FI84075C - Förfarande för framställning av nya antracykliner - Google Patents
Förfarande för framställning av nya antracykliner Download PDFInfo
- Publication number
- FI84075C FI84075C FI872571A FI872571A FI84075C FI 84075 C FI84075 C FI 84075C FI 872571 A FI872571 A FI 872571A FI 872571 A FI872571 A FI 872571A FI 84075 C FI84075 C FI 84075C
- Authority
- FI
- Finland
- Prior art keywords
- epi
- formula
- daunorubicin
- process according
- deoxy
- Prior art date
Links
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Claims (6)
1. Förfarande för framställning av antracyklinglykosider med den allmänna formeln II
0 OH (o i i»> r * CH.,0 0 OH l OH (II) i vilken formel R1 betecknar en väteatom eller en hydro-xylgrupp, och farmaceutiskt godtagbara syraadditionssalter därav, kännetecknat därav, att man a) omsätter 3'-amino-3'-epi-daunorubicin, upplöst i en blandning av vatten och aceton, med salicylaldehyd, b) omsätter det sä erhällna motsvarande 3'-epi-N-salicyli-denderivatet med trifluormetan-sulfonsyraanhydrid i vatten-fri diklormetan och i närvaro av torr pyridin, c) utför syrahydrolys av salicylidenskyddsgruppen vid rums-temperatur med p-toluensulfonsyra pä det sä erhällna 3'-epi-N-salicyliden-4'-O-trifluormetansulfonatet, upplöst i metanol, d) omvandlar sä erhällen 3'-deamino-4'-deoxi-3'-epi-4'-epi-3',4'-epi-imino-daunorubicin genom att behandla med tri- fluorättiksyraanhydrid, e) omsätter det sä erhällna motsvarande N-trifluoracetyl-derivatet med en katalytisk mängd av svavelsyra, 15 84075 f) utför en mild alkalisk hydrolys av N-skyddsgruppen vid 0 °C pä sä erhällen 4'-deoxi-4-epi-N-trifluoracetyl-31-de-amino-3'-hydroxi-daunorubicin.
2. Förfarande enligt patentkravet 1, känneteck-n a t därav, att den erhällna föreningen med formeln II, 1 vilken Rx betecknar en väteatom, vidarebehandlas med metanoliskt klorväte och produkten isoleras säsom motsva-rande hydroklorid.
3. Förfarande enligt patentkravet 2, känneteck- n a t därav, att den erhällna hydrokloriden omvandlas tili ett 14-bromderivat genom att omsätta den med en bromlös-ning, och det erhällna 14-bromderivatet hydrolyseras genom att använda en vattenlösning av natriumformiat.
4. Förfarande enligt patentkravet 3, känneteck-n a t därav, att en förening med formeln II, i vilken Sr en hydroxylgrupp, erhälls säsom en fri bas.
5. Förfarande enligt patentkravet 4, känneteck-n a t därav, att man vidare utför ett steg, i vilket den erhällna basen omvandlas tili den motsvarande hydrokloriden.
6. 31-deamino-4'-deoxi-3'-epi-4'-epi-3',4'-epi-imino-dau-norubicin.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB868614323A GB8614323D0 (en) | 1986-06-12 | 1986-06-12 | Anthracyclines |
| GB8614323 | 1986-06-12 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI872571A0 FI872571A0 (fi) | 1987-06-09 |
| FI872571A FI872571A (fi) | 1987-12-13 |
| FI84075B FI84075B (fi) | 1991-06-28 |
| FI84075C true FI84075C (sv) | 1991-10-10 |
Family
ID=10599357
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI872571A FI84075C (sv) | 1986-06-12 | 1987-06-09 | Förfarande för framställning av nya antracykliner |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JP2516769B2 (sv) |
| KR (1) | KR950004897B1 (sv) |
| AT (1) | AT392793B (sv) |
| AU (1) | AU595328B2 (sv) |
| BE (1) | BE1000158A4 (sv) |
| CA (1) | CA1291122C (sv) |
| CH (1) | CH676985A5 (sv) |
| DE (1) | DE3719377C2 (sv) |
| DK (1) | DK169076B1 (sv) |
| ES (1) | ES2006488A6 (sv) |
| FI (1) | FI84075C (sv) |
| FR (1) | FR2600066B1 (sv) |
