HRP20170329T1 - Kristaliziranje epirubicin-hidroklorida - Google Patents
Kristaliziranje epirubicin-hidroklorida Download PDFInfo
- Publication number
- HRP20170329T1 HRP20170329T1 HRP20170329TT HRP20170329T HRP20170329T1 HR P20170329 T1 HRP20170329 T1 HR P20170329T1 HR P20170329T T HRP20170329T T HR P20170329TT HR P20170329 T HRP20170329 T HR P20170329T HR P20170329 T1 HRP20170329 T1 HR P20170329T1
- Authority
- HR
- Croatia
- Prior art keywords
- range
- mixture
- volume
- epirubicin hydrochloride
- butanol
- Prior art date
Links
- MWWSFMDVAYGXBV-FGBSZODSSA-N (7s,9s)-7-[(2r,4s,5r,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;hydron;chloride Chemical compound Cl.O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 MWWSFMDVAYGXBV-FGBSZODSSA-N 0.000 title claims 11
- 229960003265 epirubicin hydrochloride Drugs 0.000 title claims 11
- 238000002425 crystallisation Methods 0.000 title 1
- 230000008025 crystallization Effects 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 15
- 239000000203 mixture Substances 0.000 claims 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 9
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 9
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 9
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 6
- 239000007864 aqueous solution Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 239000013078 crystal Substances 0.000 claims 1
- 230000002045 lasting effect Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/68—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
- A61K47/6801—Drug-antibody or immunoglobulin conjugates defined by the pharmacologically or therapeutically active agent
- A61K47/6803—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates
- A61K47/6807—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates the drug or compound being a sugar, nucleoside, nucleotide, nucleic acid, e.g. RNA antisense
- A61K47/6809—Antibiotics, e.g. antitumor antibiotics anthracyclins, adriamycin, doxorubicin or daunomycin
-
- 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
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/56—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical directly bound to a condensed ring system having three or more carbocyclic rings, e.g. daunomycin, adriamycin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Zoology (AREA)
- Animal Behavior & Ethology (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Microbiology (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (15)
1. Postupak dobivanja kristalnog epirubicin-hidroklorida, naznačen time što obuhvaća korake
(a) osiguravanje epirubicin-hidroklorida,
(b) dobivanje smjese koja sadrži osigurani epirubicin-hidroklorid i najmanje jedan alkohol, kojeg se bira iz skupine koju čine 1-butanol, 2-butanol i 1-pentanol i
(c) kristaliziranje epirubicin-hidroklorida iz navedene smjese;
gdje smjesa u koraku (b) dodatno sadrži vodu.
2. Postupak u skladu s patentnim zahtjevom 1, naznačen time što se u koraku (a) osigurava otopina epirubicin-hidroklorida.
3. Postupak u skladu s patentnim zahtjevom 2, naznačen time što se osigurava vodena otopina epirubicin-hidroklorida.
4. Postupak u skladu s patentnim zahtjevom 3, naznačen time što je udio epirubicin-hidroklorida 100-400 g/l, po mogućnosti 150-350 g/l, u odnosu na ukupni volumen vodene otopine koja sadrži epirubicin-hidroklorid.
5. Postupak u skladu s patentnim zahtjevom 1, naznačen time što se u koraku (a) epirubicin-hidroklorid osigurava u kristalnom ili amorfnom obliku.
6. Postupak u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što je udio najmanje jednog alkohola, koji se bira iz skupine koju čine 1-butanol, 2-butanol i 1-pentanol, u rasponu od 5-100%, volumno, po mogućnosti u rasponu od 5-50%, volumno, poželjnije u rasponu od 7-15%, volumno, u odnosu na ukupni volumen smjese u koraku (b).
7. Postupak u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što smjesa u koraku (b) sadrži najmanje jedan dodatni alkohol, koji se bira iz skupine koju čine etanol, 1-propanol i 2-propanol.
8. Postupak u skladu s patentnim zahtjevom 7, naznačen time što je udio najmanje jednog dodatnog alkohola, koji se bira iz skupine koju čine etanol, 1-propanol i 2-propanol, u rasponu od 5-95%, volumno, u odnosu na ukupni volumen smjese.
9. Postupak u skladu s patentnim zahtjevom 7 ili 8, naznačen time što je omjer između volumena dodatnog alkohola, koji se bira iz skupine koju čine etanol, 1-propanol i 2-propanol, i volumena alkohola, kojeg se bira iz skupine koju čine 1-butanol, 2-butanol i 1-pentanol, u rasponu od 3:1 do 20:1, poželjnije u rasponu od 5:1 do 15:1, a još poželjnije u rasponu od 7:1 do 10:1.
