CA1310637C - Epipodophyllotoxin glucoside 4'-phosphate derivatives - Google Patents

Epipodophyllotoxin glucoside 4'-phosphate derivatives

Info

Publication number
CA1310637C
CA1310637C CA000573861A CA573861A CA1310637C CA 1310637 C CA1310637 C CA 1310637C CA 000573861 A CA000573861 A CA 000573861A CA 573861 A CA573861 A CA 573861A CA 1310637 C CA1310637 C CA 1310637C
Authority
CA
Canada
Prior art keywords
compound
alkyl
substituted
formula
group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
CA000573861A
Other languages
English (en)
French (fr)
Inventor
Mark G. Saulnier
Peter D. Senter
John F. Kadow
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bristol Myers Squibb Co
Original Assignee
Bristol Myers Squibb Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co
Application granted granted Critical
Publication of CA1310637C publication Critical patent/CA1310637C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20Carbocyclic rings
    • C07H15/24Condensed ring systems having three or more rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04Heterocyclic radicals containing only oxygen as ring hetero atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • A61P35/04Antineoplastic 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)
  • Cable Accessories (AREA)
  • Mechanical Coupling Of Light Guides (AREA)
CA000573861A 1987-08-04 1988-08-04 Epipodophyllotoxin glucoside 4'-phosphate derivatives Expired - Lifetime CA1310637C (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US8149387A 1987-08-04 1987-08-04
US081,493 1987-08-04
US07/199,731 US4904768A (en) 1987-08-04 1988-05-27 Epipodophyllotoxin glucoside 4'-phosphate derivatives
US199,731 1988-05-27

Publications (1)

Publication Number Publication Date
CA1310637C true CA1310637C (en) 1992-11-24

Family

ID=26765636

Family Applications (1)

Application Number Title Priority Date Filing Date
CA000573861A Expired - Lifetime CA1310637C (en) 1987-08-04 1988-08-04 Epipodophyllotoxin glucoside 4'-phosphate derivatives

Country Status (34)

Country Link
US (3) US4904768A (enExample)
JP (1) JPH0699465B2 (enExample)
KR (1) KR900006230B1 (enExample)
CN (1) CN1027169C (enExample)
AT (1) AT398974B (enExample)
BE (1) BE1002982A4 (enExample)
CA (1) CA1310637C (enExample)
CH (1) CH676716A5 (enExample)
CY (1) CY1625A (enExample)
CZ (1) CZ286893B6 (enExample)
DD (2) DD274423A5 (enExample)
DE (1) DE3826562A1 (enExample)
DK (2) DK169344B1 (enExample)
ES (1) ES2010775A6 (enExample)
FI (1) FI87790C (enExample)
FR (1) FR2622193B1 (enExample)
GB (1) GB2207674B (enExample)
GR (1) GR1000490B (enExample)
HK (1) HK6392A (enExample)
HU (3) HU208147B (enExample)
IE (1) IE61040B1 (enExample)
IL (1) IL87290A (enExample)
IT (1) IT1226825B (enExample)
LU (2) LU87290A1 (enExample)
MX (1) MX173843B (enExample)
MY (1) MY104321A (enExample)
NL (2) NL192683C (enExample)
NO (4) NO170284C (enExample)
NZ (1) NZ225615A (enExample)
PT (1) PT88186B (enExample)
SE (1) SE502214C2 (enExample)
SG (1) SG101291G (enExample)
SK (1) SK279325B6 (enExample)
YU (3) YU143688A (enExample)

Families Citing this family (64)

