CH619614A5 - - Google Patents

Download PDF

Info

Publication number: CH619614A5
Authority: CH; Switzerland
Prior art keywords: daunomycin; fab; tumor; drug; compounds
Prior art date: 1975-05-27

Application number

CH652476A

Other languages

German (de)

English (en)

Inventor

Michael Prof Sela

Ruth Prof Arnon

Esther Dr Hurvitz

Ruth Maron

Original Assignee

Yeda Res & Dev

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.)

1975-05-27

Filing date

1976-05-24

Publication date

1980-10-15

1976-05-24 Application filed by Yeda Res & Dev filed Critical Yeda Res & Dev

1980-10-15 Publication of CH619614A5 publication Critical patent/CH619614A5/de

Links

150000001875 compounds Chemical class 0.000 claims description 33
STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound 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(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 claims description 31
STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 claims description 30
WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 claims description 30
230000027455 binding Effects 0.000 claims description 22
230000000259 anti-tumor effect Effects 0.000 claims description 21
239000003814 drug Substances 0.000 claims description 21
230000000694 effects Effects 0.000 claims description 21
210000004027 cell Anatomy 0.000 claims description 20
239000000539 dimer Substances 0.000 claims description 19
229940079593 drug Drugs 0.000 claims description 19
108060003951 Immunoglobulin Proteins 0.000 claims description 16
102000018358 immunoglobulin Human genes 0.000 claims description 16
206010028980 Neoplasm Diseases 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 11
239000000427 antigen Substances 0.000 claims description 10
102000036639 antigens Human genes 0.000 claims description 10
108091007433 antigens Proteins 0.000 claims description 10
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims description 10
108091003079 Bovine Serum Albumin Proteins 0.000 claims description 9
238000000034 method Methods 0.000 claims description 9
239000012634 fragment Substances 0.000 claims description 8
102000004169 proteins and genes Human genes 0.000 claims description 7
108090000623 proteins and genes Proteins 0.000 claims description 7
210000004881 tumor cell Anatomy 0.000 claims description 7
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound 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 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 6
229940098773 bovine serum albumin Drugs 0.000 claims description 6
201000011510 cancer Diseases 0.000 claims description 6
229940072221 immunoglobulins Drugs 0.000 claims description 6
230000001472 cytotoxic effect Effects 0.000 claims description 5
238000000338 in vitro Methods 0.000 claims description 5
229910000033 sodium borohydride Inorganic materials 0.000 claims description 5
239000012279 sodium borohydride Substances 0.000 claims description 5
239000002262 Schiff base Substances 0.000 claims description 4
150000004753 Schiff bases Chemical class 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
239000000203 mixture Substances 0.000 claims description 4
206010025323 Lymphomas Diseases 0.000 claims description 3
229940009456 adriamycin Drugs 0.000 claims description 3
230000000690 anti-lymphoma Effects 0.000 claims description 3
239000002246 antineoplastic agent Substances 0.000 claims description 3
239000000969 carrier Substances 0.000 claims description 3
230000000717 retained effect Effects 0.000 claims description 3
210000001519 tissue Anatomy 0.000 claims description 3
230000001988 toxicity Effects 0.000 claims description 3
231100000419 toxicity Toxicity 0.000 claims description 3
UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims description 2
FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 2
241000700605 Viruses Species 0.000 claims description 2
230000015572 biosynthetic process Effects 0.000 claims description 2
CFCUWKMKBJTWLW-UHFFFAOYSA-N deoliosyl-3C-alpha-L-digitoxosyl-MTM Natural products CC=1C(O)=C2C(O)=C3C(=O)C(OC4OC(C)C(O)C(OC5OC(C)C(O)C(OC6OC(C)C(O)C(C)(O)C6)C5)C4)C(C(OC)C(=O)C(O)C(C)O)CC3=CC2=CC=1OC(OC(C)C1O)CC1OC1CC(O)C(O)C(C)O1 CFCUWKMKBJTWLW-UHFFFAOYSA-N 0.000 claims description 2
229920002521 macromolecule Polymers 0.000 claims description 2
229960000485 methotrexate Drugs 0.000 claims description 2
CFCUWKMKBJTWLW-BKHRDMLASA-N mithramycin Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@H]1O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1C)O[C@@H]1O[C@H](C)[C@@H](O)[C@H](O[C@@H]2O[C@H](C)[C@H](O)[C@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@@](C)(O)C3)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@@H](O)[C@H](O)[C@@H](C)O1 CFCUWKMKBJTWLW-BKHRDMLASA-N 0.000 claims description 2
229960003171 plicamycin Drugs 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims 2
238000004113 cell culture Methods 0.000 claims 1
230000002147 killing effect Effects 0.000 claims 1
210000002751 lymph Anatomy 0.000 claims 1
230000003211 malignant effect Effects 0.000 claims 1
210000005170 neoplastic cell Anatomy 0.000 claims 1
