
abstract
1

125000000956
methoxy group
Chemical group

[H]C([H])([H])O*

0.000
abstract
1

230000003647
oxidation
Effects

0.000
abstract
1

238000007254
oxidation reaction
Methods

0.000
abstract
1

230000001590
oxidative effect
Effects

0.000
abstract
1

150000003839
salts
Chemical class

0.000
abstract
1

Classifications

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07D—HETEROCYCLIC COMPOUNDS

C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine

C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine

C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine

C07D455/06—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine containing benzo [a] quinolizine ring systems

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07D—HETEROCYCLIC COMPOUNDS

C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine

C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine

C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine

C07D455/06—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine containing benzo [a] quinolizine ring systems

C07D455/08—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine containing benzo [a] quinolizine ring systems having an isoquinolyl-1, a substituted isoquinolyl-1 or an alkylenedioxyisoquinolyl-1 radical linked through only one carbon atom, attached in position 2, e.g. emetine

Abstract

The invention comprises 6,7-dihydro-benzo-[a]-quinolizinium salts having a cation of formula in which R represents an alkyl group having 1-4 carbon atoms, R1 and R2 represent methoxy or ethoxy groups, and X represents a hydrogen atom or carboxyl group, and the preparation thereof by oxidizing the corresponding tetrahydro-benzo-[a]-quinolizine. The oxidation is conveniently carried out using mercuric acetate. Preferred salts have the 2-methyl-3-ethyl-9,10 -dimethoxy-6,7-dihydro-benzo-[a]-quinolizinium or 2-carboxymethyl-3-ethyl-9,10-dimethoxy-6,7-dihydro-benzo -[a]-quinolizinium cation.

GB45824/65A
1963-06-07
1964-06-05
Novel 6,7-dihydro-benzo[a]quinolizinium salts and a process for the preparation thereof

Expired

GB1041697A
(en)

Applications Claiming Priority (2)

Application Number
Priority Date
Filing Date
Title

CH704063A

CH450414A
(en)

1963-06-07
1963-06-07

Process for the preparation of benzo (a) quinolizine derivatives

CH704163A

CH442316A
(en)

1963-06-07
1963-06-07

Process for the preparation of benzo (a) quinolizine derivatives

Publications (1)

Publication Number
Publication Date

GB1041697A
true

GB1041697A
(en)

1966-09-07

Family
ID=25700619
Family Applications (6)

Application Number
Title
Priority Date
Filing Date

GB45825/65A
Expired

GB1041698A
(en)

1963-06-07
1964-06-05
Novel 3,4-dihydro-isoquinolinium salts

GB23336/64A
Expired

GB1041696A
(en)

1963-06-07
1964-06-05
Manufacture of benzo[a]quinolizines

GB45824/65A
Expired

GB1041697A
(en)

1963-06-07
1964-06-05
Novel 6,7-dihydro-benzo[a]quinolizinium salts and a process for the preparation thereof

GB18814/66A
Expired

GB1041699A
(en)

1963-06-07
1964-06-05
Novel tetrahydro isoquinolinyl-methyldihydrobenzo[a]quinolizinium salts

GB23337/64A
Expired

GB1042205A
(en)

1963-06-07
1964-06-05
Manufacture of benzo[a]quinolizines

GB46933/65A
Expired

GB1042206A
(en)

1963-06-07
1964-06-05
Benzo[a]quinolizine amides and the preparation thereof

Family Applications Before (2)

Application Number
Title
Priority Date
Filing Date

GB45825/65A
Expired

GB1041698A
(en)

1963-06-07
1964-06-05
Novel 3,4-dihydro-isoquinolinium salts

GB23336/64A
Expired

GB1041696A
(en)

1963-06-07
1964-06-05
Manufacture of benzo[a]quinolizines

Family Applications After (3)

Application Number
Title
Priority Date
Filing Date

GB18814/66A
Expired

GB1041699A
(en)

1963-06-07
1964-06-05
Novel tetrahydro isoquinolinyl-methyldihydrobenzo[a]quinolizinium salts

