CA2996406A1 - Piperidinobenzodiazepine compounds with anti proliferative activity - Google Patents

Piperidinobenzodiazepine compounds with anti proliferative activity Download PDF

Info

Publication number
CA2996406A1
CA2996406A1 CA2996406A CA2996406A CA2996406A1 CA 2996406 A1 CA2996406 A1 CA 2996406A1 CA 2996406 A CA2996406 A CA 2996406A CA 2996406 A CA2996406 A CA 2996406A CA 2996406 A1 CA2996406 A1 CA 2996406A1
Authority
CA
Canada
Prior art keywords
methyl
compound
cancer
alkyl
formula
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.)
Abandoned
Application number
CA2996406A
Other languages
English (en)
French (fr)
Inventor
Paul Joseph Mark JACKSON
David Edwin Thurston
Khondaker Mirazur RAHMAN
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.)
Pheon Therapeutics Ltd
Original Assignee
Femtogenix Ltd
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
Application filed by Femtogenix Ltd filed Critical Femtogenix Ltd
Publication of CA2996406A1 publication Critical patent/CA2996406A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
    • A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
    • 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
    • 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
    • A61K47/68031—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates the drug being an auristatin
    • 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
    • A61K47/68035—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates the drug being a pyrrolobenzodiazepine
    • 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
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • C07K5/0808—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Immunology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Hematology (AREA)
  • Oncology (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicinal Preparation (AREA)
  • Hydrogenated Pyridines (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA2996406A 2015-08-21 2016-08-19 Piperidinobenzodiazepine compounds with anti proliferative activity Abandoned CA2996406A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GBGB1514928.9A GB201514928D0 (en) 2015-08-21 2015-08-21 PDD compounds
GB1514928.9 2015-08-21
PCT/GB2016/052565 WO2017032983A1 (en) 2015-08-21 2016-08-19 Piperidinobenzodiazepine compounds with anti proliferative activity

Publications (1)

Publication Number Publication Date
CA2996406A1 true CA2996406A1 (en) 2017-03-02

Family

ID=54292043

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2996406A Abandoned CA2996406A1 (en) 2015-08-21 2016-08-19 Piperidinobenzodiazepine compounds with anti proliferative activity

Country Status (13)

Country Link
US (1) US10975072B2 (https=)
EP (2) EP3337795B1 (https=)
JP (2) JP6903635B2 (https=)
KR (1) KR102710425B1 (https=)
CN (2) CN108602803A (https=)
AU (1) AU2016313228B2 (https=)
CA (1) CA2996406A1 (https=)
DK (1) DK3337795T3 (https=)
EA (1) EA201890539A1 (https=)
GB (1) GB201514928D0 (https=)
IL (1) IL257650B (https=)
MX (1) MX395406B (https=)
WO (1) WO2017032983A1 (https=)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB201510010D0 (en) 2015-06-09 2015-07-22 King S College London PDD and BPD compounds
GB201514928D0 (en) * 2015-08-21 2015-10-07 King S College London PDD compounds
US20180339985A1 (en) * 2015-08-21 2018-11-29 Femtogenix Limited Pdd compounds
TW201808936A (zh) 2016-05-18 2018-03-16 美商梅爾莎納醫療公司 吡咯并苯并二氮呯類及其共軛物
CN109641910A (zh) * 2016-06-24 2019-04-16 梅尔莎纳医疗公司 吡咯并苯二氮*及其缀合物
WO2019104289A1 (en) 2017-11-27 2019-05-31 Mersana Therapeutics, Inc. Pyrrolobenzodiazepine antibody conjugates
GB201814281D0 (en) * 2018-09-03 2018-10-17 Femtogenix Ltd Cytotoxic agents
GB2597532A (en) 2020-07-28 2022-02-02 Femtogenix Ltd Cytotoxic compounds
EP4548932A1 (en) 2022-06-30 2025-05-07 Toray Industries, Inc. Pharmaceutical composition for treating and/or preventing cancer
WO2024127333A1 (en) * 2022-12-14 2024-06-20 Pheon Therapeutics Ltd Cytotoxic compounds
AU2023393382A1 (en) 2022-12-14 2025-06-19 Pheon Therapeutics Ltd Cytotoxic compounds
WO2025262641A1 (en) 2024-06-19 2025-12-26 Pheon Therapeutics Ltd Antibody drug conjugates that bind cdcp1 and uses thereof