230000009772 tissue formation Effects 0.000 claims 1
231100000331 toxic Toxicity 0.000 claims 1
230000002588 toxic effect Effects 0.000 claims 1
DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 description 8
241000283707 Capra Species 0.000 description 7
230000000144 pharmacologic effect Effects 0.000 description 6
102000057297 Pepsin A Human genes 0.000 description 5
108090000284 Pepsin A Proteins 0.000 description 5
229920005654 Sephadex Polymers 0.000 description 5
239000012507 Sephadex™ Substances 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
229940111202 pepsin Drugs 0.000 description 5
241000283973 Oryctolagus cuniculus Species 0.000 description 4
DRTQHJPVMGBUCF-PSQAKQOGSA-N beta-L-uridine Natural products O[C@H]1[C@@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-PSQAKQOGSA-N 0.000 description 4
231100000433 cytotoxic Toxicity 0.000 description 4
238000010348 incorporation Methods 0.000 description 4
DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 4
229940045145 uridine Drugs 0.000 description 4
241000699670 Mus sp. Species 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
239000012894 fetal calf serum Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
230000007017 scission Effects 0.000 description 3
102000035195 Peptidases Human genes 0.000 description 2
108091005804 Peptidases Proteins 0.000 description 2
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
229910052921 ammonium sulfate Inorganic materials 0.000 description 2
235000011130 ammonium sulphate Nutrition 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
230000003013 cytotoxicity Effects 0.000 description 2
231100000135 cytotoxicity Toxicity 0.000 description 2
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
238000002523 gelfiltration Methods 0.000 description 2
230000002163 immunogen Effects 0.000 description 2
230000002779 inactivation Effects 0.000 description 2
239000002953 phosphate buffered saline Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
210000000952 spleen Anatomy 0.000 description 2
241001515965 unidentified phage Species 0.000 description 2
238000005406 washing Methods 0.000 description 2
WYXSYVWAUAUWLD-SHUUEZRQSA-N 6-azauridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=N1 WYXSYVWAUAUWLD-SHUUEZRQSA-N 0.000 description 1
208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 1
208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 1
208000026310 Breast neoplasm Diseases 0.000 description 1
241000700198 Cavia Species 0.000 description 1
GUGHGUXZJWAIAS-QQYBVWGSSA-N Daunorubicin hydrochloride 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(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 GUGHGUXZJWAIAS-QQYBVWGSSA-N 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
241000701533 Escherichia virus T4 Species 0.000 description 1
102000006395 Globulins Human genes 0.000 description 1
108010044091 Globulins Proteins 0.000 description 1
206010020751 Hypersensitivity Diseases 0.000 description 1
102000018071 Immunoglobulin Fc Fragments Human genes 0.000 description 1
108010091135 Immunoglobulin Fc Fragments Proteins 0.000 description 1
JCYZMTMYPZHVBF-UHFFFAOYSA-N Melarsoprol Chemical compound NC1=NC(N)=NC(NC=2C=CC(=CC=2)[As]2SC(CO)CS2)=N1 JCYZMTMYPZHVBF-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 1
230000006819 RNA synthesis Effects 0.000 description 1
241000700159 Rattus Species 0.000 description 1
206010039491 Sarcoma Diseases 0.000 description 1
208000024313 Testicular Neoplasms Diseases 0.000 description 1
208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
229930013930 alkaloid Natural products 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
230000007815 allergy Effects 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
210000000601 blood cell Anatomy 0.000 description 1
230000037396 body weight Effects 0.000 description 1
210000002798 bone marrow cell Anatomy 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
108091092328 cellular RNA Proteins 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
229960000975 daunorubicin Drugs 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
229940088598 enzyme Drugs 0.000 description 1
210000003743 erythrocyte Anatomy 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
239000000178 monomer Substances 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
201000008968 osteosarcoma Diseases 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000036647 reaction Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000011160 research Methods 0.000 description 1
239000007974 sodium acetate buffer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
210000001541 thymus gland Anatomy 0.000 description 1
239000003643 water by type Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S530/00—Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof
- Y10S530/806—Antigenic peptides or proteins
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S530/00—Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof
- Y10S530/866—Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof involving immunoglobulin or antibody fragment, e.g. fab', fab, fv, fc, heavy chain or light chain

