GB1363674A

GB1363674A – Cardenolide derivatives and a process for their manufacture
– Google Patents

GB1363674A – Cardenolide derivatives and a process for their manufacture
– Google Patents
Cardenolide derivatives and a process for their manufacture

Info

Publication number
GB1363674A

GB1363674A
GB4996571A
GB4996571A
GB1363674A
GB 1363674 A
GB1363674 A
GB 1363674A
GB 4996571 A
GB4996571 A
GB 4996571A
GB 4996571 A
GB4996571 A
GB 4996571A
GB 1363674 A
GB1363674 A
GB 1363674A
Authority
GB
United Kingdom
Prior art keywords
compounds
give
amino
oct
free
Prior art date
1970-10-29
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
GB4996571A
Inventor
U Stache
W Fritsch
W Haide
K Radscheit
Lindner
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.)

Hoechst AG

Original Assignee
Hoechst AG
Farbwerke Hoechst 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.)
1970-10-29
Filing date
1971-10-27
Publication date
1974-08-14

1971-10-27
Application filed by Hoechst AG, Farbwerke Hoechst AG
filed
Critical
Hoechst AG

1974-08-14
Publication of GB1363674A
publication
Critical
patent/GB1363674A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

150000001738
cardenolides
Chemical class

0.000
title
1

238000004519
manufacturing process
Methods

0.000
title
1

238000000034
method
Methods

0.000
title
1

150000001875
compounds
Chemical class

0.000
abstract
4

125000002887
hydroxy group
Chemical group

[H]O*

0.000
abstract
2

150000003839
salts
Chemical class

0.000
abstract
2

RXUHKPOBBNOXCX-YQGQCKGGSA-N
3-[(8R,9S,10S,13S,14R,17S)-3-amino-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Chemical class

NC1CC2CC[C@@H]3[C@H](CC[C@@]4(C)[C@@H]3CC[C@@H]4C=3COC(=O)C=3)[C@]2(CC1)C
RXUHKPOBBNOXCX-YQGQCKGGSA-N
0.000
abstract
1

AVXURJPOCDRRFD-UHFFFAOYSA-N
Hydroxylamine
Chemical compound

ON
AVXURJPOCDRRFD-UHFFFAOYSA-N
0.000
abstract
1

HCHKCACWOHOZIP-UHFFFAOYSA-N
Zinc
Chemical compound

[Zn]
HCHKCACWOHOZIP-UHFFFAOYSA-N
0.000
abstract
1

150000007933
aliphatic carboxylic acids
Chemical class

0.000
abstract
1

230000003177
cardiotonic effect
Effects

0.000
abstract
1

239000000969
carrier
Substances

0.000
abstract
1

239000003795
chemical substances by application
Substances

0.000
abstract
1

239000000203
mixture
Substances

0.000
abstract
1

238000007911
parenteral administration
Methods

0.000
abstract
1

239000008194
pharmaceutical composition
Substances

0.000
abstract
1

239000011701
zinc
Substances

0.000
abstract
1

229910052725
zinc
Inorganic materials

0.000
abstract
1

Classifications

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07J—STEROIDS

C07J19/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 by a lactone ring

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07J—STEROIDS

C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring

C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton

Abstract

1363674 3-Aminocardenolides FARBWERKE HOECHST AG 27 Oct 1971 [29 Oct 1970] 49965/71 Heading C2U The invention comprises compounds of formula wherein R 1 is H or C 1-4 aliphatic carboxylic acyl; R 2 and R 3 are each H or OH, or R 2 and R 3 together represent an α- or #-epoxy group or #14-unsaturation; R 4 , R 5 and R 7 are each H or free or esterified hydroxyl; R 6 is H or free, esterified or etherified hydroxyl; and R 8 is H or OH; and salts of those compounds wherein R 1 is H. Compounds I are prepared from the corresponding 3-ones (which may also contain a 19- oxo group) by reaction with hydroxylamine or a salt thereof to give a 3-oxime which is reduced using zinc in the presence of an aliphatic carboxylic acid to give a 3-amino and/or 3-acylamino compound I. The 3-acylamino compounds (and mixtures thereof with the 3-amino compounds) may be hydrolysed to give the 3- amino compounds and the latter may be salified or acylated. The inventive compounds are said to be cardiotonic, and may be made up with carriers into pharmaceutical compositions for oral and parenteral administration.

