FI71942B - Foerfarande foer framstaellning av 4'-demetyl-epipodofyllotoxin-beta-d-etyliden-glukosid och mellanprodukt som anvaends vi foerfarandet - Google Patents
Foerfarande foer framstaellning av 4'-demetyl-epipodofyllotoxin-beta-d-etyliden-glukosid och mellanprodukt som anvaends vi foerfarandet Download PDFInfo
- Publication number
- FI71942B FI71942B FI833334A FI833334A FI71942B FI 71942 B FI71942 B FI 71942B FI 833334 A FI833334 A FI 833334A FI 833334 A FI833334 A FI 833334A FI 71942 B FI71942 B FI 71942B
- Authority
- FI
- Finland
- Prior art keywords
- compound
- formula
- haloacetyl
- demethyl
- ethylidene
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (13)
1. Förfarande för framställnining av 4'-demetyl-epi-podofyllotoxin- β~ D-etyliden-glukosid med formeln (II) -3-γ>Λ „ HO ' f u OH I ίο / Ύ^ΙΓι^ο (id \o^VV z O CH 3°-—^jl~OCH 3 OH 15 kännetecknat därav, att man (A) reagerar 4'-halogenacetyl-4'-demetyl-epipodofyllotoxin-β-D-2,3-di-0-halogenacetyl-4,6-O-etylidenglukosid med formeln (I) “3Τ°Λ0 °χ>\ RO OR I (I)
25 V / CII30—ζ]Ι—OCH3 OR 30 väri R betecknar en halogenacetylgrupp med formeln -COCH2X/ väri X är en halogenatom, med en amin och/eller ammoniak för avlägsnande av halogen-acetylgrupperna i formeln (I), eller 35 (B) utsätter nämnda 4'-halogenacetyl-4'-demetyl-epipodo- fyllotoxin-β-D-2,3-di-0-halogenacetyl-4,6-O-etylidenglu- 20 71 942 kosid för alkoholys i närvaro av en katalysator för av-lägsnande av de nämnda halogenacetylgrupperna, för er-hällande av 4'-demetyl-epipodofyllotoxin-^β-D-etyliden-glukosid. 5 2. Förfarande enligt patentkravet 1, kanne- t e c k n a t därav, att X är klor eller brom.
3. Förfarande enligt patentkravet 1 eller 2, kännetecknat därav, att halogenacetylgrupperna i föreningen med formeln (I) avlägsnas genom reage- 10 rande av föreningen med formeln (I) med en amin och/eller ammoniak.
4. Förfarande enligt patentkravet 3, kännetecknat därav, att aminen är metylamin, etylamin, n-propylamin, n-butylamin, dimetylamin, dietylamin, di- 15 n-propylamin, di-n-butylamin, pyrrolidin, piperidin, raor-folin eller etylendiamin.
5. Förfarande enligt patentkravet 3 eller 4, kännetecknat därav, att reaktionen utföres vid en temperatur av frän -10° tili 100°C. 20 6. Förfarande enligt patentkravet 1 eller 2, kännetecknat därav, att halogenacetylgrupperna i föreningen med formeln (I) avlägsnas genom utsätt-ande av föreningen med formeln (I) för alkoholys i närvaro av en katalysator. 25 7. Förfarande enligt patentkravet 6, känne tecknat därav, att katalysatorn är en eller flera än en förening som valts bland zinkklorid, zinkacetat, zinknitrat, zinkpulver, blyacetat, blypulver, kadmium-acetat, koboltacetat, magnesiumacetat, kalciumacetat, 30 strontiumacetat, bariumacetat och ceriumacetat.
8. Förfarande enligt patentkravet 6 eller 7, kännetecknat därav, att alkoholysen utföres i metanol, etanol eller propanol.