10. Postupak u skladu s to bilo kojim od prethodnih patentnih zahtjeva, naznačen time što je udio vode u smjesi u rasponu od 0,5-7%, volumno, po mogućnosti u rasponu od 3-5%, volumno, u odnosu na ukupni volumen smjese.
11. Postupak u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što je udio epirubicin-hidroklorida u koraku (b) u rasponu od 5-100 g/l, po mogućnosti u rasponu od 10-50 g/l, poželjnije u rasponu od 25-35 g/l, u odnosu na volumen smjese.
12. Postupak u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što je pH smjese u koraku (b) u rasponu od 2,5-4,5, po mogućnosti u rasponu od 3,0-4,5, poželjnije u rasponu od 3,5-4,5, a još poželjnije u rasponu od 3,9-4,1.
13. Postupak u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što se smjesu u koraku (c) grije do temperature u rasponu od 50-75 °C, po mogućnosti u rasponu od 60-70 °C.
14. Postupak u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što se smjesa drži na rasponu temperatura od 50-75 °C, po mogućnosti u rasponu od 60-70 °C, u trajanju od 2-8 sati, po mogućnosti u trajanju od 4-6 sati.
15. Postupak u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što se dobiveni kristale izdvajaju iz preostale smjese.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102011103751A DE102011103751A1 (de) | 2011-05-31 | 2011-05-31 | Kristallisierung von Epirubicinhydrochlorid |
| US201161493034P | 2011-06-03 | 2011-06-03 | |
| EP12735774.7A EP2714707B1 (de) | 2011-05-31 | 2012-05-25 | Kristallisierung von epirubicinhydrochlorid |
| PCT/EP2012/002248 WO2012163508A1 (de) | 2011-05-31 | 2012-05-25 | Kristallisierung von epirubicinhydrochlorid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20170329T1 true HRP20170329T1 (hr) | 2017-04-21 |
Family
ID=47173398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20170329TT HRP20170329T1 (hr) | 2011-05-31 | 2017-02-27 | Kristaliziranje epirubicin-hidroklorida |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US9657047B2 (hr) |
| EP (1) | EP2714707B1 (hr) |
| JP (2) | JP6014844B2 (hr) |
| KR (1) | KR20140006092A (hr) |
| CN (1) | CN103827129A (hr) |
| AR (1) | AR086519A1 (hr) |
| AU (1) | AU2012265238B2 (hr) |
| DE (1) | DE102011103751A1 (hr) |
| HR (1) | HRP20170329T1 (hr) |
| HU (1) | HUE031795T2 (hr) |
| PL (1) | PL2714707T3 (hr) |
| RU (1) | RU2586117C2 (hr) |
| TW (1) | TWI496789B (hr) |
| WO (1) | WO2012163508A1 (hr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2778171A1 (en) * | 2013-03-15 | 2014-09-17 | Synbias Pharma Ltd. | Crystalline monohydrate of epirubicin hydrochloride |
| CN104861014B (zh) * | 2015-06-03 | 2017-09-29 | 道中道（菏泽）制药有限公司 | 一种盐酸表阿霉素结晶的制备方法 |
| CN109384822B (zh) * | 2017-08-11 | 2021-08-03 | 鲁南制药集团股份有限公司 | 一种盐酸表柔比星晶型及其制备方法 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1506200A (en) | 1975-04-30 | 1978-04-05 | Farmaceutici Italia | Glycosides |
| 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 |
| IT1155446B (it) | 1982-12-23 | 1987-01-28 | Erba Farmitalia | Procedimento per la purificazione di glucosidi antraciclinonici mediante adsobimento selettivo su resine |
| GB8426672D0 (en) | 1984-10-22 | 1984-11-28 | Erba Farmitalia | Pharmaceutical compositions |
| EP0848009B1 (en) | 1996-12-16 | 2000-08-16 | Pharmachemie B.V. | A process for preparing epirubicin or acid addition salts thereof from daunorubicin |
| AU1259899A (en) | 1997-11-28 | 1999-06-16 | Sumitomo Pharmaceuticals Company, Limited | Crystalline amrubicin hydrochloride |
