GB1506200A

GB1506200A – Glycosides
– Google Patents

GB1506200A – Glycosides
– Google Patents
Glycosides

Info

Publication number
GB1506200A

GB1506200A
GB18098/75A
GB1809875A
GB1506200A
GB 1506200 A
GB1506200 A
GB 1506200A
GB 18098/75 A
GB18098/75 A
GB 18098/75A
GB 1809875 A
GB1809875 A
GB 1809875A
GB 1506200 A
GB1506200 A
GB 1506200A
Authority
GB
United Kingdom
Prior art keywords
resulting
nitrobenzoyl
derivative
reacting
chloride
Prior art date
1975-04-30
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
GB18098/75A
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.)

Pfizer Italia SRL

Original Assignee
Farmaceutici Italia SpA
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.)
1975-04-30
Filing date
1975-04-30
Publication date
1978-04-05

1975-04-30
Application filed by Farmaceutici Italia SpA
filed
Critical
Farmaceutici Italia SpA

1975-04-30
Priority to GB18098/75A
priority
Critical
patent/GB1506200A/en

1976-04-09
Priority to US05/675,696
priority
patent/US4112076A/en

1976-04-15
Priority to NLAANVRAGE7604049,A
priority
patent/NL179587C/en

1976-04-26
Priority to AT302676A
priority
patent/AT345457B/en

1976-04-26
Priority to SU762353457A
priority
patent/SU728719A3/en

1976-04-27
Priority to AU13390/76A
priority
patent/AU500439B2/en

1976-04-28
Priority to JP51049308A
priority
patent/JPS51133262A/en

1976-04-28
Priority to SE7604908A
priority
patent/SE431875B/en

1976-04-28
Priority to ZA762562A
priority
patent/ZA762562B/en

1976-04-28
Priority to DK189676A
priority
patent/DK150203C/en

1976-04-29
Priority to ES447433A
priority
patent/ES447433A1/en

1976-04-29
Priority to BE166557A
priority
patent/BE841266A/en

1976-04-29
Priority to CH541176A
priority
patent/CH541176A4/xx

1976-04-29
Priority to DE2618822A
priority
patent/DE2618822C3/en

1976-04-29
Priority to FR7612701A
priority
patent/FR2309234A1/en

1976-04-30
Priority to CA251,514A
priority
patent/CA1061335A/en

1978-04-05
Publication of GB1506200A
publication
Critical
patent/GB1506200A/en

1980-02-29
Priority to SE8001615A
priority
patent/SE436884B/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

Classifications

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS

C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals

C07H15/20—Carbocyclic rings

C07H15/24—Condensed ring systems having three or more rings

C07H15/252—Naphthacene radicals, e.g. daunomycins, adriamycins

A—HUMAN NECESSITIES

A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE

A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

A61P35/00—Antineoplastic agents

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS

C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium

C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen

C07H5/06—Aminosugars

G—PHYSICS

G04—HOROLOGY

G04B—MECHANICALLY-DRIVEN CLOCKS OR WATCHES; MECHANICAL PARTS OF CLOCKS OR WATCHES IN GENERAL; TIME PIECES USING THE POSITION OF THE SUN, MOON OR STARS

G04B37/00—Cases

G04B37/0008—Cases for pocket watches and wrist watches

G04B37/0025—Cases for pocket watches and wrist watches with cover or bottom with a spring (savonette) bench watches opening or closing with spring action G04B37/0463

Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE

Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

Y02P20/00—Technologies relating to chemical industry

Y02P20/50—Improvements relating to the production of bulk chemicals

Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

1506200 Daunomycin and adriamycin derivatives SOC FARMACEUTICI ITALIA SpA 21 April 1976 [30 April 1975] 18098/75 Heading C2C Daunomycin and the 41-epi derivatives and the novel 31,41-epi, 31,41-epi-61-hydroxy and 4 – demethoxy – 41 – epi derivatives of daunomycin and adriamycin (in α-anomer form) are prepared by reacting daunomycinone or its 4- demethoxy derivative with the appropriate N 1 O- protected 1-halo-daunosamine in an organic solvent in the presence of a soluble silver salt catalyst and a molecular sieve as dehydrating agent, removing the protecting groups and, if necessary, brominating or iodinating the resulting daunomycin or derivative thereof and hydrolysing the resulting 14-bromo or -iodo derivative with an alkali metal formate to form the corresponding adriamycin. 2,3 – Dideoxy – 4,6 – di – O – p – nitrobenzoyl – 3- N – trifluoro – acetyl – α – L – ribo – hexopyranosyl chloride is prepared by reacting 4,6-O- benzylidene – 2 – deoxy – α – L – erythro – hexopyranosoid-3-ulose with methanolic hydroxylamine, reducing the resulting oxime with LiAlH 4 , treating the resulting amine with methanolic HCl and then trifluoroacetic anhydride, reacting the resulting methyl 2,3- dideoxy – 3 – N – trifluoroacetyl – α – L – ribohexapyranoside with p-nitrobenzoyl chloride, treating the resulting di-p-nitrobenzoate with HCl, reacting the resulting pyranose with p-nitrobenzoyl chloride and chlorinating the resulting tri-O-p-nitrobenzoyl derivative. 2,3,6 – Trideoxy – 3 – N – trifluoroacetyl – 4- O – p – nitro – benzoyl – α – L@- ribo – hexopyranosyl chloride is prepared by brominating methyl 2,3 – dideoxy – 3 – N – trifluoroacetyl – α – L- ribopyranoside with N-bromosuccinimide, reducing the resulting 6-bromo derivative with Pd-C, treating the resulting methyl 2,3,6- trideoxy – 3 – trifluoroacetamido – α – L – ribohexopyranoside with p-nitrobenzoyl chloride, treating the resulting 4-O-p-nitrobenzoyl derivawith HCl, reacting the resulting pyranose with p-nitrobenzoyl chloride and chlorinating the resulting di-p-nitrobenzoyl derivative with HCl.

GB18098/75A
1975-04-30
1975-04-30
Glycosides

Expired

GB1506200A
(en)

Priority Applications (17)

Application Number
Priority Date
Filing Date
Title

GB18098/75A

GB1506200A
(en)

1975-04-30
1975-04-30
Glycosides

US05/675,696

US4112076A
(en)

1975-04-30
1976-04-09
Epi-daunomycin and epi-adriamycin compounds and method of use

NLAANVRAGE7604049,A

NL179587C
(en)

1975-04-30
1976-04-15

METHOD FOR PREPARING DAUNOMYCIN COMPOUNDS, AND ANTI-CANCER MEDICINAL PROPERTIES WITH THESE COMPOSITIONS THEREIN

AT302676A

AT345457B
(en)

1975-04-30
1976-04-26

METHOD FOR PRODUCING NEW GLYCOSIDE COMPOUNDS

SU762353457A

SU728719A3
(en)

1975-04-30
1976-04-26
Method of preparing anthracycline glycosides

AU13390/76A

AU500439B2
(en)

1975-04-30
1976-04-27
Anthracycline glycosides

DK189676A

DK150203C
(en)

1975-04-30
1976-04-28

PROCEDURE FOR PREPARING ALFA ANOMERS OF ANTHRACYCLING LYCOSIDES OR HYDROCHLORIDES THEREOF

SE7604908A

SE431875B
(en)

1975-04-30
1976-04-28

PROCEDURE FOR THE PREPARATION OF DAUNOMYCINE DERIVATIVES

ZA762562A

ZA762562B
(en)

1975-04-30
1976-04-28
Glycosides

JP51049308A

JPS51133262A
(en)

1975-04-30
1976-04-28
Antiitumor glycoside and preparation thereof

ES447433A

ES447433A1
(en)

1975-04-30
1976-04-29
Epi-daunomycin and epi-adriamycin compounds and method of use

BE166557A

BE841266A
(en)

1975-04-30
1976-04-29

ANTITUMOR GLUCOSIDES AND THEIR PREPARATION PROCESS

CH541176A

CH541176A4
(en)

1975-04-30
1976-04-29

DE2618822A

DE2618822C3
(en)

1975-04-30
1976-04-29

Anthracycline glycosides and processes for their preparation

FR7612701A

FR2309234A1
(en)

1975-04-30
1976-04-29

ANTITUMOR GLUCOSIDES AND THEIR PREPARATION PROCESS

CA251,514A

CA1061335A
(en)

1975-04-30
1976-04-30
Process for the preparation of antitumor glycosides

SE8001615A

SE436884B
(en)

1975-04-30
1980-02-29

PROCEDURE FOR PREPARING ADRIAMYCINE DERIVATIVES

Applications Claiming Priority (1)

Application Number
Priority Date
Filing Date
Title

GB18098/75A

GB1506200A
(en)

1975-04-30
1975-04-30
Glycosides

Publications (1)

Publication Number
Publication Date

GB1506200A
true

GB1506200A
(en)

1978-04-05

Family
ID=10106621
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB18098/75A
Expired

GB1506200A
(en)

1975-04-30
1975-04-30
Glycosides

Country Status (16)

Country
Link

US
(1)

US4112076A
(en)

JP
(1)

JPS51133262A
(en)

AT
(1)

AT345457B
(en)

AU
(1)

AU500439B2
(en)

BE
(1)

BE841266A
(en)

CA
(1)

CA1061335A
(en)

CH
(1)

