HU202547B - Process for producing epipodophyllotoxin-glycoside-4'-phosphate derivatives and pharmaceutical compositions comprising such active ingredient - Google Patents
Process for producing epipodophyllotoxin-glycoside-4'-phosphate derivatives and pharmaceutical compositions comprising such active ingredient Download PDFInfo
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- HU202547B HU202547B HU884081A HU408188A HU202547B HU 202547 B HU202547 B HU 202547B HU 884081 A HU884081 A HU 884081A HU 408188 A HU408188 A HU 408188A HU 202547 B HU202547 B HU 202547B
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- 238000000034 method Methods 0.000 title claims description 24
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 239000004480 active ingredient Substances 0.000 title description 4
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- 229960005420 etoposide Drugs 0.000 claims description 24
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- 238000002360 preparation method Methods 0.000 claims description 21
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- 239000001257 hydrogen Substances 0.000 claims description 20
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- 150000002431 hydrogen Chemical class 0.000 claims description 15
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- 125000004429 atom Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
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- ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 claims description 3
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- 235000009408 lignans Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000001926 lymphatic effect Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 208000025113 myeloid leukemia Diseases 0.000 description 1
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical compound CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000072 sodium resin Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 201000003120 testicular cancer Diseases 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Mechanical Coupling Of Light Guides (AREA)
- Cable Accessories (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8149387A | 1987-08-04 | 1987-08-04 | |
| US07/199,731 US4904768A (en) | 1987-08-04 | 1988-05-27 | Epipodophyllotoxin glucoside 4'-phosphate derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT47303A HUT47303A (en) | 1989-02-28 |
| HU202547B true HU202547B (en) | 1991-03-28 |
Family
ID=26765636
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU884081A HU202547B (en) | 1987-08-04 | 1988-08-03 | Process for producing epipodophyllotoxin-glycoside-4'-phosphate derivatives and pharmaceutical compositions comprising such active ingredient |
| HU905862A HU208147B (en) | 1987-08-04 | 1988-08-03 | Process for producing etoposide-aminophosphate derivatives |
| HU95P/P00387P HU211960A9 (en) | 1987-08-04 | 1995-06-22 | Epipodophyllotoxinglucosid-4'-phosphat-derivatives |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU905862A HU208147B (en) | 1987-08-04 | 1988-08-03 | Process for producing etoposide-aminophosphate derivatives |
| HU95P/P00387P HU211960A9 (en) | 1987-08-04 | 1995-06-22 | Epipodophyllotoxinglucosid-4'-phosphat-derivatives |
Country Status (34)
Families Citing this family (64)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5191071A (en) * | 1987-08-21 | 1993-03-02 | Novo Nordisk A/S | Monoesters of glycosides and a process for enzymatic preparation thereof |