| ES2356284T3 (es) | 1997-12-05 | 2011-04-06 | Mercian Corporation | Antibiótico de antraciclina cristalino y procedimiento para su producción. |
| EP1248869A2 (en) * | 2000-01-07 | 2002-10-16 | Transform Pharmaceuticals, Inc. | High-throughput formation, identification, and analysis of diverse solid-forms |
| WO2005004805A2 (en) * | 2003-07-02 | 2005-01-20 | Solux Corporation | Thermally stable crystalline epirubicin hydrochloride and method of making the same |
| 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 |
| EP1814525A2 (en) * | 2005-05-11 | 2007-08-08 | Sicor Inc. | Stable lyophilized anthracycline glycosides |
| US8802830B2 (en) * | 2005-12-20 | 2014-08-12 | Solux Corporation | Synthesis of epirubicin from 13-dihydrodaunorubicine |
| JP2007261976A (ja) * | 2006-03-28 | 2007-10-11 | Meiji Seika Kaisha Ltd | 抗腫瘍性アンスラサイクリン系抗生物質の製造法 |
| DK1990405T3 (da) | 2007-05-08 | 2017-11-06 | Provivo Oy | Genetisk modificerede stammer, der producerer anthracyclin-metabolitter anvendelige som kræftmedicin |
| JP5550644B2 (ja) | 2008-06-18 | 2014-07-16 | レクシコン ファーマシューティカルズ インコーポレイテッド | （１ｒ，２ｓ，３ｒ）−１−（２−（イソオキサゾール−３−イル）−１ｈ−イミダゾール−４−イル）ブタン−１，２，３，４−テトラオールの固体形態及びその使用方法 |
| EP2301943B1 (en) * | 2009-09-08 | 2014-01-08 | Heraeus Precious Metals GmbH & Co. KG | Crystallization of epidaunorubicin x HCI |
| KR101125460B1 (ko) * | 2010-03-24 | 2012-03-28 | 동아제약주식회사 | 에피루비신 염산염의 신규한 결정형 |
| CN102120750B (zh) * | 2011-01-30 | 2013-04-03 | 山东新时代药业有限公司 | 一种盐酸表柔比星的纯化方法 |
-
2011
- 2011-05-31 DE DE102011103751A patent/DE102011103751A1/de not_active Ceased
-
2012
- 2012-05-15 US US13/471,537 patent/US9657047B2/en active Active
- 2012-05-22 AR ARP120101808A patent/AR086519A1/es not_active Application Discontinuation
- 2012-05-25 RU RU2013158684/04A patent/RU2586117C2/ru active
- 2012-05-25 AU AU2012265238A patent/AU2012265238B2/en active Active
- 2012-05-25 PL PL12735774T patent/PL2714707T3/pl unknown
- 2012-05-25 EP EP12735774.7A patent/EP2714707B1/de active Active
- 2012-05-25 CN CN201280026091.5A patent/CN103827129A/zh active Pending
- 2012-05-25 WO PCT/EP2012/002248 patent/WO2012163508A1/de active Application Filing
- 2012-05-25 JP JP2014513078A patent/JP6014844B2/ja active Active
- 2012-05-25 HU HUE12735774A patent/HUE031795T2/en unknown
- 2012-05-25 KR KR1020137031904A patent/KR20140006092A/ko active Search and Examination
- 2012-05-29 TW TW101119194A patent/TWI496789B/zh active
-
2016
- 2016-05-18 JP JP2016099985A patent/JP2016175938A/ja active Pending
-
2017
- 2017-02-27 HR HRP20170329TT patent/HRP20170329T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2016175938A (ja) | 2016-10-06 |
| TWI496789B (zh) | 2015-08-21 |
| AR086519A1 (es) | 2013-12-18 |
| RU2013158684A (ru) | 2015-07-10 |
| EP2714707B1 (de) | 2016-12-14 |
| CN103827129A (zh) | 2014-05-28 |
| US9657047B2 (en) | 2017-05-23 |
| KR20140006092A (ko) | 2014-01-15 |
| JP2014515381A (ja) | 2014-06-30 |
| US20120309948A1 (en) | 2012-12-06 |
| TW201302773A (zh) | 2013-01-16 |
| DE102011103751A1 (de) | 2012-12-06 |
| JP6014844B2 (ja) | 2016-10-26 |
| HUE031795T2 (en) | 2017-08-28 |
| WO2012163508A1 (de) | 2012-12-06 |
| EP2714707A1 (de) | 2014-04-09 |
| RU2586117C2 (ru) | 2016-06-10 |
| PL2714707T3 (pl) | 2017-06-30 |
| AU2012265238A1 (en) | 2014-01-09 |
| AU2012265238B2 (en) | 2016-05-12 |
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