CH541176A4
(en)

DE
(1)

DE2618822C3
(en)

DK
(1)

DK150203C
(en)

ES
(1)

ES447433A1
(en)

FR
(1)

FR2309234A1
(en)

GB
(1)

GB1506200A
(en)

NL
(1)

NL179587C
(en)

SE
(2)

SE431875B
(en)

SU
(1)

SU728719A3
(en)

ZA
(1)

ZA762562B
(en)

Families Citing this family (30)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

FR2374333A1
(en)

*

1976-12-20
1978-07-13
Inst Int Pathologie Cellulaire
Antitumoural (N)-acyl daunorubicin or adriamycin derivs. – e.g. (N)-citraconyl daunorubicin, prepd. by acylation with corresp. acid anhydride

GB1550879A
(en)

*

1976-12-22
1979-08-22
Farmaceutici Italia
Antitumour glycosides

GB1567392A
(en)

*

1977-02-22
1980-05-14
Farmaceutici Italia
Daunorubicin derivatives

US4201773A
(en)

*

1978-07-26
1980-05-06
The United States Of America As Represented By The Department Of Health, Education And Welfare
7-O-(2,6-Dideoxy-α-L-lyxo-hexopyranosyl)-daunomycinone, desmethoxy daunomycinone, adriamycinone, and carminomycinone

IT1196402B
(en)

*

1978-11-21
1988-11-16
Erba Farmitalia

ANTI-TUMORAL ANTIBIOTICS

NL8001417A
(en)

*

1979-03-17
1980-09-19
Erba Farmitalia

ANTITUMORGLYCOSIDES.

JPS5673039A
(en)

*

1979-08-20
1981-06-17
Hoffmann La Roche
Naphthacene derivative

EP0024727B1
(en)

*

1979-09-01
1982-05-26
FARMITALIA CARLO ERBA S.p.A.
Anthracycline glycosides, processes for their preparation and pharmaceutical composition containing them

US4345068A
(en)

*

1979-11-22
1982-08-17
Farmitalia Carlo Erba S.P.A.
Process for the preparation of 4′-epidaunorubicin, 3′,4′-diepidaunorubicin, their doxorubicin analogs, and intermediates used in said process

US4301276A
(en)

*

1980-03-07
1981-11-17
Purdue University
Synthesis of daunosamine hydrochloride and intermediates used in its preparation

US4298726A
(en)

*

1980-03-07
1981-11-03
Purdue University
Synthesis of N-benzoyl-L-ristosamine and intermediates used in its preparation

US4345070A
(en)

*

1980-09-29
1982-08-17
Farmitalia Carlo Erba S.P.A.
Process for the preparation of 4′-deoxy-daunorubicin and 4′-deoxy-doxorubicin

US5138042A
(en)

*

1981-05-28
1992-08-11
Farmitalia Carlo Erba S.P.A.
6-deoxyanthracyclines

NZ201899A
(en)

*

1981-09-18
1985-09-13
Erba Farmitalia
Anthracycline glycosides and pharmaceutical compositions

GB8426672D0
(en)

*

1984-10-22
1984-11-28
Erba Farmitalia
Pharmaceutical compositions

GB2196626B
(en)

*

1986-10-15
1990-09-19
Erba Farmitalia
Antitumor anthracycline glycosides, their preparation, intermediates thereof, and compositions and use therefor

DE3641835A1
(en)

*

1986-12-08
1988-06-16
Behringwerke Ag

CYTOSTATICALLY EFFECTIVE ANTHRACYCLINE DERIVATIVES

GB8803076D0
(en)

*

1988-02-10
1988-03-09
Erba Carlo Spa
3′-deamino-4′-deoxy-4′-amino anthracyclines

GB9216962D0
(en)

*

1992-08-11
1992-09-23
Erba Carlo Spa
Therapeutically active naphthalenesulfonic-pyrrolecarboxamido derivatives

RU2341530C2
(en)

*

2003-07-02
2008-12-20
Солакс Корпорейшн
Thermostable crystal epirubicine hydrochloride and method of production thereof

US20090099346A1
(en)

*

2003-07-02
2009-04-16
Victor Matvienko
Thermally stable crystalline epirubicin hydrochloride

US7388083B2
(en)

*

2005-03-07
2008-06-17
Solux Corporation
Epimerization of 4′-C bond and modification of 14-CH3-(CO)-fragment in anthracyclin antibiotics

CN101331147B
(en)

*

2005-12-13
2011-11-30
苏洛克股份有限公司
Method for preparing 4-demethyldaunorubicin

US8802830B2
(en)

*

2005-12-20
2014-08-12
Solux Corporation
Synthesis of epirubicin from 13-dihydrodaunorubicine

US8357785B2
(en)