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical & Material Sciences (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Epidemiology (AREA)
Molecular Biology (AREA)
Immunology (AREA)
Biochemistry (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Saccharide Compounds (AREA)
Peptides Or Proteins (AREA)

CH652476A 1975-05-27 1976-05-24 CH619614A5 (el)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IL47372A IL47372A (en)	1975-05-27	1975-05-27	Fab'dimers bound to daunomycin or adriamycin,their preparation and pharmaceutical compositions containing same

Publications (1)

Publication Number	Publication Date
CH619614A5 true CH619614A5 (el)	1980-10-15

Family

ID=11048252

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH652476A CH619614A5 (el)	1975-05-27	1976-05-24

Country Status (11)

Country	Link
US (1)	US4093607A (el)
JP (1)	JPS51144723A (el)
AU (1)	AU512255B2 (el)
CA (1)	CA1064826A (el)
CH (1)	CH619614A5 (el)
DE (1)	DE2623736A1 (el)
FR (1)	FR2312259A1 (el)
GB (1)	GB1523980A (el)
IL (1)	IL47372A (el)
SE (1)	SE437767B (el)
ZA (1)	ZA762966B (el)

Families Citing this family (59)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4263279A (en) *	1975-08-19	1981-04-21	Yeda Research & Development Co. Ltd	Pharmaceutically active compositions containing adriamycin and daunomycin
JPS54132503A (en) *	1978-04-07	1979-10-15	Kayaku Antibiotic Research Co	Immune globulin combined neocarcinostatin
FR2437213A1 (fr) *	1978-09-28	1980-04-25	Cm Ind	Produits cytotoxiques formes par liaison covalente de la chaine a de la ricine avec un anticorps et leur procede de preparation
JPS5665828A (en) *	1979-11-02	1981-06-03	Kureha Chem Ind Co Ltd	Antitumor agent
JPS5665829A (en) *	1979-11-02	1981-06-03	Kureha Chem Ind Co Ltd	Antitumor agent
JPS5592325A (en) *	1978-12-29	1980-07-12	Kureha Chem Ind Co Ltd	Antitumor agent and its preparation
US4315851A (en) *	1978-12-29	1982-02-16	Kureha Kagaku Kogyo Kabushiki Kaisha	Pharmaceutical composition having antitumor activity
JPS55136235A (en) *	1979-04-09	1980-10-23	Teijin Ltd	Antitumor protein complex and its preparation
JPS5616418A (en) *	1979-07-20	1981-02-17	Teijin Ltd	Antitumor protein complex and its preparation
JPS5639022A (en) *	1979-09-05	1981-04-14	Hayashibara Biochem Lab Inc	Preparation of vaccine
JPS57106626A (en) *	1980-12-22	1982-07-02	Teijin Ltd	Cytotoxic protein complex and its preparation
JPS57106625A (en) *	1980-12-22	1982-07-02	Teijin Ltd	Cytotoxic protein complex and its preparation
DE3205847A1 (de) *	1981-05-08	1982-12-16	Farmitalia Carlo Erba S.p.A., 20159 Milano	Daunorubicinprotein-konjugate
US4356170A (en) *	1981-05-27	1982-10-26	Canadian Patents & Development Ltd.	Immunogenic polysaccharide-protein conjugates
US5144011A (en) *	1981-06-26	1992-09-01	Boston University	Acidity-sensitive spacer molecule to control the release of pharmaceuticals from molecular carriers