| US4965348A (en) * | 1989-05-19 | 1990-10-23 | Bristol-Myers Company | Dimeric epipodophyllotoxin glucoside derivatives |
| 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 |
| US6610299B1 (en) | 1989-10-19 | 2003-08-26 | Aventis Pharma Deutschland Gmbh | Glycosyl-etoposide prodrugs, a process for preparation thereof and the use thereof in combination with functionalized tumor-specific enzyme conjugates |
| US6475486B1 (en) | 1990-10-18 | 2002-11-05 | Aventis Pharma Deutschland Gmbh | Glycosyl-etoposide prodrugs, a process for preparation thereof and the use thereof in combination with functionalized tumor-specific enzyme conjugates |
| US7241595B2 (en) | 1989-10-20 | 2007-07-10 | Sanofi-Aventis Pharma Deutschland Gmbh | Glycosyl-etoposide prodrugs, a process for preparation thereof and the use thereof in combination with functionalized tumor-specific enzyme conjugates |
| US5552154A (en) * | 1989-11-06 | 1996-09-03 | The Stehlin Foundation For Cancer Research | Method for treating cancer with water-insoluble s-camptothecin of the closed lactone ring form and derivatives thereof |
| US5034380A (en) * | 1989-11-20 | 1991-07-23 | Bristol-Myers Squibb Company | Alkoxymethylidene epipodophyllotoxin glucosides |
| US5081234A (en) * | 1990-04-30 | 1992-01-14 | Bristol-Myers Squibb Co. | 4'-demethylepipodophyllotoxin glycosides |
| US4997931A (en) * | 1990-06-11 | 1991-03-05 | Bristol-Myers Squibb Company | Epipodophyllotoxin glycosides |
| TW260671B (enExample) * | 1991-04-29 | 1995-10-21 | Bristol Myers Squibb Co | |
| IT1250692B (it) * | 1991-07-23 | 1995-04-21 | Procedimento per la preparazione di demetilepipodofillotossina- beta-d-glucosidi. | |
| US5648474A (en) * | 1991-10-08 | 1997-07-15 | Bristol-Myers Squibb | Crystalline etoposide 4'-phosphate diethanolate |
| CA2085520C (en) * | 1991-12-23 | 1996-07-16 | Uday Shankar Gogate | Stable hexahydrate of etoposide 4'-phosphate disodium salt |
| US6080751A (en) * | 1992-01-14 | 2000-06-27 | The Stehlin Foundation For Cancer Research | Method for treating pancreatic cancer in humans with water-insoluble S-camptothecin of the closed lactone ring form and derivatives thereof |
| 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 |
| FR2725990B1 (fr) * | 1994-10-21 | 1997-01-10 | Pf Medicament | Derives hydrosolubles d'epipodophyllotoxine, leur procede de preparation, leur utilisation a titre de medicament, et leur utilisation destinee aux traitements anticancereux |
| WO1996040886A1 (en) * | 1995-06-07 | 1996-12-19 | Thomas Jefferson University | Anti-fungal agents and methods of identifying and using the same |
| BR9708470A (pt) * | 1996-04-01 | 1999-04-13 | Epix Medical Inc | Agentes de contraste bioativados para formação de imagem para diagnósticos |
| 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 |
| WO1999032499A1 (en) * | 1997-12-23 | 1999-07-01 | Korea Research Institute Of Chemical Technology | 4'-O-DEMETHYL-EPIPODOPHYLLOTOXIN-β-D-GLUCOSIDE ACETAL DERIVATIVES |
| HK1049787B (en) | 1999-10-01 | 2014-07-25 | Immunogen, Inc. | Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents |
| US6624317B1 (en) | 2000-09-25 | 2003-09-23 | The University Of North Carolina At Chapel Hill | Taxoid conjugates as antimitotic and antitumor agents |
| US6506739B1 (en) | 2001-05-01 | 2003-01-14 | Telik, Inc. | Bis-(N,N'-bis-(2-haloethyl)amino)phosphoramidates as antitumor agents |
