WO2005082023A2 - Heterocyclic self-immolative linkers and conjugates - Google Patents
Heterocyclic self-immolative linkers and conjugates Download PDFInfo
- Publication number
- WO2005082023A2 WO2005082023A2 PCT/US2005/005960 US2005005960W WO2005082023A2 WO 2005082023 A2 WO2005082023 A2 WO 2005082023A2 US 2005005960 W US2005005960 W US 2005005960W WO 2005082023 A2 WO2005082023 A2 WO 2005082023A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- drug
- conjugate compound
- substituted
- ligand conjugate
- ligand
- 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.)
- Ceased
Links
- 0 C*C1=C(C(O*)=O)[U]C(N)=*1 Chemical compound C*C1=C(C(O*)=O)[U]C(N)=*1 0.000 description 6
- HGHWLXSFWFQDBY-UHFFFAOYSA-N CC(CC(N1CCC(C)=O)=O)C1=O Chemical compound CC(CC(N1CCC(C)=O)=O)C1=O HGHWLXSFWFQDBY-UHFFFAOYSA-N 0.000 description 1
- DEZOKKOZDXFZIK-UHFFFAOYSA-N CC(CC(N1CCOCCOCC(C)=O)=O)C1=O Chemical compound CC(CC(N1CCOCCOCC(C)=O)=O)C1=O DEZOKKOZDXFZIK-UHFFFAOYSA-N 0.000 description 1
- UOHDRHATZDNZEK-OAHLLOKOSA-N CCOC(c1c(C)nc(NC([C@@H](CCCCNC(OC(C)(C)C)=O)NC(OC(C)(C)C)=O)=O)[s]1)=O Chemical compound CCOC(c1c(C)nc(NC([C@@H](CCCCNC(OC(C)(C)C)=O)NC(OC(C)(C)C)=O)=O)[s]1)=O UOHDRHATZDNZEK-OAHLLOKOSA-N 0.000 description 1
- CMUHFUGDYMFHEI-UHFFFAOYSA-N NC(Cc(cc1)ccc1N)C(O)=O Chemical compound NC(Cc(cc1)ccc1N)C(O)=O CMUHFUGDYMFHEI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues 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
- A61K47/62—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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
- C07K5/06052—Val-amino acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Definitions
- the self-immolative linker is coupled to the ligand, through an enzymatically cleavable peptide sequence that provides a substrate for an intracellular enzyme to cleave the amide bond to initiate the self-immolative reaction.
- the self-immolative moiety in conjugates of the invention either incorporate one or more heteroatoms and thereby provides improved solubility, improves the rate of cleavage and decreases propensity for aggregation of the conjugate.
- T when T is NH, it is derived from a primary amine (-NH 2 ) pending from the drug moiety (prior to coupling to the self-immolative moiety) and when T is N, it is derived from a secondary amine (-NH-) from the drag moiety (prior to coupling to the self-immolative moiety).
- T when T is O or S, it is derived from a hydroxyl (-OH) or sulfhydryl (-SH) group respectively pending from the drag moiety prior to coupling to the self-immolative moiety.
- the reactive group of the Spacer reacts with an aldehyde, acetal, or lcetal group on a sugar (carbohydrate) of a glycosylated antibody.
- HER2 ErbB2, Genbank accession no. Ml 1730
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Medicinal Preparation (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Furan Compounds (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05714044A EP1718667B1 (en) | 2004-02-23 | 2005-02-22 | Heterocyclic self-immolative linkers and conjugates |
| JP2006554326A JP5064037B2 (ja) | 2004-02-23 | 2005-02-22 | 複素環式自壊的リンカーおよび結合体 |
| AU2005216251A AU2005216251B2 (en) | 2004-02-23 | 2005-02-22 | Heterocyclic self-immolative linkers and conjugates |
| CA2556752A CA2556752C (en) | 2004-02-23 | 2005-02-22 | Heterocyclic self-immolative linkers and conjugates |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54715204P | 2004-02-23 | 2004-02-23 | |
| US60/547,152 | 2004-02-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2005082023A2 true WO2005082023A2 (en) | 2005-09-09 |
| WO2005082023A3 WO2005082023A3 (en) | 2005-12-22 |
Family
ID=34910861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2005/005960 Ceased WO2005082023A2 (en) | 2004-02-23 | 2005-02-22 | Heterocyclic self-immolative linkers and conjugates |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US7375078B2 (https=) |
