GB1070308A

GB1070308A – Pyridyl dihydroisoquinolines
– Google Patents

GB1070308A – Pyridyl dihydroisoquinolines
– Google Patents
Pyridyl dihydroisoquinolines

Info

Publication number
GB1070308A

GB1070308A
GB12886/66A
GB1288666A
GB1070308A
GB 1070308 A
GB1070308 A
GB 1070308A
GB 12886/66 A
GB12886/66 A
GB 12886/66A
GB 1288666 A
GB1288666 A
GB 1288666A
GB 1070308 A
GB1070308 A
GB 1070308A
Authority
GB
United Kingdom
Prior art keywords
formula
alkyl
compound
cyanopyridine
halogen
Prior art date
1965-03-24
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
GB12886/66A
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.)

Boehringer Ingelheim Pharma GmbH and Co KG

Original Assignee
Dr Karl Thomae GmbH
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.)
1965-03-24
Filing date
1966-03-23
Publication date
1967-06-01

1966-03-23
Application filed by Dr Karl Thomae GmbH
filed
Critical
Dr Karl Thomae GmbH

1967-06-01
Publication of GB1070308A
publication
Critical
patent/GB1070308A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

Classifications

A—HUMAN NECESSITIES

A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE

A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES

A61K31/00—Medicinal preparations containing organic active ingredients

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

C07D401/04—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 directly linked by a ring-member-to-ring-member bond

Abstract

Novel compounds of the formula wherein the 1-position of the isoquinoline ring is attached to the 3- or 4-position of the pyridine ring, and R1 is C1- 5 alkyl or benzyl, optionally substituted by halogen or CH3; R2 is C1- 5 alkyl or R1 and R2 together with the 3 carbon of the isoquinoline represent a 5-6-membered spirocyclic alkane ring; R3 is H, halogen or C1- 3 alkyl; R4 and R5 are H or C1- 3 alkyl, may be prepared by one of the following four methods, wherein R1-R5 are as defined above: -(a) by cyclization, with elimination of water, of a compound of formula (b) by reacting a metal halide complex of a 4-cyanopyridine of formula with a compound of formula wherein one of X and Y is H and the other is halogen or OH, which may be esterified with a carboxylic or sulphonic acid; (c) by reacting a 4-cyanopyridine of the formula given above with a styrene of formula in the presence of a Lewis acid; or (d) by reacting a 4-cyanopyridine as aforementioned with a compound of formula wherein A and B are defined as for X and Y above, or together A and B represent a direct C-C bond, at elevated temperature in the presence of a cyclization agent. 2 – Chloro – 2 – methyl – 1 – phenyl propane is prepared by chlorination, e.g. with HCl, of dimethyl benzyl carbinol. A pharmaceutical composition comprises a compound of the first formula given above, or a non-toxic salt thereof, together with a pharmaceutical carrier. The composition has antiphlogistic, antipyretic, analgesic, spasmolytic or sedative properties, and suitably takes any conventional form for oral, parental or rectal administration.

GB12886/66A
1965-03-24
1966-03-23
Pyridyl dihydroisoquinolines

Expired

GB1070308A
(en)

Applications Claiming Priority (4)

Application Number
Priority Date
Filing Date
Title

DET0028238

1965-03-24

DET0029988

1965-12-10

DET0030096

1965-12-22

DET0031921

1966-08-26

Publications (1)

Publication Number
Publication Date

GB1070308A
true

GB1070308A
(en)

1967-06-01

Family
ID=38089161
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB12886/66A
Expired

GB1070308A
(en)

1965-03-24
1966-03-23
Pyridyl dihydroisoquinolines

Country Status (11)

Country
Link

US
(1)

US3457265A
(en)

BE
(1)

BE688799A
(en)

CH
(2)

CH471787A
(en)

DE
(1)

DE1620496A1
(en)

DK
(2)

DK116587B
(en)

ES
(1)

ES344387A1
(en)

FR
(1)

FR5269M
(en)

GB
(1)

GB1070308A
(en)