US4631190A (en) *	1981-06-26	1986-12-23	Shen Wei C	Acidity-sensitive spacer molecule to control the release of pharmaceuticals from molecular carriers
JPH06157346A (ja) *	1981-09-08	1994-06-03	Suntory Ltd	選択性制癌剤
CA1203164A (en) *	1982-03-09	1986-04-15	Thomas J. Mckearn	Antibody conjugates
US4671958A (en) *	1982-03-09	1987-06-09	Cytogen Corporation	Antibody conjugates for the delivery of compounds to target sites
US5140104A (en) *	1982-03-09	1992-08-18	Cytogen Corporation	Amine derivatives of folic acid analogs
US4867973A (en) *	1984-08-31	1989-09-19	Cytogen Corporation	Antibody-therapeutic agent conjugates
US4613459A (en) *	1982-10-20	1986-09-23	Dana-Farber Cancer Institute	Lymphocyte growth factor
JPS59116232A (ja) *	1982-12-24	1984-07-05	Teijin Ltd	細胞毒性複合体及びその製造法
JPH0651643B2 (ja) *	1983-01-19	1994-07-06	帝人株式会社	殺細胞性修飾免疫グロブリン及びその製造方法
JPS59134732A (ja) *	1983-01-21	1984-08-02	Green Cross Corp:The	フイブロネクチン・生理活性物質複合体の製造法
JPS59186924A (ja) *	1983-04-08	1984-10-23	Kureha Chem Ind Co Ltd	ヒト免疫グロブリン結合抗腫瘍剤
JPH0611713B2 (ja) *	1983-04-08	1994-02-16	呉羽化学工業株式会社	ヒト免疫グロブリン結合抗腫瘍剤
GB2148299B (en) *	1983-09-01	1988-01-06	Hybritech Inc	Antibody compositions of therapeutic agents having an extended serum half-life
JPS60246400A (ja) *	1984-05-22	1985-12-06	Ajinomoto Co Inc	アントラサイクリン系化合物及び制ガン剤
PT80662B (en) *	1984-06-20	1986-12-09	Sanofi Sa	Process to obtain anti-tumoral glycoprotein modified on its glycidic portions
FR2566271B1 (fr) *	1984-06-20	1986-11-07	Sanofi Sa	Nouveaux conjugues cytotoxiques utilisables en therapeutique et procede d'obtention
FR2577137B1 (fr) *	1985-02-13	1990-07-13	Sanofi Sa	Glycoproteines antitumorales, modifiees sur leurs motifs glucidiques
FR2577135B1 (fr) *	1985-02-13	1989-12-15	Sanofi Sa	Immunotoxines a longue duree d'action comportant un constituant glycopeptidique inactivant les ribosomes modifie sur ses motifs polysaccharidiques
DE3513572A1 (de) *	1985-04-16	1986-10-16	Karl Prof. Dr.med. 7302 Ostfildern Theurer	Herstellung von praeparaten zur spezifischen beeinflussung der humoralen und zellulaeren immunreaktion
US4911912A (en) *	1985-12-20	1990-03-27	Sanofi	Ribosome-inactivating glycoproteins, modified by oxidation of their osidic units and reduction, and in vivo prolonged-action immunotoxins containing such a glycoprotein
US4911911A (en) *	1985-12-20	1990-03-27	Sanofi	Ribosome-inactivating glycoproteins, modified by oxidation of their osidic units and formation of a schiff's base and in-vivo prolonged action immunotoxins containing such a glycoprotein
FR2591895B1 (fr) *	1985-12-20	1988-08-26	Sanofi Sa	Immunotoxines a longue duree d'action in vivo comportant la chaine a de ricine modifiee sur ses motifs polysaccharidiques