| EP (1) | EP1718667B1 (https=) |
| JP (1) | JP5064037B2 (https=) |
| AU (1) | AU2005216251B2 (https=) |
| CA (1) | CA2556752C (https=) |
| WO (1) | WO2005082023A2 (https=) |
Cited By (160)
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| WO2005099768A3 (en) * | 2004-03-23 | 2006-08-10 | Complex Biosystems Gmbh | Polymeric prodrug with a self-immolative linker |
| WO2011001052A1 (fr) | 2009-06-29 | 2011-01-06 | Sanofi-Aventis | Nouveaux conjugues, leur preparation et leur application en therapeutique |
| WO2011130613A1 (en) | 2010-04-15 | 2011-10-20 | Seattle Genetics, Inc. | Targeted pyrrolobenzodiazapine conjugates |
| WO2011130598A1 (en) | 2010-04-15 | 2011-10-20 | Spirogen Limited | Pyrrolobenzodiazepines and conjugates thereof |
| WO2011130616A1 (en) | 2010-04-15 | 2011-10-20 | Spirogen Limited | Pyrrolobenzodiazepines used to treat proliferative diseases |
| US20120322741A1 (en) * | 2010-02-25 | 2012-12-20 | Purdue Research Foundation | Psma binding ligand-linker conjugates and methods for using |
| WO2013041606A1 (en) | 2011-09-20 | 2013-03-28 | Spirogen Sàrl | Pyrrolobenzodiazepines as unsymmetrical dimeric pbd compounds for inclusion in targeted conjugates |
| WO2013055990A1 (en) | 2011-10-14 | 2013-04-18 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines and targeted conjugates |
| WO2013055993A1 (en) | 2011-10-14 | 2013-04-18 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines and targeted conjugates |
| WO2013053871A1 (en) | 2011-10-14 | 2013-04-18 | Spirogen Sàrl | Pyrrolobenzodiazepines |
| WO2013053873A1 (en) | 2011-10-14 | 2013-04-18 | Spirogen Sàrl | Pyrrolobenzodiazepines |
| WO2013177481A1 (en) | 2012-05-25 | 2013-11-28 | Immunogen, Inc. | Benzodiazepines and conjugates thereof |
| US8609105B2 (en) | 2008-03-18 | 2013-12-17 | Seattle Genetics, Inc. | Auristatin drug linker conjugates |
| WO2014057122A1 (en) | 2012-10-12 | 2014-04-17 | Adc Therapeutics Sàrl | Pyrrolobenzodiazepine-anti-cd22 antibody conjugates |
| WO2014057120A1 (en) | 2012-10-12 | 2014-04-17 | Adc Therapeutics Sàrl | Pyrrolobenzodiazepine-antibody conjugates |
| WO2014057113A1 (en) | 2012-10-12 | 2014-04-17 | Adc Therapeutics Sarl | Pyrrolobenzodiazepine - anti-psma antibody conjugates |
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| US8877897B2 (en) | 2010-02-23 | 2014-11-04 | Genentech, Inc. | Compositions and methods for the diagnosis and treatment of tumor |
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| CN104230730A (zh) * | 2009-04-03 | 2014-12-24 | 欧塞拉治疗有限公司 | L-鸟氨酸苯乙酸盐及其制备方法 |
| WO2015009740A2 (en) | 2013-07-15 | 2015-01-22 | Cell Signaling Technology, Inc. | Anti-mucin 1 binding agents and uses thereof |
| US8951528B2 (en) | 2006-02-22 | 2015-02-10 | 3M Innovative Properties Company | Immune response modifier conjugates |
| WO2015095953A1 (en) | 2013-12-27 | 2015-07-02 | The Centre For Drug Research And Development | Sulfonamide-containing linkage systems for drug conjugates |
| WO2015114171A1 (en) * | 2014-02-03 | 2015-08-06 | Eidgenoessische Technische Hochschule Zurich | Small molecule drug conjugates |
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| Publication number | Publication date |
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| US20050256030A1 (en) | 2005-11-17 |
| US20100273843A1 (en) | 2010-10-28 |
| US7375078B2 (en) | 2008-05-20 |
| AU2005216251B2 (en) | 2011-03-10 |
| US7989434B2 (en) | 2011-08-02 |
| WO2005082023A3 (en) | 2005-12-22 |
| EP1718667B1 (en) | 2013-01-09 |
| CA2556752C (en) | 2016-02-02 |
| US7754681B2 (en) | 2010-07-13 |
| JP2007527421A (ja) | 2007-09-27 |
| US20090041791A1 (en) | 2009-02-12 |
| JP5064037B2 (ja) | 2012-10-31 |
| EP1718667A4 (en) | 2009-04-08 |
| EP1718667A2 (en) | 2006-11-08 |
| AU2005216251A1 (en) | 2005-09-09 |
| CA2556752A1 (en) | 2005-09-09 |
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