ES2074055T3 - Derivados de amina de antibioticos de antraciclina. - Google Patents

Derivados de amina de antibioticos de antraciclina.

Info

Publication number
ES2074055T3
ES2074055T3 ES88401353T ES88401353T ES2074055T3 ES 2074055 T3 ES2074055 T3 ES 2074055T3 ES 88401353 T ES88401353 T ES 88401353T ES 88401353 T ES88401353 T ES 88401353T ES 2074055 T3 ES2074055 T3 ES 2074055T3
Authority
ES
Spain
Prior art keywords
anthracicline
conjugates
vivo
antibiotics
derivatives
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
ES88401353T
Other languages
English (en)
Inventor
Dalton H King
Daniel J Coughlin
John Dennis Rodwell
Anthony Dwight Lopes
Robert David Radcliffe
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.)
Cytogen Corp
Original Assignee
Cytogen Corp
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
Priority claimed from US07/058,440 external-priority patent/US4950738A/en
Application filed by Cytogen Corp filed Critical Cytogen Corp
Application granted granted Critical
Publication of ES2074055T3 publication Critical patent/ES2074055T3/es
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
    • A61K41/0042—Photocleavage of drugs in vivo, e.g. cleavage of photolabile linkers in vivo by UV radiation for releasing the pharmacologically-active agent from the administered agent; photothrombosis or photoocclusion
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
    • A61K41/0057—Photodynamic therapy with a photosensitizer, i.e. agent able to produce reactive oxygen species upon exposure to light or radiation, e.g. UV or visible light; photocleavage of nucleic acids with an agent
    • 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
    • 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
    • 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
    • A61K47/6889—Conjugates wherein the antibody being the modifying agent and wherein the linker, binder or spacer confers particular properties to the conjugates, e.g. peptidic enzyme-labile linkers or acid-labile linkers, providing for an acid-labile immuno conjugate wherein the drug may be released from its antibody conjugated part in an acidic, e.g. tumoural or environment
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04—Organic compounds
    • A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
    • A61K51/10—Antibodies or immunoglobulins; Fragments thereof, the carrier being an antibody, an immunoglobulin or a fragment thereof, e.g. a camelised human single domain antibody or the Fc fragment of an antibody
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04—Organic compounds
    • A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
    • A61K51/10—Antibodies or immunoglobulins; Fragments thereof, the carrier being an antibody, an immunoglobulin or a fragment thereof, e.g. a camelised human single domain antibody or the Fc fragment of an antibody
    • A61K51/1093—Antibodies or immunoglobulins; Fragments thereof, the carrier being an antibody, an immunoglobulin or a fragment thereof, e.g. a camelised human single domain antibody or the Fc fragment of an antibody conjugates with carriers being antibodies
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
    • G01N33/531—Production of immunochemical test materials
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
    • G01N33/543—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals
    • G01N33/54353—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals with ligand attached to the carrier via a chemical coupling agent
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2121/00—Preparations for use in therapy

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Biochemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Organic Chemistry (AREA)
  • Hematology (AREA)
  • Urology & Nephrology (AREA)
  • Physics & Mathematics (AREA)
  • Biomedical Technology (AREA)
  • Biotechnology (AREA)
  • Pathology (AREA)
  • Cell Biology (AREA)
  • Microbiology (AREA)
  • Genetics & Genomics (AREA)
  • Food Science & Technology (AREA)
  • Analytical Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Biophysics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Communicable Diseases (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

Abstract

LA INVENCION SE REFIERE A NUEVOS DERIVADOS AMINICOS ANTINEOPLASICOS DE ANTIBIOTICOS DE ANTRACICLINA Y A METODOS PARA SINTETIZARLOS. LOS DERIVADOS SON UTILES PARA PREPAR CONJUGADOS DE ANTICUERPOS TERAPEUTICOS UNIDOS A UN SITIO SELECTIVO Y DE ANTIBIOTICO DE ANTRACICLINA QUE RETIENE LA INMUNOESPECIFICIDAD SUSTANCIAL DE LA MOLECULA DE ANTICUERPO CONJUGADO. UTILIZANDO ESTOS CONJUGADOS SE CONSIGUE DESCARGAR EN UN SITIO ESPECIFICO LOS AMINODERIVADOS ANTINEOPLASICOS DEL ANTIBIOTICO DE ANTRACICLINA IN VIVO. DICHOS CONJUGADOS SON TERAPEUTICAMENTE EFICACES CONTRA UNA SERIE DE ALTERACIONES CELULARES NEOPLASICOAS CUANDO SE ADMINSITRAN IN VIVO. TAMBIEN SE INCLUYEN METODOS PARA PREPARAR LOS CONJUGADOS DE ANTICUERPOS Y PARA UTILIZARLOS IN VIVO.
ES88401353T 1987-06-05 1988-06-03 Derivados de amina de antibioticos de antraciclina. Expired - Lifetime ES2074055T3 (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US07/058,440 US4950738A (en) 1984-09-13 1987-06-05 Amine derivatives of anthracycline antibiotics
US07/199,549 US5162512A (en) 1982-03-09 1988-05-27 Amine derivatives of anthracycline antibodies