FR2602683B1 (fr) *	1986-08-12	1990-03-30	Sanofi Sa	Immunotoxines a longue duree d'action in vivo comportant une glycoproteine inhibant les ribosomes, modifiee par oxydation des motifs osidiques puis reduction
FR2591894B1 (fr) *	1985-12-20	1988-04-01	Sanofi Sa	Immunotoxines a longue duree d'action in vivo comportant la chaine a de ricine modifiee sur ses motifs polysaccharidiques
JPS62228025A (ja) *	1985-12-27	1987-10-06	Teijin Ltd	抗体複合体の製造方法
US4699784A (en) *	1986-02-25	1987-10-13	Center For Molecular Medicine & Immunology	Tumoricidal methotrexate-antibody conjugate
US4801688A (en) *	1986-05-27	1989-01-31	Eli Lilly And Company	Hydrazone immunoglobulin conjugates
FR2601679B1 (fr) *	1986-07-15	1990-05-25	Sanofi Sa	Immunotoxines, procede de preparation et compositions pharmaceutiques en contenant
US5004606A (en) *	1986-09-24	1991-04-02	Hybritech Incorporated	Non-covalent antibody-anthracycline immunocomplexes
US4994558A (en) *	1986-12-24	1991-02-19	Eli Lilly And Company	Immunoglobulin conjugates
US4814438A (en) *	1986-12-24	1989-03-21	Eli Lilly And Company	Immunoglobulin conjugates of 2',2'-difluronucleosides
EP0329184A3 (en) *	1988-02-19	1990-05-23	Neorx Corporation	Antimers and antimeric conjugation
US5112954A (en) *	1988-02-26	1992-05-12	Neorx Corporation	Method of enhancing the effect of cytotoxic agents
US5066789A (en) *	1988-09-30	1991-11-19	Neorx Corporation	Targeting substance-diagnostic/therapeutic agent conjugates having Schiff base linkages
EP0434765B1 (en) *	1988-09-30	1995-11-08	Neorx Corporation	Targeting substance-diagnostic/therapeutic agent conjugates having schiff base linkages
US6884418B1 (en) *	1989-08-04	2005-04-26	Berlex Laboratories, Inc.	Use of ligand-mimicking agents and anti-neoplastic drugs in cancer therapy
DE4122210C2 (de) *	1991-07-04	1999-04-01	Deutsches Krebsforsch	Konjugate aus tumoraktiver Verbindung und Serumalbumin sowie Verfahren zu deren Herstellung und ihre Verwendung
US5382582A (en) *	1993-03-26	1995-01-17	Chan; Carcy L.	Methotrexate analogs and methods of using same
US5750119A (en) *	1994-01-13	1998-05-12	Mount Sinai School Of Medicine Of The City University Of New York	Immunotherapeutic stress protein-peptide complexes against cancer
US5698556A (en) *	1995-06-07	1997-12-16	Chan; Carcy L.	Methotrexate analogs and methods of using same
US6225063B1 (en)	1998-05-22	2001-05-01	University Technology Corporation	RNA channels in biological membranes
WO2006031614A2 (en) *	2004-09-10	2006-03-23	Tosk, Inc.	Reduced toxicity methotrexate formulations and methods for using the same
NZ592293A (en)	2005-11-28	2012-10-26	Verrow Pharmaceuticals Inc	Compositions comprising an oligosaccharide such as a cyclodextrin for reducing the nephrotoxicity of other drugs
AU2009223453B2 (en)	2008-03-03	2014-05-01	Tosk, Inc.	Methotrexate adjuvants to reduce toxicity and methods for using the same