| CA2464311A1 (en) * | 2001-10-26 | 2003-05-01 | Centre National De La Recherche Scientifique | Derivatives of etoposide and analogs, and pharmaceutical compositions containing them |
| EP2283868B1 (en) | 2002-07-15 | 2016-03-30 | Board of Regents, The University of Texas System | Peptides binding to phosphatidylethanolamine and their use in treating viral infections and cancer |
| ES2368941T3 (es) * | 2003-01-06 | 2011-11-23 | Angiochem Inc. | Angiopep-1, compuestos relacionados y utilizaciones correspondientes. |
| CN100334090C (zh) * | 2005-02-02 | 2007-08-29 | 南京医科大学 | 吡啶类鬼臼毒素化合物及其制备方法和在制备杀虫剂中的应用 |
| RU2408605C2 (ru) * | 2005-02-18 | 2011-01-10 | Анджиокем Инк. | Полипептид, способный преодолевать гематоэнцефалический барьер, и его конъюгат |
| US20090016959A1 (en) * | 2005-02-18 | 2009-01-15 | Richard Beliveau | Delivery of antibodies to the central nervous system |
| PL2233156T3 (pl) * | 2005-07-15 | 2013-09-30 | Angiochem Inc | Zastosowanie polipeptydów aprotyninowych jako nośników w koniugatach farmaceutycznych |
| CN100410266C (zh) * | 2006-01-11 | 2008-08-13 | 重庆华邦制药股份有限公司 | 鬼臼毒素磷酸酯衍生物的合成方法 |
| JO2660B1 (en) | 2006-01-20 | 2012-06-17 | نوفارتيس ايه جي | Pi-3 inhibitors and methods of use |
| PE20070978A1 (es) * | 2006-02-14 | 2007-11-15 | Novartis Ag | COMPUESTOS HETEROCICLICOS COMO INHIBIDORES DE FOSFATIDILINOSITOL 3-QUINASAS (PI3Ks) |
| AR060358A1 (es) * | 2006-04-06 | 2008-06-11 | Novartis Vaccines & Diagnostic | Quinazolinas para la inhibicion de pdk 1 |
| GB0625283D0 (en) * | 2006-12-19 | 2007-01-24 | Cyclacel Ltd | Combination |
| US9365634B2 (en) * | 2007-05-29 | 2016-06-14 | Angiochem Inc. | Aprotinin-like polypeptides for delivering agents conjugated thereto to tissues |
| WO2009036106A1 (en) * | 2007-09-13 | 2009-03-19 | Bristol-Myers Squibb Company | Cytotoxic xanthone compounds |
| MX2010005104A (es) | 2007-11-09 | 2010-08-04 | Peregrine Pharmaceuticals Inc | Composiciones de anticuerpo anti-factor de crecimiento endotelial vascular y metodos. |
| BRPI0820722A2 (pt) | 2007-12-20 | 2015-06-16 | Novartis Ag | Derivados de tiazol usados como inibidores de pi 3 cinases |
| JP5860698B2 (ja) * | 2008-04-18 | 2016-02-16 | アンジオケム，インコーポレーテッド | パクリタキセル、パクリタキセル類似体またはパクリタキセルコンジュゲートの医薬組成物ならびに関連する調製方法および使用方法 |
| EP2346906A4 (en) | 2008-10-15 | 2013-04-24 | Angiochem Inc | CONJUGATES FROM GLP-1 AGONISTS AND THEIR USE |
| JP5705118B2 (ja) | 2008-10-15 | 2015-04-22 | アンジオケム インコーポレーテッド | 薬物送達のためのエトポシドおよびドキソルビシン複合体 |
| JP5759379B2 (ja) * | 2008-12-05 | 2015-08-05 | アンジオケム インコーポレーテッド | ニューロテンシンまたはニューロテンシンアナログおよびその使用 |
| WO2010069074A1 (en) | 2008-12-17 | 2010-06-24 | Universite Du Quebec A Montreal | Membrane type-1 matrix metalloprotein inhibitors and uses thereof |
| EP2421562B1 (en) | 2009-04-20 | 2019-03-13 | Angiochem Inc. | Treatment of ovarian cancer using an anticancer agent conjugated to an angiopep-2 analog |
| US8293753B2 (en) | 2009-07-02 | 2012-10-23 | Novartis Ag | Substituted 2-carboxamide cycloamino ureas |
| RU2012103240A (ru) | 2009-07-02 | 2013-08-10 | Ангиокем Инк. | Мультимерные пептидные конъюгаты и их применение |
| EP2539337A1 (en) | 2010-02-22 | 2013-01-02 | F. Hoffmann-La Roche AG | Pyrido[3,2-d]pyrimidine pi3k delta inhibitor compounds and methods of use |
| US9586954B2 (en) | 2010-06-22 | 2017-03-07 | Demerx, Inc. | N-substituted noribogaine prodrugs |
| AR082418A1 (es) | 2010-08-02 | 2012-12-05 | Novartis Ag | Formas cristalinas de 1-(4-metil-5-[2-(2,2,2-trifluoro-1,1-dimetil-etil)-piridin-4-il]-tiazol-2-il)-amida de 2-amida del acido (s)-pirrolidin-1,2-dicarboxilico |