*

2008-01-08
2013-01-22
Solux Corporation
Method of aralkylation of 4′-hydroxyl group of anthracylins

EP2301943B1
(en)

*

2009-09-08
2014-01-08
Heraeus Precious Metals GmbH & Co. KG
Crystallization of epidaunorubicin x HCI

DE102011103751A1
(en)

2011-05-31
2012-12-06
Heraeus Precious Metals Gmbh & Co. Kg

Crystallization of epirubicin hydrochloride

DE102011111991A1
(en)

*

2011-08-30
2013-02-28
Lead Discovery Center Gmbh

New cyclosporin derivatives

CN103204888B
(en)

*

2012-01-15
2016-08-17
山东新时代药业有限公司
A kind of preparation method of intermediate of epirubicin hydrochloride

US10301343B2
(en)

2015-03-30
2019-05-28
Meiji Seika Pharma Co., Ltd.
Method of producing epirubicin and novel production intermediate thereof

Family Cites Families (3)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US3803124A
(en)

*

1968-04-12
1974-04-09
Farmaceutici It Soc
Process for the preparation of adriamycin and adriamycinone and adriamycin derivatives

GB1467383A
(en)

*

1974-06-12
1977-03-16
Farmaceutici Italia
Daunomycin analogues

GB1470860A
(en)

*

1974-10-29
1977-04-21
Farmaceutici Italia
Anthracycline glycosides

1975

1975-04-30
GB
GB18098/75A
patent/GB1506200A/en
not_active
Expired

1976

1976-04-09
US
US05/675,696
patent/US4112076A/en
not_active
Expired – Lifetime

1976-04-15
NL
NLAANVRAGE7604049,A
patent/NL179587C/en
not_active
IP Right Cessation

1976-04-26
AT
AT302676A
patent/AT345457B/en
not_active
IP Right Cessation

1976-04-26
SU
SU762353457A
patent/SU728719A3/en
active

1976-04-27
AU
AU13390/76A
patent/AU500439B2/en
not_active
Expired

1976-04-28
ZA
ZA762562A
patent/ZA762562B/en
unknown

1976-04-28
SE
SE7604908A
patent/SE431875B/en
not_active
IP Right Cessation

1976-04-28
JP
JP51049308A
patent/JPS51133262A/en
active
Granted

1976-04-28
DK
DK189676A
patent/DK150203C/en
not_active
IP Right Cessation

1976-04-29
ES
ES447433A
patent/ES447433A1/en
not_active
Expired

1976-04-29
BE
BE166557A
patent/BE841266A/en
not_active
IP Right Cessation

1976-04-29
CH
CH541176A
patent/CH541176A4/xx
not_active
IP Right Cessation

1976-04-29
FR
FR7612701A
patent/FR2309234A1/en
active
Granted

1976-04-29
DE
DE2618822A
patent/DE2618822C3/en
not_active
Expired

1976-04-30
CA
CA251,514A
patent/CA1061335A/en
not_active
Expired

1980

1980-02-29
SE
SE8001615A
patent/SE436884B/en
not_active
IP Right Cessation

Also Published As

Publication number
Publication date

ES447433A1
(en)

1977-07-01

US4112076A
(en)

1978-09-05

CH624125A
(en)

1981-07-15

SE7604908L
(en)

1976-10-31

SE8001615L
(en)

1980-02-29

DE2618822A1
(en)

1976-11-11

NL7604049A
(en)

1976-11-02

DE2618822C3
(en)

1983-04-28

DE2618822B2
(en)

1982-09-16

CA1061335A
(en)

1979-08-28

AU1339076A
(en)

1977-11-03

AU500439B2
(en)

1979-05-24

AT345457B
(en)

1978-09-25

NL179587B
(en)

1986-05-01

SE436884B
(en)

1985-01-28

NL179587C
(en)

1986-10-01

SU728719A3
(en)

1980-04-15

DK150203B
(en)

1987-01-05

CH541176A4
(en)

1981-07-15

BE841266A
(en)

1976-10-29

SE431875B
(en)

1984-03-05

DK189676A
(en)

1976-10-31

DK150203C
(en)

1987-11-02

FR2309234A1
(en)

1976-11-26

ZA762562B
(en)

1977-04-27

JPS5619878B2
(en)

1981-05-09

ATA302676A
(en)

1978-01-15

JPS51133262A
(en)

1976-11-18

FR2309234B1
(en)

1978-08-25

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Legal Events

Date
Code
Title
Description

1978-08-16
PS
Patent sealed [section 19, patents act 1949]

1988-08-10
732
Registration of transactions, instruments or events in the register (sect. 32/1977)

1996-05-22
PE20
Patent expired after termination of 20 years

Effective date:
19960420

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