(12) Translation of european patent specification

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1 (12) Translation of european patent specification (11) NO/EP B1 (19) NO NORWAY (1) Int Cl. C07H 1/22 ( ) Norwegian Industrial Property Office (21) Translation Published (80) Date of The European Patent Office Publication of the Granted Patent (86) European Application Nr (86) European Filing Date (87) The European Application s Publication Date (30) Priority , US, (84) Designated Contracting States: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR (73) Proprietor Synbias Pharma AG, Pestalozzistrasse 2, 8200 Schaffhausen, CH-Sveits (72) Inventor Zabudkin, Alexander, Universitetskaja Str. 27, Fl. 26, 830 Donetsk, UA-Ukraina Matvienko, Victor, Panfilova 20, Fl. 37, Donetsk, UA-Ukraina Matvyeyev, Alexey, Panfilova 20, Fl. 30, Donetsk, UA-Ukraina (74) Agent or Attorney Bryn Aarflot AS, Postboks 449 Sentrum, 04 OSLO, Norge (4) Title Method of producing 4-demethoxydaunorubicin (6) References Cited: US-A US-A US-B

2 Enclosed is a translation of the patent claims in Norwegian. Please note that as per the Norwegian Patents Acts, section 66i the patent will receive protection in Norway only as far as there is agreement between the translation and the language of the application/patent granted at the EPO. In matters concerning the validity of the patent, language of the application/patent granted at the EPO will be used as the basis for the decision. The patent documents published by the EPO are available through Espacenet ( or via the search engine on our website here: NO/EP218077

3 NO/EP Patentkrav 1. En metode for fremstilling av 4-demetoksydaunorubicin eller et salt derav som har den kjemiske strukturen med formel (I), hvor An- representerer et anion, omfattende: (a) omdannelse av et daunorubicin hydrokloridsalt som har den kjemiske strukturen med formel (II) til et 3'-beskyttet daunorubicin (3'-Prot-daunorubicin) som er valgt fra gruppen bestående av forbindelsene som har de kjemiske strukturene med formlene (III) og (IV), hvor omdannelsen av 3'-aminogruppesaltet til et 3'-azid ved kontakting med et azid-dannende reagens resulterer i dannelsen av (III) og omdannelse av 3'1 aminogruppesaltet til et 3'-trifluoracetmid ved kontakting med et trifluoracetylerende reagens resulterer i dannelse av (IV);

4 NO/EP (b) demetylering av 3'-Prot-daunorubicin med formel (III) eller (IV) ved kontakting med MgCl2 (vannfri) og i nærvær av Kl (vannfri) i et vannfritt løsningsmiddel, hvilket gir et 4-demetyl-3'-Prot-daunorubicin som er valgt fra gruppen bestående av forbindelsene som har de kjemiske strukturene med formlene (V) og (VI), henholdsvis, hvor demetylering av (III) resulterer i dannelsen av (V) og demetylering av (IV) resulterer i dannelse av (VI), hvor reaksjonen blir utført ved en reaksjonstemperatur i området -80 C og spesielt i området C og hvor det vannfrie løsningsmidlet er valgt fra gruppen bestående av alkaner, cykloalkaner, halogenalkaner, arener, alkyloksider, etere, C4-C6 alkoholer og karbondisulfid; 1 (c) trifluormetansulfonylering av 4-demetyl-3'-Prot-daunorubicin med formel (V) eller (VI) ved kontakting med et trifluormetansulfoneringsreagens, hvilket gir et 4-Otrifluormetansulfonyl-3'-Prot-daunorubicin som er valgt fra gruppen bestående av forbindelsene som har de kjemiske strukturene med formlene (VII) og (VIII), henholdsvis, hvor trifluormetansulfonylering av (V) resulterer i dannelsen av (VII) og trifluormetansulfonylering av (VI) resulterer i dannelsen av (VIII);