Family Cites Families (55)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5841878A (ja) * 1981-09-07 1983-03-11 Fujisawa Pharmaceut Co Ltd ベンゾジアゼピン誘導体、その製法およびそれを有効成分として含有する抗がん剤
US4816567A (en) 1983-04-08 1989-03-28 Genentech, Inc. Recombinant immunoglobin preparations
US5366972A (en) 1989-04-20 1994-11-22 Boehringer Ingelheim Pharmaceuticals, Inc. 5,11-dihydro-6H-dipyrido(3,2-B:2',3'-E)(1,4)diazepines and their use in the prevention or treatment of HIV infection
US5418229A (en) 1990-01-06 1995-05-23 Alker; David Muscarinic receptor antagonists
WO1993013777A1 (en) 1992-01-21 1993-07-22 Merck & Co., Inc. Method of using m1-selective antimuscarinic pyridobenzodiazepinones in axial myopia therapy
EP0693070B1 (en) 1993-04-05 2002-07-24 Pharmaceutical Discovery Corporation PYRIDO[2,3-b](1,4)BENZODIAZEPINONES AS M2 RECEPTOR LIGAND FOR THE TREATMENT OF NEUROLOGICAL DISORDERS
WO1996038422A1 (en) 1995-05-31 1996-12-05 Yamanouchi Pharmaceutical Co., Ltd. Fused benzodiazepinone derivatives and medicinal composition of the same
US5650409A (en) 1995-06-02 1997-07-22 Cortex Pharmaceuticals, Inc. Benzoyl piperidines/pyrrolidines for enhancing synaptic response
US6864250B1 (en) 1997-08-22 2005-03-08 Kaken Pharmaceutical Co., Ltd. N-acylated lipophilic amino acid derivatives
DE69925133T2 (de) 1998-08-27 2006-01-19 Spirogen Ltd., Ryde Pyrrolobenzodiazepine
US6608193B2 (en) 2001-12-21 2003-08-19 The Procter & Gamble Company Methods for synthesis of amino-tetrahydroisoquinoline ring compounds
ATE361289T1 (de) 2002-08-05 2007-05-15 Lilly Co Eli Piperazinsubstituierte arylbenzodiazepine
GB0226593D0 (en) 2002-11-14 2002-12-24 Consultants Ltd Compounds
US7456169B2 (en) 2003-02-27 2008-11-25 Abbott Laboratories Inc. Heterocyclic kinase inhibitors
AU2003223107A1 (en) 2003-03-31 2004-10-25 Council Of Scentific And Industrial Research Pyrene-linked pyrrolo (2,1-c) (1,4) benzodiazepine derivatives useful as anticancer agents
GB0308335D0 (en) 2003-04-10 2003-05-14 Novartis Ag Organic compounds
GB0404578D0 (en) 2004-03-01 2004-04-07 Spirogen Ltd Pyrrolobenzodiazepines
EP1750706B1 (en) 2004-06-01 2016-10-05 University Of Virginia Patent Foundation Dual small molecule inhibitors of cancer and angiogenesis
US8466144B2 (en) 2004-07-16 2013-06-18 Proteosys Ag Muscarinic antagonists with parp and sir modulating activity as cytoprotective agents
DK1791565T3 (en) 2004-09-23 2016-08-01 Genentech Inc Cysteingensplejsede antibodies and conjugates
IT1362675B (it) 2005-03-15 2009-06-25 Menarini Internat Operations Luxembourg Sa N-idrossiammidi -sostituiti con gruppi triciclici come inibitori dell'istone deacelitasi,loro preparazione ed impiego in formulazioni farmaceutiche
US8637664B2 (en) 2005-10-05 2014-01-28 Spirogen Sarl Alkyl 4- [4- (5-oxo-2,3,5, 11a-tetrahydo-5H-pyrrolo [2, 1-c] [1,4] benzodiazepine-8-yloxy)-butyrylamino]-1H-pyrrole-2-carboxylate derivatives and related compounds for the treatment of a proliferative disease
US20090318412A1 (en) 2006-07-11 2009-12-24 Takahiro Matsumoto Tricyclic heterocyclic compound and use thereof
CA2660799C (en) * 2006-08-14 2013-03-19 Council Of Scientific & Industrial Research Pyrrolo[2,1-c][1,4]benzodiazepine hybrids and a process for the preparation thereof
CL2008001334A1 (es) 2007-05-08 2008-09-22 Genentech Inc Anticuerpo anti-muc16 disenado con cisteina; conjugado que lo comprende; metodo de produccion; formulacion farmaceutica que lo comprende; y su uso para tratar el cancer.