| MX343706B (es) | 2011-01-31 | 2016-11-18 | Novartis Ag | Derivados heterocíclicos novedosos. |
| US9617274B1 (en) | 2011-08-26 | 2017-04-11 | Demerx, Inc. | Synthetic noribogaine |
| BR112014009890A2 (pt) | 2011-10-28 | 2020-10-27 | Novartis Ag | derivados de purina e seu uso no tratamento de doença |
| CA2855994A1 (en) * | 2011-12-09 | 2013-06-13 | Demerx, Inc. | Phosphate esters of noribogaine |
| BR112014028420A2 (pt) | 2012-05-16 | 2017-09-19 | Novartis Ag | regime de dosagem para um inibidor de quinase pi-3 |
| WO2014098877A1 (en) | 2012-12-20 | 2014-06-26 | Demerx, Inc. | Substituted noribogaine |
| PL3076969T3 (pl) | 2013-12-06 | 2022-01-17 | Novartis Ag | Schemat dawkowania selektywnego inhibitora 3-kinazy fosfatydynozytolu alfa-izoformy |
| CA2989400A1 (en) | 2015-06-15 | 2016-12-22 | Angiochem Inc. | Ang1005 for the treatment of leptomeningeal carcinomatosis |
| MX2018005298A (es) | 2015-11-02 | 2018-06-22 | Novartis Ag | Regimen de dosificacion para un inhibidor de fosfatidilinositol 3-quinasa. |
| WO2018060833A1 (en) | 2016-09-27 | 2018-04-05 | Novartis Ag | Dosage regimen for alpha-isoform selective phosphatidylinositol 3-kinase inhibitor alpelisib |
| KR102378151B1 (ko) | 2020-05-11 | 2022-03-24 | 주식회사 제이앤씨사이언스 | 베타-아포피크로포도필린의 신규한 유도체 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1171314A (fr) * | 1955-05-13 | 1959-01-23 | Sandoz Ag | Produits de condensation de glucosides avec des composés carbonyliques et leur préparation |
| NL6613143A (enExample) * | 1965-09-21 | 1967-03-22 | ||
| CH464957A (de) * | 1965-12-14 | 1968-11-15 | Sandoz Ag | Verfahren zur Herstellung eines neuen Glucosids |
| CH481094A (de) * | 1966-12-13 | 1969-11-15 | Sandoz Ag | Verfahren zur Herstellung neuer Glucoside |
| CH514578A (de) * | 1968-02-27 | 1971-10-31 | Sandoz Ag | Verfahren zur Herstellung von Glucosiden |
| CH543502A (de) * | 1970-11-20 | 1973-10-31 | Sandoz Ag | Verfahren zur Herstellung neuer Glucoside |
| GB1395820A (en) * | 1971-06-05 | 1975-05-29 | Villax I | Preparation of 21-inorganic esters of corticosteroids and salts thereof |
| CH589668A5 (en) * | 1973-06-07 | 1977-07-15 | Sandoz Ag | Cytostatic (4')-demethyl substd. epipodophyllotoxin - prepd. from the corresp. glucopyranoside with (3)-thiophene-carboxaldehyde |
| FR2397425A1 (fr) * | 1977-07-11 | 1979-02-09 | Rhone Poulenc Ind | Nouveaux derives de la daunorubicine, leur preparation et les compositions qui les contiennent |
| DE3374317D1 (en) * | 1982-11-26 | 1987-12-10 | Nippon Kayaku Kk | Process for producing 4'-demethyl-epipodophyllotoxin-beta-d-ethylidene-glucoside and acyl-derivative thereof |
| US4567253A (en) * | 1984-02-03 | 1986-01-28 | Tony Durst | 2-Substituted derivatives of podophyllotoxin and etoposide |
| JPS60208910A (ja) * | 1984-03-31 | 1985-10-21 | Green Cross Corp:The | 水難溶性薬物・リン脂質複合体の製造方法 |
| JPS60246393A (ja) * | 1984-05-22 | 1985-12-06 | Nippon Kayaku Co Ltd | エトポシドの新規製造法 |
| US4739046A (en) * | 1985-08-19 | 1988-04-19 | Luzio Nicholas R Di | Soluble phosphorylated glucan |
| IL77334A (en) * | 1985-12-16 | 1991-04-15 | Univ Bar Ilan | Synthesis of 9-epipodophyllotoxin glucoside derivatives and some novel intermediates therefor |
| US4916217A (en) * | 1987-01-08 | 1990-04-10 | Bristol-Myers Company | Phosphorus containing derivatives of epipodophyllotoxin |
| JPS63192793A (ja) * | 1987-02-06 | 1988-08-10 | Nippon Kayaku Co Ltd | ４′−デメチル−エピポドフイロトキシン誘導体の新規エステル |