IL
(1)

IL26700A
(en)

NL
(1)

NL6615253A
(en)

SE
(2)

SE311359B
(en)

Cited By (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US5118690A
(en)

*

1989-09-20
1992-06-02
John Wyeth & Brother Limited
Pharmaceutical tetrahydroisoquinolines

Families Citing this family (5)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

DE1620549A1
(en)

*

1966-06-16
1970-08-20
Thomae Gmbh Dr K

Process for the preparation of new pyridyl-tetrahydroisoquinolines

US3517015A
(en)

*

1969-03-10
1970-06-23
Sandoz Ag
Tetrahydro-isoquino(2,1-d)(1,4)benzodiazepines

DE2811361A1
(en)

*

1978-03-16
1979-09-27
Hoechst Ag

NEW ISOCHINOLINALDEHYDE AND THE METHOD OF MANUFACTURING IT

DE3143876A1
(en)

*

1981-11-05
1983-05-11
Boehringer Ingelheim KG, 6507 Ingelheim

NEUE1-FURYL-3,4-DIHYDROISOCHINOLINE, MEDICINAL PRODUCTS CONTAINING IT, AND METHOD FOR THE PRODUCTION AND USE THEREOF

DE3244594A1
(en)

*

1982-12-02
1984-06-07
Hoechst Ag, 6230 Frankfurt

1-PHENYLISOCHINOLINE DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF, PHARMACEUTICAL PREPARATIONS CONTAINING THIS COMPOUND AND THE USE THEREOF

Family Cites Families (3)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US3133926A
(en)

*

1961-05-23
1964-05-19
Ciba Geigy Corp
1-(pyridyl-lower alkyl)-1, 2, 3, 4-tetrahydro-isoquinolines

GB973911A
(en)

*

1962-06-04
1964-11-04
Ici Ltd
Dihydroisoquinoline derivatives

US3301857A
(en)

*

1963-08-26
1967-01-31
Hoffmann La Roche
Spiro

1965

1965-03-24
DE
DE19651620496
patent/DE1620496A1/en
active
Pending

1966

1966-03-02
US
US531042A
patent/US3457265A/en
not_active
Expired – Lifetime

1966-03-17
CH
CH385166A
patent/CH471787A/en
not_active
IP Right Cessation

1966-03-22
SE
SE3793/66A
patent/SE311359B/xx
unknown

1966-03-23
DK
DK150866AA
patent/DK116587B/en
unknown

1966-03-23
GB
GB12886/66A
patent/GB1070308A/en
not_active
Expired

1966-03-24
FR
FR54887A
patent/FR5269M/fr
not_active
Expired

1966-10-16
IL
IL26700A
patent/IL26700A/en
unknown

1966-10-24
BE
BE688799D
patent/BE688799A/xx
unknown

1966-10-28
NL
NL6615253A
patent/NL6615253A/xx
unknown

1967

1967-07-14
CH
CH1007867A
patent/CH536309A/en
not_active
IP Right Cessation

1967-08-23
ES
ES344387A
patent/ES344387A1/en
not_active
Expired

1967-08-24
SE
SE11862/67A
patent/SE328885B/xx
unknown

1967-08-25
DK
DK431267AA
patent/DK123413B/en
unknown

Cited By (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US5118690A
(en)

*

1989-09-20
1992-06-02
John Wyeth & Brother Limited
Pharmaceutical tetrahydroisoquinolines

Also Published As

Publication number
Publication date

CH536309A
(en)

1973-04-30

SE311359B
(en)

1969-06-09

CH471787A
(en)

1969-04-30

IL26700A
(en)

1970-11-30

SE328885B
(en)

1970-09-28

NL6615253A
(en)

1967-06-12

US3457265A
(en)

1969-07-22

DK123413B
(en)

1972-06-19

DE1620496A1
(en)

1970-01-02

DK116587B
(en)

1970-01-26

BE688799A
(en)

1967-03-31

ES344387A1
(en)

1968-12-01

FR5269M
(en)

1967-07-31

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