* Cited by examiner, † Cited by third party
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
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
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
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
JPH07632B2 (ja) * 1991-12-23 1995-01-11 ブリストル−マイヤーズ スクイブ カンパニー エトポシド4’−ホスフェート二ナトリウム塩の安定な六水和物
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
EP0835303A4 (en) * 1995-06-07 2000-09-13 Univ Jefferson Anti-fungal agents and methods of identifying and using the same
PT907379E (pt) 1996-04-01 2004-09-30 Epix Medical Inc Agentes de contraste bioactivados para imagiologia de diagnostico
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
EP2289549A3 (en) 1999-10-01 2011-06-15 Immunogen, Inc. Immunoconjugates for treating cancer
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
BR0206206A (pt) * 2001-10-26 2005-01-11 Centre Nat Rech Scient Derivados de etoposide e análogos, e composições farmacêuticas contendo os mesmos
EP2281578A3 (en) 2002-07-15 2011-04-13 Board of Regents, The University of Texas System Selected antibodies and duramycin peptides binding to anionic phospholipids and aminophospholipids and their use in treating viral infections and cancer
EP2260874A1 (en) * 2003-01-06 2010-12-15 Angiochem Inc. Aprotinin analogs as carriers across the blood-brain barrier
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
CA2597958C (en) * 2005-02-18 2019-01-15 Angiochem Inc. Molecules for transporting a compound across the blood-brain barrier
US20090016959A1 (en) * 2005-02-18 2009-01-15 Richard Beliveau Delivery of antibodies to the central nervous system
JP5436856B2 (ja) * 2005-07-15 2014-03-05 アンジオケム インコーポレーティッド 薬学的複合体における担体としてのアプロチニンポリペプチドの使用
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
US8263644B2 (en) * 2007-09-13 2012-09-11 Bristol-Myers Squibb Company Cytotoxic xanthone compounds
US8034905B2 (en) 2007-11-09 2011-10-11 Affitech Research, AS Anti-VEGF antibody compositions and methods
BRPI0820722A2 (pt) 2007-12-20 2015-06-16 Novartis Ag Derivados de tiazol usados como inibidores de pi 3 cinases
DK2279008T3 (en) * 2008-04-18 2019-04-29 Angiochem Inc PHARMACEUTICAL COMPOSITIONS OF PACLITAXEL, PACLITAXEL ANALOGS OR PACLITAXEL CONJUGATES AND RELATED PROCEDURES FOR PREPARATION AND 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
CN102245642A (zh) 2008-10-15 2011-11-16 安吉奥开米公司 Glp-1激动剂的结合物及其用途
WO2010063122A1 (en) * 2008-12-05 2010-06-10 Angiochem Inc. Conjugates of neurotensin or neurotensin analogs and uses thereof
CA2747220A1 (en) 2008-12-17 2010-06-24 Richard Beliveau Membrane type-1 matrix metalloprotein inhibitors and uses thereof
CN102510759A (zh) 2009-04-20 2012-06-20 安吉奥开米公司 利用与血管肽-2类似物结合的抗癌剂治疗卵巢癌
JP5932642B2 (ja) 2009-07-02 2016-06-08 アンジオケム インコーポレーテッド 多量体ペプチドコンジュゲートおよびその使用
US8293753B2 (en) 2009-07-02 2012-10-23 Novartis Ag Substituted 2-carboxamide cycloamino ureas
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
US8987257B2 (en) 2011-01-31 2015-03-24 Novartis Ag Heterocyclic derivatives
US9617274B1 (en) 2011-08-26 2017-04-11 Demerx, Inc. Synthetic noribogaine
PT2771342T (pt) 2011-10-28 2016-08-17 Novartis Ag Derivados de purina e o seu uso no tratamento de doença
WO2013085922A1 (en) * 2011-12-09 2013-06-13 Demerx, Inc. Phosphate esters of noribogaine
EP2849756A1 (en) 2012-05-16 2015-03-25 Novartis AG Dosage regimen for a pi-3 kinase inhibitor
EP2934541A4 (en) 2012-12-20 2016-08-03 Demerx Inc NORIBOGAINE SUBSTITUTE
WO2015083101A1 (en) 2013-12-06 2015-06-11 Novartis Ag Dosage regimen for an alpha-isoform selective phosphatidylinositol 3-kinase inhibitor
JP6823055B2 (ja) 2015-06-15 2021-01-27 アンジオケム インコーポレーテッド 軟髄膜癌腫症の治療方法
AU2016347881A1 (en) 2015-11-02 2018-05-10 Novartis Ag Dosage regimen for a phosphatidylinositol 3-kinase inhibitor
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)

* Cited by examiner, † Cited by third party
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
CH481095A (de) * 1966-12-13 1969-11-15 Sandoz Ag Vefahren 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