| US4874851A (en) * | 1987-07-01 | 1989-10-17 | Bristol-Meyers Company | 3',4'-dinitrogen substituted epipodophyllotoxin glucoside derivatives |
-
1988
- 1988-05-27 US US07/199,731 patent/US4904768A/en not_active Ceased
- 1988-07-21 MY MYPI88000819A patent/MY104321A/en unknown
- 1988-07-22 LU LU87290A patent/LU87290A1/fr active Protection Beyond IP Right Term
- 1988-07-25 YU YU01436/88A patent/YU143688A/xx unknown
- 1988-07-26 NO NO883299A patent/NO170284C/no not_active IP Right Cessation
- 1988-07-28 IT IT8821535A patent/IT1226825B/it active
- 1988-07-29 FR FR8810258A patent/FR2622193B1/fr not_active Expired - Lifetime
- 1988-07-29 NZ NZ225615A patent/NZ225615A/en unknown
- 1988-08-01 FI FI883596A patent/FI87790C/fi not_active IP Right Cessation
- 1988-08-01 IL IL87290A patent/IL87290A/xx not_active IP Right Cessation
- 1988-08-02 SK SK5412-88A patent/SK541288A3/sk unknown
- 1988-08-02 CZ CS19885412A patent/CZ286893B6/cs not_active IP Right Cessation
- 1988-08-03 HU HU884081A patent/HU202547B/hu unknown
- 1988-08-03 DD DD88326917A patent/DD299067A5/de unknown
- 1988-08-03 HU HU905862A patent/HU208147B/hu unknown
- 1988-08-03 ES ES8802434A patent/ES2010775A6/es not_active Expired
- 1988-08-03 DD DD88318652A patent/DD274423A5/de unknown
- 1988-08-03 PT PT88186A patent/PT88186B/pt not_active IP Right Cessation
- 1988-08-03 KR KR1019880009910A patent/KR900006230B1/ko not_active Expired
- 1988-08-03 NL NL8801934A patent/NL192683C/nl not_active IP Right Cessation
- 1988-08-03 AT AT0195588A patent/AT398974B/de active
- 1988-08-03 BE BE8800898A patent/BE1002982A4/fr not_active IP Right Cessation
- 1988-08-03 DK DK434088A patent/DK169344B1/da not_active IP Right Cessation
- 1988-08-03 JP JP63194307A patent/JPH0699465B2/ja not_active Expired - Lifetime
- 1988-08-03 IE IE237888A patent/IE61040B1/en not_active IP Right Cessation
- 1988-08-03 GB GB8818462A patent/GB2207674B/en not_active Expired - Lifetime
- 1988-08-03 SE SE8802815A patent/SE502214C2/sv not_active IP Right Cessation
- 1988-08-04 DE DE3826562A patent/DE3826562A1/de active Granted
- 1988-08-04 CA CA000573861A patent/CA1310637C/en not_active Expired - Lifetime
- 1988-08-04 GR GR880100512A patent/GR1000490B/el not_active IP Right Cessation
- 1988-08-04 CH CH2962/88A patent/CH676716A5/de not_active IP Right Cessation
-
1989
- 1989-12-14 US US07/450,718 patent/US5041424A/en not_active Expired - Lifetime
-
1990
- 1990-01-19 YU YU00104/90A patent/YU10490A/xx unknown
- 1990-01-19 YU YU00103/90A patent/YU10390A/xx unknown
-
1991
- 1991-10-30 CN CN91108384A patent/CN1027169C/zh not_active Expired - Lifetime
- 1991-11-29 SG SG1012/91A patent/SG101291G/en unknown
-
1992
- 1992-01-16 HK HK63/92A patent/HK6392A/xx not_active IP Right Cessation
- 1992-01-22 NO NO920277A patent/NO920277D0/no unknown
- 1992-01-31 DK DK011992A patent/DK11992A/da not_active Application Discontinuation
- 1992-02-20 NO NO920665A patent/NO172440C/no not_active IP Right Cessation
- 1992-06-12 MX MX9202851A patent/MX173843B/es unknown
- 1992-07-10 CY CY1625A patent/CY1625A/en unknown
-
1994
- 1994-04-19 US US08/229,659 patent/USRE35524E/en not_active Expired - Lifetime
-
1995
- 1995-06-22 HU HU95P/P00387P patent/HU211960A9/hu unknown
-
1997
- 1997-09-24 LU LU90138C patent/LU90138I2/fr unknown
- 1997-12-05 NL NL970042C patent/NL970042I1/nl unknown
-
1998
- 1998-01-14 NO NO1998002C patent/NO1998002I1/no unknown
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