9. Förfarande enligt nägot av patentkraven 6, 7 35 och 8, kännetecknat därav, att alkoholysen utförts vid en temperatur av 40-100°C. 21 71942
1 O . 4 ' -Halogenacetyl-4'-demetyl-epipodofyllotoxin-β-D-2,3-di-0-halogenacetyl-4,6-0-etyliden-glukosid, kännetecknad därav, att den har formeln: RO^ or J /orVr° 10 ch3o^Loch3 OR väri R betecknar en halogenacetylgrupp med formeln -COCH-,Χ, 15 väri X är en halogenatom.
11. Förening enligt patentkravet 10, kännetecknad därav, att X är klor eller brom.
12. Användning av 4'-halogenacetyl-4'-demetyl-epipodof yl lotoxin- β-D-2,3-di-0-halogenacetyl-4,6-O-etyliden- 20 glukosid med formeln (I) οη^οΛ „ RO OR I COCQ Λ 0 CH^O-^y-OCII-J I J 30 0R väri R betecknar en halogenacetylgrupp med formeln -C0CH2X, väri X är en halogenatom, för framställning av 4'-demetyl-epipodof yllotoxin- ^-D-etyliden-glukosid med formeln (II) 35
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP20618882 | 1982-11-26 | ||
JP20618882A JPS5998098A (ja) | 1982-11-26 | 1982-11-26 | 4′―デメチル―エピポドフィロトキシン―β―D―エチリデングルコシドの新規製造法 |
JP8586883 | 1983-05-18 | ||
JP8586883A JPS59212500A (ja) | 1983-05-18 | 1983-05-18 | 4′−デメチル−エピポドフイロトキシン−β−D−エチリデングルコシドの新規製造法 |
Publications (4)
Publication Number | Publication Date |
---|---|
FI833334A0 FI833334A0 (fi) | 1983-09-19 |
FI833334A FI833334A (fi) | 1984-05-27 |
FI71942B true FI71942B (fi) | 1986-11-28 |
FI71942C FI71942C (sv) | 1987-03-09 |
Family
ID=26426870
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI833334A FI71942C (sv) | 1982-11-26 | 1983-09-19 | Förfarande för framställning av 4'-demetyl-epipodofyllotoxin- -D-etyl iden-glukosid och mellanprodukt som används vid förfarandet. |
Country Status (7)
Country | Link |
---|---|
US (1) | US4564675A (sv) |
EP (1) | EP0111058B1 (sv) |
KR (1) | KR890000763B1 (sv) |
DE (1) | DE3374317D1 (sv) |
DK (1) | DK157031C (sv) |
ES (1) | ES525743A0 (sv) |
FI (1) | FI71942C (sv) |
Families Citing this family (41)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS60246393A (ja) * | 1984-05-22 | 1985-12-06 | Nippon Kayaku Co Ltd | エトポシドの新規製造法 |
AU582758B2 (en) * | 1984-06-28 | 1989-04-13 | Mect Corporation | Sialic acid derivatives, galactose derivatives and method for producing the same |
US4895727A (en) * | 1985-05-03 | 1990-01-23 | Chemex Pharmaceuticals, Inc. | Pharmaceutical vehicles for exhancing penetration and retention in the skin |
IL77334A (en) * | 1985-12-16 | 1991-04-15 | Univ Bar Ilan | Synthesis of 9-epipodophyllotoxin glucoside derivatives and some novel intermediates therefor |
WO1988003799A1 (en) * | 1986-11-19 | 1988-06-02 | Chemex Pharmaceuticals, Inc. | Pharmaceutical vehicles for reducing transdermal flux |
US4916217A (en) * | 1987-01-08 | 1990-04-10 | Bristol-Myers Company | Phosphorus containing derivatives of epipodophyllotoxin |
US5716990A (en) * | 1987-03-09 | 1998-02-10 | Cancer Research Campaign Technology Limited | Drug delivery systems |
US4874851A (en) * | 1987-07-01 | 1989-10-17 | Bristol-Meyers Company | 3',4'-dinitrogen substituted epipodophyllotoxin glucoside derivatives |