Publications (1)

Publication Number Publication Date
ES2074055T3 true ES2074055T3 (es) 1995-09-01

Family

ID=26737617

Family Applications (1)

Application Number Title Priority Date Filing Date
ES88401353T Expired - Lifetime ES2074055T3 (es) 1987-06-05 1988-06-03 Derivados de amina de antibioticos de antraciclina.

Country Status (11)

Country Link
US (1) US5162512A (es)
EP (1) EP0294294B1 (es)
JP (1) JPH02500749A (es)
AT (1) ATE122679T1 (es)
AU (1) AU1954988A (es)
DE (1) DE3853792T2 (es)
DK (1) DK51189A (es)
ES (1) ES2074055T3 (es)
FI (1) FI890559A0 (es)
GR (1) GR3017120T3 (es)
WO (1) WO1988009823A1 (es)

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BE1001051A4 (fr) * 1987-03-11 1989-06-20 Erba Carlo Spa Conjugue d'immunoglobuline contenant de l'idarubicine, medicament le contenant et procede de depletion in vitro d'un sous-groupe de lymphocytes t d'une population cellulaire utilisant ce conjugue.
IL89220A (en) * 1988-02-11 1994-02-27 Bristol Myers Squibb Co Anthracycline immunoconjugates, their production and pharmaceutical compositions containing them
CA2016584C (en) * 1989-05-17 1999-06-29 Robert S. Greenfield Anthracycline conjugates having a novel linker and methods for their production
US5137877B1 (en) * 1990-05-14 1996-01-30 Bristol Myers Squibb Co Bifunctional linking compounds conjugates and methods for their production
US5208008A (en) * 1990-11-14 1993-05-04 University Of Pittsburgh Regioselective chemical modification of monoclonal antibodies
JP2698570B2 (ja) * 1991-05-13 1998-01-19 株式会社ディ・ディ・エス研究所 グルタミン酸誘導体の製法
US5228716A (en) * 1991-09-17 1993-07-20 Dahl Gary Michael Convertible transport cart
EP0563795B1 (en) * 1992-03-31 1998-07-22 Dai Nippon Printing Co., Ltd. Enzyme-immobilized electrode, composition for preparation of the same and electrically conductive enzyme
JPH072895A (ja) * 1993-04-28 1995-01-06 Eli Lilly & Co 抗体−薬物複合体
GB9309663D0 (en) * 1993-05-11 1993-06-23 Erba Carlo Spa Biologically active compounds
US6011021A (en) * 1996-06-17 2000-01-04 Guilford Pharmaceuticals Inc. Methods of cancer treatment using naaladase inhibitors
JPH10511340A (ja) * 1995-02-09 1998-11-04 ブリガム アンド ウィメンズ ホスピタル ゲル生成ポリペプチド誘導体
DE69626849T2 (de) * 1995-12-22 2003-12-24 Bristol-Myers Squibb Co., Princeton Verzweigte hydrazongruppen enthaltende kuppler
US6071965A (en) * 1996-06-17 2000-06-06 Guilford Pharmaceuticals Inc. Phosphinic alkanoic acid derivatives
US6054444A (en) 1997-04-24 2000-04-25 Guilford Pharmaceuticals Inc. Phosphonic acid derivatives
US6017903A (en) 1996-09-27 2000-01-25 Guilford Pharmaceuticals Inc. Pharmaceutical compositions and methods of treating a glutamate abnormality and effecting a neuronal activity in an animal using NAALADase inhibitors
US6384022B1 (en) 1996-06-17 2002-05-07 Guilford Pharmaceuticals Inc. Prodrugs of NAALAdase inhibitors
US5824662A (en) * 1996-09-27 1998-10-20 Guilford Pharmaceuticals Inc. Treatment of global and focal ischemia using naaladase inhibitors
NZ333235A (en) 1996-06-17 2000-06-23 Guilford Pharm Inc Methods of cancer treatment using naaladase inhibitors
US5962521A (en) * 1997-04-04 1999-10-05 Guilford Pharmaceuticals Inc. Hydroxamic acid derivatives
CN1230889A (zh) 1996-09-27 1999-10-06 吉尔福特药业有限公司 NAALADase组合物和治疗谷氨酸异常及在动物中产生神经元活性的方法
US5981209A (en) * 1997-12-04 1999-11-09 Guilford Pharmaceuticals Inc. Use of NAALADase activity to identify prostate cancer and benign prostatic hyperplasia
US6028216A (en) * 1997-12-31 2000-02-22 Guilford Pharmaceuticals Inc. Asymmetric syntheses and intermediates for preparing enantiomer-enriched hydroxyphosphinyl derivatives
