DD219771A5 - Verfahren zur herstellung neuer konjugierter verbindungen von vinblastin und seinen derivaten - Google Patents

Verfahren zur herstellung neuer konjugierter verbindungen von vinblastin und seinen derivaten Download PDF

Info

Publication number: DD219771A5
Authority: DD; German Democratic Republic
Prior art keywords: vinblastine; items; protein; solution; group
Prior art date: 1983-12-29

Application number

DD84263250A

Other languages

German (de)

English (en)

Inventor

Andre B L Trouet

Kandukuri S B Rao

Jean A A Hannart

Jean-Paul De Jonghe

Original Assignee

Omnichem Sa

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.)

1983-12-29

Filing date

1984-05-22

Publication date

1985-03-13

1984-05-22 Application filed by Omnichem Sa filed Critical Omnichem Sa

1985-03-13 Publication of DD219771A5 publication Critical patent/DD219771A5/de

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 57
229960003048 vinblastine Drugs 0.000 title claims abstract description 30
JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 title claims abstract description 27
238000004519 manufacturing process Methods 0.000 title claims description 4
JXLYSJRDGCGARV-CFWMRBGOSA-N vinblastine Chemical compound C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-CFWMRBGOSA-N 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 43
102000004169 proteins and genes Human genes 0.000 claims abstract description 42
108090000623 proteins and genes Proteins 0.000 claims abstract description 42
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 claims abstract description 32
230000008569 process Effects 0.000 claims abstract description 16
150000001413 amino acids Chemical class 0.000 claims abstract description 13
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 12
150000001412 amines Chemical class 0.000 claims abstract description 8
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
239000012634 fragment Substances 0.000 claims abstract description 7
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235000018102 proteins Nutrition 0.000 claims description 40
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NDMPLJNOPCLANR-UHFFFAOYSA-N 3,4-dihydroxy-15-(4-hydroxy-18-methoxycarbonyl-5,18-seco-ibogamin-18-yl)-16-methoxy-1-methyl-6,7-didehydro-aspidospermidine-3-carboxylic acid methyl ester Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 NDMPLJNOPCLANR-UHFFFAOYSA-N 0.000 claims description 26
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 24
230000008878 coupling Effects 0.000 claims description 24
238000010168 coupling process Methods 0.000 claims description 24
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
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108010088751 Albumins Proteins 0.000 claims description 16
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235000001014 amino acid Nutrition 0.000 claims description 15
239000002904 solvent Substances 0.000 claims description 13
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-1 vinblastine compound Chemical class 0.000 claims description 10
238000009833 condensation Methods 0.000 claims description 9
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FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 5
108091006905 Human Serum Albumin Proteins 0.000 claims description 5
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NDMPLJNOPCLANR-XQLDGQACSA-N methyl (1R,9R,10S,11R,12R,19R)-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate Chemical group C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 NDMPLJNOPCLANR-XQLDGQACSA-N 0.000 claims description 4
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VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 3
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230000004048 modification Effects 0.000 claims description 3
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PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 claims description 2
125000003275 alpha amino acid group Chemical group 0.000 claims description 2
238000002523 gelfiltration Methods 0.000 claims description 2
VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 claims description 2
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CPDIYSDSKGPIFR-BQBZGAKWSA-N (2s,3s)-2-(ethylamino)-3-methylpentanoic acid Chemical compound CCN[C@H](C(O)=O)[C@@H](C)CC CPDIYSDSKGPIFR-BQBZGAKWSA-N 0.000 claims 1
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150000002894 organic compounds Chemical class 0.000 claims 1
UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 7
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125000000539 amino acid group Chemical group 0.000 abstract 1
229910052801 chlorine Inorganic materials 0.000 abstract 1
150000003254 radicals Chemical class 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 93
239000000243 solution Substances 0.000 description 82
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DABYEOZXRSTEGL-UHFFFAOYSA-N ethyl 2-amino-3-(1h-indol-3-yl)propanoate Chemical compound C1=CC=C2C(CC(N)C(=O)OCC)=CNC2=C1 DABYEOZXRSTEGL-UHFFFAOYSA-N 0.000 description 9
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125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000002372 labelling Methods 0.000 description 1
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208000032839 leukemia Diseases 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
238000011068 loading method Methods 0.000 description 1
125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229960000485 methotrexate Drugs 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000008267 milk Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000009935 nitrosation Effects 0.000 description 1
238000007034 nitrosation reaction Methods 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/04—Dimeric indole alkaloids, e.g. vincaleucoblastine
- 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
- 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
- A61K47/6805—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates the drug being a vinca alkaloid

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Immunology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD84263250A 1983-12-29 1984-05-22 Verfahren zur herstellung neuer konjugierter verbindungen von vinblastin und seinen derivaten DD219771A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
LU85161A LU85161A1 (fr)	1983-12-29	1983-12-29	Nouveaux conjugues de la vinblastine,leur procede de preparation et leur utilisation therapeutique