Also Published As

Publication number Publication date
CH676716A5 (enExample) 1991-02-28
AT398974B (de) 1995-02-27
HK6392A (en) 1992-01-17
SK541288A3 (en) 1998-10-07
NO170284C (no) 1992-09-30
NO170284B (no) 1992-06-22
LU87290A1 (fr) 1990-02-07
CZ541288A3 (cs) 1999-12-15
IT1226825B (it) 1991-02-19
CZ286893B6 (cs) 2000-07-12
IT8821535A0 (it) 1988-07-28
NO1998002I1 (no) 1998-01-14
NL8801934A (nl) 1989-03-01
ATA195588A (de) 1994-07-15
IE882378L (en) 1989-02-04
MY104321A (en) 1994-03-31
KR890003790A (ko) 1989-04-18
NO920277D0 (no) 1992-01-22
JPH01100188A (ja) 1989-04-18
ES2010775A6 (es) 1989-12-01
YU143688A (en) 1990-04-30
NO883299D0 (no) 1988-07-26
US5041424A (en) 1991-08-20
DK11992A (da) 1992-01-31
IL87290A (en) 1993-01-31
DK434088D0 (da) 1988-08-03
YU10490A (en) 1990-06-30
DE3826562C2 (enExample) 1993-04-08
NL970042I1 (nl) 1998-03-02
GB8818462D0 (en) 1988-09-07
DK434088A (da) 1989-02-05
FI87790C (fi) 1993-02-25
NO883299L (no) 1989-02-24
FR2622193B1 (fr) 1993-12-17
HU202547B (en) 1991-03-28
HU208147B (en) 1993-08-30
GB2207674B (en) 1991-09-11
FI87790B (fi) 1992-11-13
IL87290A0 (en) 1989-01-31
HUT47303A (en) 1989-02-28
US4904768A (en) 1990-02-27
NO920277L (no) 1989-02-24
NL192683C (nl) 1997-12-02
GB2207674A (en) 1989-02-08
HU905862D0 (en) 1991-03-28
AU610619B2 (en) 1991-05-23
GR1000490B (el) 1992-07-30
NO172440B (no) 1993-04-13
SE502214C2 (sv) 1995-09-18
FR2622193A1 (fr) 1989-04-28
LU90138I2 (fr) 1997-11-26
NO920665L (no) 1989-02-24
PT88186B (pt) 1995-07-03
BE1002982A4 (fr) 1991-10-15
MX173843B (es) 1994-03-30
SE8802815D0 (sv) 1988-08-03
DK11992D0 (da) 1992-01-31
DE3826562A1 (de) 1989-02-16
PT88186A (pt) 1989-06-30
YU10390A (en) 1990-06-30
KR900006230B1 (ko) 1990-08-27
GR880100512A (en) 1989-05-25
DD299067A5 (de) 1992-03-26
HU211960A9 (en) 1996-01-29
FI883596A0 (fi) 1988-08-01
SG101291G (en) 1992-01-17
USRE35524E (en) 1997-06-03
SE8802815L (sv) 1989-02-05
CY1625A (en) 1992-07-10
DK169344B1 (da) 1994-10-10
DD274423A5 (de) 1989-12-20
CN1027169C (zh) 1994-12-28
NO172440C (no) 1993-07-21
NZ225615A (en) 1991-06-25
AU2030688A (en) 1989-06-08
MX9202851A (es) 1992-06-30
FI883596A7 (fi) 1989-02-05
NO920665D0 (no) 1992-02-20
SK279325B6 (sk) 1998-10-07
NL192683B (enExample) 1997-08-01
IE61040B1 (en) 1994-09-07
JPH0699465B2 (ja) 1994-12-07
CN1061225A (zh) 1992-05-20
NL970042I2 (enExample) 2005-06-01

Similar Documents

Publication Publication Date Title
CA1310637C (en) Epipodophyllotoxin glucoside 4'-phosphate derivatives
AU772478B2 (en) Phosphoramidate, and mono-, DI-, and tri-phosphate esters of (1R,CIS)-4-(6-amino-9H-purin-9-YL)-2-cyclopentene-1- methanol as antiviral agents
US4093714A (en) 9β-D-Arabinofuranosylpurine nucleotides and method of use
WO1984000367A1 (fr) Nouveaux derives de la glycerine pour la synthese de phospholipides
US4958010A (en) Epipodophyllotoxin glucoside lactam derivatives
US6107284A (en) Water-soluble derivatives of epipodophyllotoxin, process for their preparation, their use as medicinal products and their intended use in anti-cancer treatments
CA1306250C (en) 3',4'-dinitrogen substituted epipodophyllotoxin glucoside derivatives
YAEGASHI et al. Chemical Modification of an Antitumor Alkaloid, 20 (S)-Camptothecin: Glycosides, Phosphates and Sulfates of 7-Ethyl 10-hydroxycamptothecin
US3478013A (en) Carbohydrate derivatives of erythromycin
US5026898A (en) Process for regioselectively preparing phosphorylated inositols and other cyclitols
JPS6388194A (ja) 糖燐酸、そのエステル及びそれらの製造法
BG62696B1 (bg) метод за получаване на клиндамицин фосфат

Legal Events

Date Code Title Description
MKEX Expiry