US4904768A (en) * | 1987-08-04 | 1990-02-27 | Bristol-Myers Company | Epipodophyllotoxin glucoside 4'-phosphate derivatives |
US4975278A (en) * | 1988-02-26 | 1990-12-04 | Bristol-Myers Company | Antibody-enzyme conjugates in combination with prodrugs for the delivery of cytotoxic agents to tumor cells |
US4868291A (en) * | 1987-08-20 | 1989-09-19 | Bristol-Myers Company | 4'-deshydroxyepipodophyllotoxin glucosides: synthesis and use |
US4935504A (en) * | 1987-12-18 | 1990-06-19 | Bristol-Myers Company | Epipodophyllotoxin glucoside 4'-acyl derivatives |
ZA886810B (en) * | 1987-12-18 | 1989-08-30 | Bristol Myers Co | Epipodophyllotoxin glucoside 4'-acyl derivatives |
US4958010A (en) * | 1988-02-16 | 1990-09-18 | Bristol-Myers Company | Epipodophyllotoxin glucoside lactam derivatives |
US5632990A (en) * | 1988-04-22 | 1997-05-27 | Cancer Research Campaign Tech. Ltd. | Treatment for tumors comprising conjugated antibody A5B7 and a prodrug |
US4912204A (en) * | 1988-09-06 | 1990-03-27 | Bristol-Myers Company | Fluoro-substituted epipodophyllotoxin glucosides |
US5061791A (en) * | 1988-12-21 | 1991-10-29 | Warner-Lambert Company | 4-bromo-4'-demethylepipodophyllotoxin derivatives |
DE3913326A1 (de) * | 1989-04-22 | 1990-11-08 | Behringwerke Ag | Verfahren zur herstellung von etoposiden |
US5036055A (en) * | 1989-06-07 | 1991-07-30 | Bristol-Myers Company | Acylated derivatives of etoposide |
US5066645A (en) * | 1989-09-01 | 1991-11-19 | Bristol-Myers Company | Epipodophyllotoxin altroside derivatives |
FR2658824B1 (fr) * | 1990-02-27 | 1992-07-03 | Pf Medicament | Tris acetyl-2",3",4' ethylidene-4",6" beta-d-glucopyranosides, leur preparation et leur utilisation pour la preparation d'ethylidene beta-d-glucopyranoside de demethyl-4' epipodophyllotoxine. |
US5081234A (en) * | 1990-04-30 | 1992-01-14 | Bristol-Myers Squibb Co. | 4'-demethylepipodophyllotoxin glycosides |
IT1250692B (it) * | 1991-07-23 | 1995-04-21 | Procedimento per la preparazione di demetilepipodofillotossina- beta-d-glucosidi. | |
JP3061476B2 (ja) * | 1992-04-24 | 2000-07-10 | 日本化薬株式会社 | エトポシド燐酸エステルの製造法 |
US5459248A (en) * | 1993-11-04 | 1995-10-17 | Bristol-Myers Squibb Company | Process of preparing etoposide phosphate and etoposide |
US5463040A (en) * | 1994-06-28 | 1995-10-31 | Teva Pharmaceutical Industries, Ltd. | Method of preparing etoposide |
US6207673B1 (en) | 1997-03-12 | 2001-03-27 | The University Of North Carolina At Chapel Hill | Covalent conjugates of topoisomerase I and topoisomerase II inhibitors |
US20040072889A1 (en) * | 1997-04-21 | 2004-04-15 | Pharmacia Corporation | Method of using a COX-2 inhibitor and an alkylating-type antineoplastic agent as a combination therapy in the treatment of neoplasia |
CN1376159A (zh) | 1998-09-10 | 2002-10-23 | 加拿大植原药物公司 | 抗肿瘤药亿妥谱赛的制造方法 |
US6756063B2 (en) | 2001-03-29 | 2004-06-29 | Zoltan Laboratories, Llc | Methods and compositions for the treatment of human and animal cancers |