GB23337/64A
Expired

GB1042205A
(en)

1963-06-07
1964-06-05
Manufacture of benzo[a]quinolizines

GB46933/65A
Expired

GB1042206A
(en)

1963-06-07
1964-06-05
Benzo[a]quinolizine amides and the preparation thereof

Country Status (8)

Country
Link

US
(1)

US3359264A
(en)

BE
(2)

BE648824A
(en)

BR
(2)

BR6459690D0
(en)

CH
(1)

CH442316A
(en)

DK
(1)

DK123358B
(en)

GB
(6)

GB1041698A
(en)

NL
(2)

NL6405025A
(en)

SE
(2)

SE326448B
(en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

GB1059326A
(en)

*

1962-10-31
1967-02-15
Glaxo Lab Ltd
Reactions and intermediates of use in syntheses of compounds of the 2-dehydroemetine series

US4133812A
(en)

*

1975-11-21
1979-01-09
Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt.
Process for producing benzo (a) quinolizine derivatives

USD435684S
(en)

2000-02-08
2000-12-26
Gary Products Group, Inc.
Tube light surface clip

Family Cites Families (4)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US3159638A
(en)

*

1964-12-01

Xcha-chj

US3105835A
(en)

*

1963-10-01

Isoquinoline derivatives

US3240782A
(en)

*

1966-03-15

Method of converting z-dehydro-isoeme
tine into z-dehydro-emetine and inter-
mediates therein

GB977789A
(en)

*

1960-12-02
1964-12-16
Glaxo Group Ltd
Emetine derivatives and their preparation

1963

1963-06-07
CH
CH704163A
patent/CH442316A/en
unknown

1964

1964-05-06
NL
NL6405025A
patent/NL6405025A/xx
unknown

1964-05-11
SE
SE05726/64A
patent/SE326448B/xx
unknown

1964-05-21
NL
NL6405645A
patent/NL125065C/xx
active

1964-06-03
SE
SE6717/64A
patent/SE315284B/xx
unknown

1964-06-03
BR
BR159690/64A
patent/BR6459690D0/en
unknown

1964-06-03
BR
BR159689/64A
patent/BR6459689D0/en
unknown

1964-06-04
BE
BE648824D
patent/BE648824A/xx
unknown

1964-06-04
BE
BE648823D
patent/BE648823A/fr
unknown

1964-06-05
GB
GB45825/65A
patent/GB1041698A/en
not_active
Expired

1964-06-05
GB
GB23336/64A
patent/GB1041696A/en
not_active
Expired

1964-06-05
GB
GB45824/65A
patent/GB1041697A/en
not_active
Expired

1964-06-05
GB
GB18814/66A
patent/GB1041699A/en
not_active
Expired

1964-06-05
US
US373043A
patent/US3359264A/en
not_active
Expired – Lifetime

1964-06-05
GB
GB23337/64A
patent/GB1042205A/en
not_active
Expired

1964-06-05
GB
GB46933/65A
patent/GB1042206A/en
not_active
Expired

1964-06-08
DK
DK285364AA
patent/DK123358B/en
unknown

Also Published As

Publication number
Publication date

GB1041696A
(en)

1966-09-07

SE315284B
(en)

1969-09-29

BR6459689D0
(en)

1973-08-02

US3359264A
(en)

1967-12-19

BE648824A
(en)

1964-12-04

SE326448B
(en)

1970-07-27

BE648823A
(en)

1964-12-04

GB1042206A
(en)

1966-09-14

GB1042205A
(en)

1966-09-14

GB1041699A
(en)

1966-09-07

BR6459690D0
(en)

1973-08-02

DE1445895A1
(en)

1969-11-27

NL6405645A
(en)

1964-12-08

NL125065C
(en)

1968-04-16

GB1041698A
(en)

1966-09-07

DK123358B
(en)

1972-06-12

CH442316A
(en)

1967-08-31

NL6405025A
(en)

1964-12-08

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