GB4996571A
1970-10-29
1971-10-27
Cardenolide derivatives and a process for their manufacture

Expired

GB1363674A
(en)

Applications Claiming Priority (1)

Application Number
Priority Date
Filing Date
Title

DE2053117A

DE2053117C3
(en)

1970-10-29
1970-10-29

3-amine-4,5-dehydrocardenolide, process for their preparation and their use

Publications (1)

Publication Number
Publication Date

GB1363674A
true

GB1363674A
(en)

1974-08-14

Family
ID=5786520
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB4996571A
Expired

GB1363674A
(en)

1970-10-29
1971-10-27
Cardenolide derivatives and a process for their manufacture

Country Status (14)

Country
Link

US
(1)

US3801570A
(en)

AT
(1)

AT311572B
(en)

AU
(1)

AU464564B2
(en)

BE
(1)

BE774627A
(en)

CA
(1)

CA951720A
(en)

CH
(1)

CH572069A5
(en)

DE
(1)

DE2053117C3
(en)

DK
(1)

DK128739B
(en)

ES
(1)

ES396266A1
(en)

FR
(1)

FR2111927B1
(en)

GB
(1)

GB1363674A
(en)

NL
(1)

NL7114570A
(en)

SE
(1)

SE377128B
(en)

ZA
(1)

ZA717199B
(en)

1970

1970-10-29
DE
DE2053117A
patent/DE2053117C3/en
not_active
Expired

1971

1971-10-22
NL
NL7114570A
patent/NL7114570A/xx
unknown

1971-10-22
ES
ES396266A
patent/ES396266A1/en
not_active
Expired

1971-10-25
CA
CA125,927,A
patent/CA951720A/en
not_active
Expired

1971-10-26
CH
CH1559971A
patent/CH572069A5/xx
not_active
IP Right Cessation

1971-10-27
AU
AU35037/71A
patent/AU464564B2/en
not_active
Expired

1971-10-27
US
US00193163A
patent/US3801570A/en
not_active
Expired – Lifetime

1971-10-27
GB
GB4996571A
patent/GB1363674A/en
not_active
Expired

1971-10-28
DK
DK526471AA
patent/DK128739B/en
unknown

1971-10-28
ZA
ZA717199A
patent/ZA717199B/en
unknown

1971-10-28
BE
BE774627A
patent/BE774627A/en
unknown

1971-10-28
AT
AT931371A
patent/AT311572B/en
not_active
IP Right Cessation

1971-10-29
FR
FR7138994A
patent/FR2111927B1/fr
not_active
Expired

1971-10-29
SE
SE7113758A
patent/SE377128B/xx
unknown

Also Published As

Publication number
Publication date

NL7114570A
(en)

1972-05-03

DE2053117B2
(en)

1979-03-22

AT311572B
(en)

1973-11-26

FR2111927B1
(en)

1975-04-18

BE774627A
(en)

1972-04-28

FR2111927A1
(en)

1972-06-09

CH572069A5
(en)

1976-01-30

AU3503771A
(en)

1973-05-03

ES396266A1
(en)

1974-04-16

DE2053117C3
(en)

1979-11-15

CA951720A
(en)

1974-07-23

AU464564B2
(en)

1975-08-28

ZA717199B
(en)

1972-07-26

DE2053117A1
(en)

1972-06-22

US3801570A
(en)

1974-04-02

SE377128B
(en)

1975-06-23

DK128739B
(en)

1974-06-24

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(en)

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(en)

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(en)

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(en)

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(en)

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Legal Events

Date
Code
Title
Description

1974-12-27
PS
Patent sealed [section 19, patents act 1949]

1979-05-31
PCNP
Patent ceased through non-payment of renewal fee

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