US7200207B2 (en) * | 2004-03-13 | 2007-04-03 | Intrado Inc. | Communication network for providing emergency services |
AU2006207321B2 (en) | 2005-01-21 | 2012-09-06 | Astex Therapeutics Limited | Pharmaceutical compounds |
EP2073807A1 (en) | 2006-10-12 | 2009-07-01 | Astex Therapeutics Limited | Pharmaceutical combinations |
US8916552B2 (en) | 2006-10-12 | 2014-12-23 | Astex Therapeutics Limited | Pharmaceutical combinations |
EP2750683B2 (en) | 2011-10-03 | 2021-01-06 | Croda International PLC | Nanoparticles, process for preparation and use thereof as carrier for amphipatic of hydrophobic molecules in fields of medicine including cancer treatment and food related compounds |
CN102603762A (zh) * | 2012-02-14 | 2012-07-25 | 上海金和生物技术有限公司 | 一种依托泊甙中间体的制备方法 |
WO2014163558A1 (en) | 2013-04-01 | 2014-10-09 | Moreinx Ab | Nanoparticles, composed of sterol and saponin from quillaja saponaria molina process for preparation and use thereof as carrier for amphipatic of hydrphobic molecules in fields of medicine including cancer treatment and food related compounds |
CN108129525B (zh) * | 2017-12-28 | 2019-11-22 | 山东铂源药业有限公司 | 一种依托泊苷中间体的制备方法 |
EP3616688A1 (en) | 2018-08-27 | 2020-03-04 | Centre National de la Recherche Scientifique - CNRS | Preparation of nanosuspension comprising nanocrystals of active pharmaceutical ingredients with little or no stabilizing agents |
EP3669890A1 (en) | 2018-12-18 | 2020-06-24 | Croda International PLC | Filamentous nanoparticles having vaccine adjuvant effect |
CN115141208B (zh) * | 2022-08-05 | 2024-03-08 | 贵州大学 | 一种含各类酯基结构的鬼臼毒素类化合物及其制备方法和应用 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL6613143A (sv) * | 1965-09-21 | 1967-03-22 | ||
CH514578A (de) * | 1968-02-27 | 1971-10-31 | Sandoz Ag | Verfahren zur Herstellung von Glucosiden |
US4147860A (en) * | 1976-07-13 | 1979-04-03 | E. I. Du Pont De Nemours And Company | Process for preparing nitroaromatic glycosides |
-
1983
- 1983-09-03 DE DE8383108701T patent/DE3374317D1/de not_active Expired
- 1983-09-03 EP EP83108701A patent/EP0111058B1/en not_active Expired
- 1983-09-06 US US06/529,749 patent/US4564675A/en not_active Expired - Lifetime
- 1983-09-12 KR KR1019830004276A patent/KR890000763B1/ko not_active IP Right Cessation
- 1983-09-19 DK DK425583A patent/DK157031C/da not_active IP Right Cessation
- 1983-09-19 ES ES525743A patent/ES525743A0/es active Granted
- 1983-09-19 FI FI833334A patent/FI71942C/sv not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
DE3374317D1 (en) | 1987-12-10 |
EP0111058B1 (en) | 1987-11-04 |
US4564675A (en) | 1986-01-14 |
DK157031C (da) | 1990-03-26 |
DK425583A (da) | 1984-05-27 |
ES8506324A1 (es) | 1985-07-01 |
ES525743A0 (es) | 1985-07-01 |
EP0111058A1 (en) | 1984-06-20 |
FI71942C (sv) | 1987-03-09 |
DK157031B (da) | 1989-10-30 |
FI833334A (fi) | 1984-05-27 |
KR840006672A (ko) | 1984-12-01 |
DK425583D0 (da) | 1983-09-19 |
KR890000763B1 (ko) | 1989-04-05 |
FI833334A0 (fi) | 1983-09-19 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM | Patent lapsed |
Owner name: NIPPON KAYAKU KABUSHIKI KAISHA |