US6395718B1 (en) 1998-07-06 2002-05-28 Guilford Pharmaceuticals Inc. Pharmaceutical compositions and methods of inhibiting angiogenesis using naaladase inhibitors
US6265609B1 (en) 1998-07-06 2001-07-24 Guilford Pharmaceuticals Inc. Thio-substituted pentanedioic acid derivatives
MXPA01000144A (es) 1998-07-06 2002-10-17 Guilford Pharm Inc Inhibidores de naaladasa utiles como composiciones y compuestos farmaceuticos.
US6444657B1 (en) 1998-12-31 2002-09-03 Guilford Pharmaceuticals Inc. Methods for treating certain diseases using naaladase inhibitors
US6313159B1 (en) 1999-08-20 2001-11-06 Guilford Pharmaceuticals Inc. Metabotropic glutamate receptor ligand derivatives as naaladase inhibitors
AU2002216864A1 (en) * 2000-12-21 2002-07-01 Mcgill University Conjugates of antibodies and anticancer drugs
US7053191B2 (en) * 2003-05-21 2006-05-30 Solux Corporation Method of preparing 4-R-substituted 4-demethoxydaunorubicin
US8357785B2 (en) * 2008-01-08 2013-01-22 Solux Corporation Method of aralkylation of 4′-hydroxyl group of anthracylins
ES2547552T3 (es) 2008-02-01 2015-10-07 Genentech, Inc. Metabolito de nemorrubicina y reactivos análogos, conjugados anticuerpo-fármaco y métodos
MX2011000509A (es) * 2008-07-15 2011-04-05 Genentech Inc Conjugados derivados de antraciclina, proceso para su preparacion y su uso como compuestos antitumorales.
US9850296B2 (en) 2010-08-10 2017-12-26 Ecole Polytechnique Federale De Lausanne (Epfl) Erythrocyte-binding therapeutics
US9517257B2 (en) 2010-08-10 2016-12-13 Ecole Polytechnique Federale De Lausanne (Epfl) Erythrocyte-binding therapeutics
EP2603520A4 (en) 2010-08-10 2014-02-19 Ecole Polytech ERYTHROCYTE BINDING THERAPEUTICS
ES2533710T3 (es) 2010-12-02 2015-04-14 Nerviano Medical Sciences S.R.L. Proceso para la preparación de derivados de morfolinil antraciclina
US8846882B2 (en) 2011-04-29 2014-09-30 Synbias Pharma Ag Method of producing 4-demethoxydaunorubicin
KR20160135214A (ko) 2014-02-21 2016-11-25 에꼴 뽈리떼끄닉 뻬데랄 드 로잔느 (으뻬에프엘) 글리코타겟팅 치료제
US10953101B2 (en) 2014-02-21 2021-03-23 École Polytechnique Fédérale De Lausanne (Epfl) Glycotargeting therapeutics
US10946079B2 (en) 2014-02-21 2021-03-16 Ecole Polytechnique Federale De Lausanne Glycotargeting therapeutics
US10046056B2 (en) 2014-02-21 2018-08-14 École Polytechnique Fédérale De Lausanne (Epfl) Glycotargeting therapeutics
EP3638296A1 (en) 2017-06-16 2020-04-22 The University Of Chicago Compositions and methods for inducing immune tolerance
KR20210010879A (ko) 2018-05-09 2021-01-28 더 유니버서티 오브 시카고 면역 관용 관여 조성물 및 방법
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US4950738A (en) * 1984-09-13 1990-08-21 Cytogen Corporation Amine derivatives of anthracycline antibiotics
US4671958A (en) * 1982-03-09 1987-06-09 Cytogen Corporation Antibody conjugates for the delivery of compounds to target sites
US4460560A (en) * 1982-06-18 1984-07-17 University Of Southern California Drug delivery by polymeric carriers

Also Published As

Publication number Publication date
ATE122679T1 (de) 1995-06-15
FI890559L (fi) 1989-02-06
FI890559A7 (fi) 1989-02-06
GR3017120T3 (en) 1995-11-30
DK51189D0 (da) 1989-02-03
DE3853792T2 (de) 1995-11-30
DE3853792D1 (de) 1995-06-22
EP0294294A3 (en) 1990-05-30
AU1954988A (en) 1989-01-04
EP0294294B1 (en) 1995-05-17
US5162512A (en) 1992-11-10
JPH02500749A (ja) 1990-03-15
DK51189A (da) 1989-02-03
FI890559A0 (fi) 1989-02-06
WO1988009823A1 (en) 1988-12-15
EP0294294A2 (en) 1988-12-07

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