Publications (1)

Publication Number	Publication Date
DD219771A5 true DD219771A5 (de)	1985-03-13

Family

ID=19730204

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD84263250A DD219771A5 (de)	1983-12-29	1984-05-22	Verfahren zur herstellung neuer konjugierter verbindungen von vinblastin und seinen derivaten

Country Status (4)

Country	Link
DD (1)	DD219771A5 (fr)
IL (1)	IL71642A (fr)
LU (1)	LU85161A1 (fr)
PH (1)	PH21394A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2008098788A3 (fr) *	2007-02-16	2009-06-11	Ktb Tumorforschungs Gmbh	Récepteur et promédicament ciblé par l'antigène

1983
- 1983-12-29 LU LU85161A patent/LU85161A1/fr unknown
1984
- 1984-04-25 IL IL71642A patent/IL71642A/xx unknown
- 1984-05-22 DD DD84263250A patent/DD219771A5/de not_active IP Right Cessation
- 1984-06-06 PH PH30778A patent/PH21394A/en unknown

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2008098788A3 (fr) *	2007-02-16	2009-06-11	Ktb Tumorforschungs Gmbh	Récepteur et promédicament ciblé par l'antigène
US9216228B2 (en)	2007-02-16	2015-12-22	KTB Tumorforschungsgesellschaft MBM	Receptor and antigen targeted prodrug

Also Published As

Publication number	Publication date
PH21394A (en)	1987-10-15
LU85161A1 (fr)	1985-09-12
IL71642A (en)	1990-11-05

Legal Events

Date	Code	Title	Description
1994-11-24	ENJ	Ceased due to non-payment of renewal fee

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EP0618231B1 (fr)	1999-06-02	Conjugués immunologiquement actifs et méthode pour la préparation des-dits
DE3850306T2 (de)	1994-10-06	Camptothecin-Derivate und Verfahren zu ihrer Herstellung.
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DE68916820T2 (de)	1995-03-09	Konjugate von in Position C-3 eine Detergens-Kette enthaltenden Vinca-Derivaten.
DE69103255T2 (de)	1994-12-08	Säureempfindliche Linkermoleküle.
DE3853579T2 (de)	1995-10-05	Tri-azamakrozyklen und deren metall komplexe.
DE69325096T2 (de)	1999-09-30	Morphinderivate sowie deren konjugate und labels mit proteinen und polypeptiden
DE2808523C2 (fr)	1987-11-19
DE69329538T2 (de)	2001-06-07	Chlorophyll- und Bakteriochlorophyll-Derivate, ihre Herstellung und diese enthaltende pharmazeutische Zubereitungen
DE68917129T2 (de)	1995-03-02	Wasserlösliche antineoplastische taxolderivate.
DE3836006C2 (de)	1996-07-11	Monophosphoryllipid-A-Derivate, Verfahren zur Herstellung von Monophosphoryllipid-A-Derivaten und Verwendung von Monophosphoryllipid-A-Derivaten
DD204849A5 (de)	1983-12-14	Verfahren zur herstellung von produkten fuer die behandlung von melanomen
DE3122479A1 (de)	1982-06-16	N-(vinblastin-23-oyl)-aminosaeurederivate
EP0451810B1 (fr)	1995-08-16	Conjugés de hapten-biotin et leur usage
WO1990015798A1 (fr)	1990-12-27	Aminoalkylmaleimides et derives haptenes et antigenes issus de ceux-ci et produits conjugues avec des peptides ou des proteines
DE3879528T2 (de)	1993-08-05	Biotin-uebertraeger.
DE3000879A1 (de)	1980-07-24	Neue polyfunktionelle disulfidverbindungen
DE3025226C2 (de)	1982-07-22	Pterinderivate und ihre Verwendung zur radioimmunologischen Bestimmung von Pterinen
EP0599142A2 (fr)	1994-06-01	Méthode de fabrication d'immunoconjugués
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EP1603930B1 (fr)	2007-08-29	Derives se liant a des proteines issus de complexes de platine comprenant des ligands de cyclobutane-1,1-dicarboxylate
DD205906A5 (de)	1984-01-11	Verfahren zur herstellung von n-(vinblastinoyl-23)-derivaten von aminosaeuren
DE2739443A1 (de)	1978-03-09	Dimere indol-dihydroindolcarboxamide, verfahren zu ihrer herstellung und ihre verwendung
EP1919509B1 (fr)	2014-05-14	Reactifs hautement ramifies destines a la modification de produits biopharmaceutiques, leur production et leur utilisation
DD254009A5 (de)	1988-02-10	Verbindung zur herstellung neuer konjugierter verbindungen von vinblastin und seinen derivaten