| GB (2) | GB8614323D0 (sv) |
| GR (1) | GR870909B (sv) |
| HU (1) | HU196220B (sv) |
| IE (1) | IE60412B1 (sv) |
| IL (1) | IL82820A0 (sv) |
| IT (1) | IT1215552B (sv) |
| NL (1) | NL8701349A (sv) |
| NZ (1) | NZ220604A (sv) |
| PT (1) | PT85056B (sv) |
| SE (1) | SE500732C2 (sv) |
| SU (1) | SU1590045A3 (sv) |
| ZA (1) | ZA874202B (sv) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3842836A1 (de) * | 1988-12-20 | 1990-06-21 | Behringwerke Ag | Rhodomycine mit einer modifizierten kohlenhydrat-einheit |
| GB9325417D0 (en) * | 1993-12-13 | 1994-02-16 | Erba Carlo Spa | 3'- aziridino-anthracycline derivatives |
| IT1275953B1 (it) * | 1995-03-22 | 1997-10-24 | Sicor Spa | Procedimento per la preparazione di antibiotici della classe delle antracicline |
| GB9808027D0 (en) * | 1998-04-15 | 1998-06-17 | Pharmacia & Upjohn Spa | 13-dihydro-3' aziridino anthracyclines |
| AU2343900A (en) * | 1998-11-02 | 2000-05-22 | Board Of Regents, The University Of Texas System | Methods and compositions for the manufacture of highly potent anthracycline-based antitumor agents |
| GB0114654D0 (en) * | 2001-06-15 | 2001-08-08 | Pharmacia & Upjohn Spa | Anti-tumor compound |
| CN110483871A (zh) * | 2019-08-15 | 2019-11-22 | 陈全明 | 一种抗压耐磨的hdpe双壁波纹管 |
Family Cites Families (3)
| 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 |
| DE51280T1 (de) * | 1980-11-01 | 1983-01-20 | Farmitalia Carlo Erba S.p.A., 20159 Milano | Anthracyclin-glycoside, verfahren zu ihrer herstellung, zwischenprodukte und ihre herstellung und arzneimittel. |
| GB8508079D0 (en) * | 1985-03-28 | 1985-05-01 | Erba Farmitalia | Antitumor anthracyclines |
-
1986
- 1986-06-12 GB GB868614323A patent/GB8614323D0/en active Pending
-
1987
- 1987-05-19 CH CH1952/87A patent/CH676985A5/it not_active IP Right Cessation
- 1987-06-01 ES ES878701700A patent/ES2006488A6/es not_active Expired
- 1987-06-08 NZ NZ220604A patent/NZ220604A/xx unknown
- 1987-06-08 CA CA000539119A patent/CA1291122C/en not_active Expired - Fee Related
- 1987-06-09 AT AT1449/87A patent/AT392793B/de not_active IP Right Cessation
- 1987-06-09 FI FI872571A patent/FI84075C/sv not_active IP Right Cessation
- 1987-06-09 GB GB8713443A patent/GB2195998B/en not_active Expired - Fee Related
- 1987-06-09 IT IT8720834A patent/IT1215552B/it active
- 1987-06-09 IL IL82820A patent/IL82820A0/xx not_active IP Right Cessation
- 1987-06-09 FR FR878708005A patent/FR2600066B1/fr not_active Expired - Fee Related
- 1987-06-09 PT PT85056A patent/PT85056B/pt not_active IP Right Cessation
- 1987-06-10 HU HU872657A patent/HU196220B/hu unknown
- 1987-06-10 GR GR870909A patent/GR870909B/el unknown
- 1987-06-10 NL NL8701349A patent/NL8701349A/nl not_active Application Discontinuation
- 1987-06-10 BE BE8700645A patent/BE1000158A4/fr not_active IP Right Cessation
- 1987-06-10 DE DE3719377A patent/DE3719377C2/de not_active Expired - Fee Related
- 1987-06-10 IE IE153887A patent/IE60412B1/en not_active IP Right Cessation
- 1987-06-10 SE SE8702409A patent/SE500732C2/sv unknown
- 1987-06-10 AU AU74108/87A patent/AU595328B2/en not_active Ceased
- 1987-06-11 KR KR1019870005911A patent/KR950004897B1/ko not_active IP Right Cessation
- 1987-06-11 JP JP62146162A patent/JP2516769B2/ja not_active Expired - Lifetime
- 1987-06-11 DK DK298787A patent/DK169076B1/da active
- 1987-06-11 SU SU874202740A patent/SU1590045A3/ru active
- 1987-06-11 ZA ZA874202A patent/ZA874202B/xx unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: FARMITALIA CARLO ERBA S.P.A |