5 NO/EP (d) reduksjon av 4-O-trifluormetansulfonyl-3'-Prot-daunorubicin med formel (VII) eller (VIIII) ved kontakting med et reduksjonsmiddel, hvilket gir et 4-demetoksy-3'-Protdaunorubicin som er valgt fra gruppen bestående av forbindelsene som har de kjemiske strukturene med formlene (IX) og (X), henholdsvis, hvor reduksjonen av (VII) resulterer i dannelsen av (IX) og reduksjon av (VIII) resulterer i dannelsen av (X); og 1 (e) fjerning av den beskyttende 3'-Prot gruppen fra 4-demetoksy-3'-Protdaunorubicin valgt fra gruppen bestående av forbindelsen med formel (IX) og forbindelsen med formel (X), hvor forbindelsen med formel (IX) blir bragt i kontakt med et azid-reduserende reagens eller forbindelsen med formel (X) blir bragt i kontakt med en alkalisk løsning, med resulterende dannelse av en 3'-aminogruppe, hvilket gir 4-demetoksy-daunorubicin og, eventuelt, kontakting av 4-demetoksydaunorubicin med en syre med formel H + An -, hvilket gir 4-demetoksydaunorubicinsaltet med formel (I) Metode ifølge krav 1, hvor trinn (a) blir utført ved omsetning av daunorubicin hydroklorid med en forbindelse som er valgt fra gruppen bestående av trifluormetansulfonyl azid og trifluoreddiksyreanhydrid for å gi en forbindelse med formel (III) eller en forbindelse med formel (IV), henholdsvis Metode ifølge krav 1, hvor trinn (c) blir utført ved omsetning av 4-demetyl-3'-Protdaunorubicin med formel (V) eller (VI) med trifluormetansulfonsyreanhydrid for å gi trifluormetansulfonaerte forbindelser med formel (VII) eller (VIII), henholdsvis og hvor trinn (c) blir fortrinnsvis utført i pyridin i nærvær av tertiære aminer Metode ifølge krav 1, hvor trinn (d) blir utført ved omsetning av 4- trifluormetansulfonyl-3'-prot-daunorubicin med formel (VII) eller (VIII) med et reduksjonsmiddel i nærvær av katalytiske mengder av forbindelser som har den generelle formel PdLnL'm, hvor

6 NO/EP L og L' uavhengig er valgt fra gruppen bestående av fosfiter og fosfiner; og n og m kan uavhengig variere fra 0 til 4; og hvor reduksjonsmidlet er valgt fra gruppen bestående av maursyre og salter av maursyre; for å gi forbindelsen med formel (IX) eller formel (X), henholdsvis.. Metode ifølge krav 4, hvor trinn (d) blir utført ved en reaksjonstemperatur i området 30-0 C i et polart aprotisk løsningsmiddel. 6. Metode ifølge krav 1, hvor azid-reduserende reagens i trinn (e) omfatter trifenylfosfin. 7. Metode ifølge krav 1, hvor den alkaliske løsningen i trinn (e) omfatter vandig natriumhydroksid Metode ifølge krav 1, som videre omfatter: isolering av 4-demetyl-3'-Protdaunorubicin med formel (V) eller (VI) oppnådd i trinn (b) ved behandling med sterke syrer ved en ph på 2, ± 1,0 og påfølgende ekstraksjon En metode for å produsere carminomycin fra et daunorubicin salt, omfattende å utføre trinn (a) og (b) ifølge krav 1 for å gi en forbindelse med formel (V) eller (VI), deretter fjerning av 3'-beskyttelsesgruppen som definert i trinn (e) i krav 1 for å gi carminomycin eller et salt derav. 2. Metode ifølge krav 9, hvor trinn (a) blir utført ved omsetning av daunorubicin hydroklorid med en forbindelse som er valgt fra gruppen bestående av trifluormetansulfonyl azid og trifluoreddiksyreanhydrid Metode ifølge krav 9, som videre omfatter: isolering av 4-demetyl-3'-Protdaunorubicin med formel (V) eller (VI) oppnådd i trinn (b) ved behandling med sterke syrer ved en ph på 2, ± 1,0 og påfølgende ekstraksjon.

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