CA2021942C - Couplage d'un agent anti-tumoral a un anticorps au moyen d'une glytaraldehyde preactivee - Google Patents

Couplage d'un agent anti-tumoral a un anticorps au moyen d'une glytaraldehyde preactivee Download PDF

Info

Publication number: CA2021942C
Authority: CA; Canada
Prior art keywords: daunorubicin; glutaraldehyde; antibody; conjugate; doxorubicin
Prior art date: 1989-08-10
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

CA002021942A

Other languages

English (en)

Other versions

CA2021942A1 (fr

Inventor

Michel Page

Denis Thibeault

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.)

Bioxel Pharma Inc

Original Assignee

Bioxel Pharma Inc

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.)

1989-08-10

Filing date

1990-07-25

Publication date

2001-04-10

1990-07-25 Application filed by Bioxel Pharma Inc filed Critical Bioxel Pharma Inc

1991-02-11 Publication of CA2021942A1 publication Critical patent/CA2021942A1/fr

2001-04-10 Application granted granted Critical

2001-04-10 Publication of CA2021942C publication Critical patent/CA2021942C/fr

2010-07-25 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000002246 antineoplastic agent Substances 0.000 title claims abstract description 28
SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 title claims description 13
230000000259 anti-tumor effect Effects 0.000 title abstract description 6
230000008878 coupling Effects 0.000 title description 7
238000010168 coupling process Methods 0.000 title description 7
238000005859 coupling reaction Methods 0.000 title description 7
229960000975 daunorubicin Drugs 0.000 claims abstract description 46
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 abstract description 43
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 abstract description 34
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 abstract description 30
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PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
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125000003172 aldehyde group Chemical group 0.000 description 2
231100000360 alopecia Toxicity 0.000 description 2
229940045799 anthracyclines and related substance Drugs 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
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239000012909 foetal bovine serum Substances 0.000 description 2
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239000001570 sorbitan monopalmitate Substances 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
NAALWFYYHHJEFQ-ZASNTINBSA-N (2s,5r,6r)-6-[[(2r)-2-[[6-[4-[bis(2-hydroxyethyl)sulfamoyl]phenyl]-2-oxo-1h-pyridine-3-carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N([C@@H](C(=O)N[C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C=1C=CC(O)=CC=1)C(=O)C(C(N1)=O)=CC=C1C1=CC=C(S(=O)(=O)N(CCO)CCO)C=C1 NAALWFYYHHJEFQ-ZASNTINBSA-N 0.000 description 1
YOFDHOWPGULAQF-MQJDWESPSA-N (7s,9s)-9-acetyl-6,7,9,11-tetrahydroxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical class C1[C@@](O)(C(C)=O)C[C@H](O)C2=C1C(O)=C1C(=O)C(C=CC=C3OC)=C3C(=O)C1=C2O YOFDHOWPGULAQF-MQJDWESPSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
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239000005695 Ammonium acetate Substances 0.000 description 1
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108091003079 Bovine Serum Albumin Proteins 0.000 description 1
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BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
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208000010747 Hodgkins lymphoma Diseases 0.000 description 1
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208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
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JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
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BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical class N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
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Classifications

- 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
- A61K47/6835—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 the modifying agent being an antibody or an immunoglobulin bearing at least one antigen-binding site
- A61K47/6851—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 the modifying agent being an antibody or an immunoglobulin bearing at least one antigen-binding site the antibody targeting a determinant of a tumour cell
- A61K47/6853—Carcino-embryonic antigens
- 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
- A61K47/62—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 a protein, peptide or polyamino acid
- A61K47/65—Peptidic linkers, binders or spacers, e.g. peptidic enzyme-labile linkers
- 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

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Cell Biology (AREA)
Immunology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Oncology (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

CA002021942A 1989-08-10 1990-07-25 Couplage d'un agent anti-tumoral a un anticorps au moyen d'une glytaraldehyde preactivee Expired - Lifetime CA2021942C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US39192889A	1989-08-10	1989-08-10
US391,928		1989-08-10

Publications (2)

Publication Number	Publication Date
CA2021942A1 CA2021942A1 (fr)	1991-02-11
CA2021942C true CA2021942C (fr)	2001-04-10

Family

ID=23548555

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002021942A Expired - Lifetime CA2021942C (fr)	1989-08-10	1990-07-25	Couplage d'un agent anti-tumoral a un anticorps au moyen d'une glytaraldehyde preactivee

Country Status (2)

Country	Link
CA (1)	CA2021942C (fr)
WO (1)	WO1991001757A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19636889A1 (de)	1996-09-11	1998-03-12	Felix Dr Kratz	Antineoplastisch wirkende Transferrin- und Albuminkonjugate zytostatischer Verbindungen aus der Gruppe der Anthrazykline, Alkylantien, Antimetabolite und Cisplatin-Analoga und diese enthaltende Arzneimittel

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5843926A (ja) *	1981-09-08	1983-03-14	Suntory Ltd	選択性制癌剤
GB2116979B (en) *	1982-02-25	1985-05-15	Ward Page Faulk	Conjugates of proteins with anti-tumour agents
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
US4650675A (en) *	1983-08-18	1987-03-17	The Children's Medical Center Corporation	Oligonucleotide conjugates

1990
- 1990-07-25 CA CA002021942A patent/CA2021942C/fr not_active Expired - Lifetime
- 1990-08-09 WO PCT/CA1990/000251 patent/WO1991001757A1/fr not_active Ceased

Also Published As

Publication number	Publication date
CA2021942A1 (fr)	1991-02-11
WO1991001757A1 (fr)	1991-02-21

Legal Events

Date	Code	Title	Description
1997-07-17	EEER	Examination request
2010-07-25	MKEX	Expiry

Publication	Publication Date	Title
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ES2623017T3 (es)	2017-07-10	Procedimiento para la preparación de una formulación medicamentosa inyectable
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FI98197C (fi)	1997-05-12	Menetelmä sytotoksisten aineiden kasvainsoluihin toimittamiseen käyttökelpoisen vasta-aine-entsyymikonjugaatin valmistamiseksi
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BG63492B1 (bg)	2002-03-29	Методи за получаване на мономерни конюгати калихеамициново производно/носител
EA010508B1 (ru)	2008-10-30	Способ прицельного воздействия на определенные популяции клеток с помощью конъюгатов из майтансиноида и агента клеточного связывания, соединенных через нерасщепляемый линкер, конъюгаты и способы получения таких конъюгатов
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US5514794A (en)	1996-05-07	Antibody-drug conjugates
US4485093A (en)	1984-11-27	Immunotoxin conjugate which comprises arsanilic acid, useful for treating malignant tumors, particularly pancreatic cancer
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DE102005009084A1 (de)	2006-08-31	Proteinbindende Anthrazyklin-Peptid-Derivate und diese enthaltende Arzneimittel
HK1005018B (en)	1998-12-18	Anthracycline conjugates having a novel linker and methods for their production
US5013547A (en)	1991-05-07	Anticancer drug - antibody conjugates and method for preparing same
EP0584034A2 (fr)	1994-02-23	Conjugués de médicaments cytotoxiques pour le traitement de maladies néoplastiques
CA2021942C (fr)	2001-04-10	Couplage d'un agent anti-tumoral a un anticorps au moyen d'une glytaraldehyde preactivee
RU2106147C1 (ru)	1998-03-10	Конъюгат производного 14-бромдаунорубицина с моноклональным антителом или его фрагментом, обладающий противоопухолевой активностью и имеющий специфичность к данной опухоли, и фармацевтическая композиция, обладающая противоопухолевой активностью