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1792298A1 (de) *	1968-08-16	1971-07-08	Rand Dev Corp	Immunochromatographische Verteilung von loeslichen Antigenen
DE1814134A1 (de) *	1968-12-12	1970-09-10	Theurer Dr Med Karl	Zusatzverfahren zur Herstellung von arzneimitteln mit selektivem Tropismus
JPS4941526A (el) *	1972-05-15	1974-04-18
DE2322533C2 (de) *	1972-11-06	1986-08-28	Pharmacia AB, Uppsala	Verfahren zum Binden von Immunoglobulin und Hilfsmittel zur Durchführung des Verfahrens
DE2322552C2 (de) *	1972-11-06	1986-08-28	Pharmacia AB, Uppsala	Verfahren zum Abtrennen von Protein A aus Staphylococcus aureus aus einer Flüssigkeit
FR2222083B1 (el) *	1973-03-22	1976-05-14	Fontaine Michel
US3966898A (en) *	1973-06-28	1976-06-29	Pharmacia Diagnostics Ab	Method and reagent for determining immunologic materials
GB1446536A (en) *	1975-02-21	1976-08-18	Yeda Res & Dev	Pharmaceutically active compositions

1975
- 1975-05-27 IL IL47372A patent/IL47372A/xx unknown
1976
- 1976-05-17 GB GB20287/76A patent/GB1523980A/en not_active Expired
- 1976-05-18 ZA ZA762966A patent/ZA762966B/xx unknown
- 1976-05-20 CA CA252,982A patent/CA1064826A/en not_active Expired
- 1976-05-24 CH CH652476A patent/CH619614A5/de not_active IP Right Cessation
- 1976-05-25 SE SE7605942A patent/SE437767B/xx not_active IP Right Cessation
- 1976-05-25 US US05/689,276 patent/US4093607A/en not_active Expired - Lifetime
- 1976-05-25 FR FR7615737A patent/FR2312259A1/fr active Granted
- 1976-05-26 JP JP51061030A patent/JPS51144723A/ja active Granted
- 1976-05-26 DE DE19762623736 patent/DE2623736A1/de not_active Withdrawn
- 1976-05-26 AU AU14321/76A patent/AU512255B2/en not_active Expired

Also Published As

Publication number	Publication date
CA1064826A (en)	1979-10-23
IL47372A (en)	1979-10-31
FR2312259A1 (fr)	1976-12-24
AU512255B2 (en)	1980-10-02
US4093607A (en)	1978-06-06
ZA762966B (en)	1977-05-25
AU1432176A (en)	1977-12-01
IL47372A0 (en)	1975-07-28
SE7605942L (sv)	1976-11-28
DE2623736A1 (de)	1976-12-09
JPH0133448B2 (el)	1989-07-13
JPS51144723A (en)	1976-12-13
GB1523980A (en)	1978-09-06
SE437767B (sv)	1985-03-18
FR2312259B1 (el)	1978-10-20

Publication	Publication Date	Title
CH619614A5 (el)	1980-10-15
DE69434725T2 (de)	2007-05-10	Zell- und Serumproteinanker und Konjugate
DE69838953T2 (de)	2009-01-08	Methoden zur herstellung von glykosylierten antikörpern und antikörperfragmenten mit reaktiven ketongruppen
DE3781946T2 (de)	1993-02-18	Therapeutische oder radiodiagnostische substanz.
DE69231736T2 (de)	2001-10-25	Gerichtete abgabe von genen, die immunogene proteine kodieren
DE3783242T2 (de)	1993-04-29	Aminogruppen enthaltende hochmolekulare verbindungen und deren verwendung.
DE3685625T2 (de)	1993-01-28	Antikoerperkomplexe von haptenmodifizierten diagnostischen oder therapeutischen mitteln.
DE68912232T2 (de)	1994-05-19	Konjugate zytotoxischer Arzneimittel.
CH655010A5 (de)	1986-03-27	Pharmazeutischer wirkstoff mit antitumoraktivitaet.
DE2507901C2 (el)	1990-02-01
DE2744983A1 (de)	1978-04-13	Mehrwertiger antigen-protein-komplex
DE69012747T2 (de)	1995-03-16	Polymyxinkonjugate.
DE3786832T2 (de)	1993-11-11	Verfahren zur Herstellung von Immunoglobulinzubereitungen für intravenöse Injektion.
DE69019959T2 (de)	1995-10-05	Ortspezifische in-vivo-aktivierung von therapeutischen arzneimitteln.
DD201447A5 (de)	1983-07-20	Verfahren zur herstellung von als antikrebsmittel wirksamen immunoglobulin-konjugaten
DE4122210C2 (de)	1999-04-01	Konjugate aus tumoraktiver Verbindung und Serumalbumin sowie Verfahren zu deren Herstellung und ihre Verwendung
DE2541931A1 (de)	1976-04-01	Immunologische verbindungen
DE3320560C2 (el)	1993-09-16
DE194851T1 (de)	1987-03-19	Therapie der menschlichen tumore.
EP0810883A2 (de)	1997-12-10	Konjugat zur individuellen dosierung von arzneimitteln
DE3808166C2 (de)	1997-08-28	Immunglobulinkonjugate, Verfahren zu deren Herstellung sowie pharmazeutische Mittel, die diese enthalten
DE2853453A1 (de)	1980-06-19	Mittel zur therapie von immunkomplexerkrankungen
DE69815769T2 (de)	2004-05-19	Antitumormittel enthaltend einen Komplex einer Oxidoreduktase und eines Polymers und ein Substrat des Enzyms
DE69026387T2 (de)	1996-11-28	Reduktion der nichtzielspezifischen retention von immunokonjugaten und ihren metaboliten
DE2823353A1 (de)	1978-12-21	Verfahren zum reinigen von urokinase

Legal Events

Date	Code	Title	Description
1991-01-31	PL	Patent ceased
2024-10-31	PL	Patent ceased