NZ584514A (en) 2007-10-19 2012-07-27 Genentech Inc Cysteine engineered anti-tenb2 antibodies and antibody drug conjugates
JP2009263283A (ja) 2008-04-25 2009-11-12 Toray Ind Inc Ｃ型肝炎ウイルス阻害剤
WO2009153589A1 (en) 2008-06-17 2009-12-23 Astrazeneca Ab Pyridine compounds
GB0819095D0 (en) 2008-10-17 2008-11-26 Spirogen Ltd Pyrrolobenzodiazepines
US20110263574A1 (en) 2009-01-13 2011-10-27 Proteosys Ag Pirenzepine as otoprotective agent
RU2683325C2 (ru) * 2009-02-05 2019-03-28 Иммьюноджен, Инк. Новые производные бензодиазепина
CN102482292B (zh) 2009-04-23 2017-07-18 Abbvie 公司 5‑ht受体的调节剂和其使用方法
DE102009033392A1 (de) 2009-07-16 2011-01-20 Merck Patent Gmbh Heterocyclische Verbindungen als Autotaxin-Inhibitoren II
CU20090172A7 (es) 2009-10-09 2011-10-05 Ct De Investigación Y Desarrollo De Medicamentos Sistemas tricíclicos y tetracíclicos con actividad sobre el sistema nervioso central y vascular
WO2011117882A1 (en) 2010-03-22 2011-09-29 Council Of Scientific & Industrial Research Pyrrolo[2,l-c][l,4]benzodiazepine-benzothiazole or benzoxazole conjugates linked through piperazine moiety and process for the preparation thereof
WO2012061019A2 (en) 2010-10-25 2012-05-10 Merck Sharp & Dohme Corp. Tricyclic mglur5 receptor modulators
JP5826863B2 (ja) 2011-02-15 2015-12-02 イミュノジェン・インコーポレーテッド 細胞傷害性ベンゾジアゼピン誘導体
US9006233B2 (en) 2011-04-28 2015-04-14 Uwm Research Foundation, Inc. Gabaergic receptor subtype selective ligands and their uses
ES2623042T3 (es) * 2012-04-30 2017-07-10 Medimmune Limited Pirrolobenzodiacepinas
EP3041846B1 (en) * 2013-09-02 2018-11-07 Hangzhou Dac Biotech Co., Ltd Novel cytotoxic agents for conjugation of drugs to cell binding molecule
SG11201604784XA (en) 2013-12-13 2016-07-28 Genentech Inc Anti-cd33 antibodies and immunoconjugates
GB201407816D0 (en) 2014-05-02 2014-06-18 King S College London Pyrrolobenzodiazepine Compounds
LT3191135T (lt) 2014-09-12 2020-11-25 Genentech, Inc. Anti-her2 antikūnai ir imunokonjugatai
CN107428747A (zh) 2014-11-25 2017-12-01 拜耳制药股份公司 取代的吡啶并苯并二氮杂*酮衍生物及其用途
US10508108B2 (en) 2014-12-05 2019-12-17 Merck Sharp & Dohme Corp. Tricyclic compounds as inhibitors of mutant IDH enzymes
EP3226688B1 (en) 2014-12-05 2020-07-01 Merck Sharp & Dohme Corp. Tricyclic compounds as inhibitors of mutant idh enzymes
BR112017014937A2 (pt) 2015-01-14 2018-03-13 Bristol-Myers Squibb Company dímeros de benzodiazepina ligados em ponte a heteroarileno, conjugados dos mesmos, e métodos de preparação e uso
US9504694B2 (en) 2015-03-19 2016-11-29 Cellerant Therapeutics, Inc. Isoquinolidinobenzodiazepines
GB201510010D0 (en) * 2015-06-09 2015-07-22 King S College London PDD and BPD compounds
GB201514928D0 (en) * 2015-08-21 2015-10-07 King S College London PDD compounds
EP3371191B1 (en) 2015-10-29 2020-08-26 Merck Sharp & Dohme Corp. Novel tricyclic compounds as inhibitors of mutant idh enzymes
TW201808936A (zh) 2016-05-18 2018-03-16 美商梅爾莎納醫療公司 吡咯并苯并二氮呯類及其共軛物
CN109641910A (zh) 2016-06-24 2019-04-16 梅尔莎纳医疗公司 吡咯并苯二氮*及其缀合物
WO2018053552A2 (en) 2016-09-19 2018-03-22 Cellerant Therapeutics, Inc. Isoquinolidinobenzodiazepines
US10398783B2 (en) 2016-10-20 2019-09-03 Bristol-Myers Squibb Company Antiproliferative compounds and conjugates made therefrom

Also Published As

Publication number Publication date
US20180291021A1 (en) 2018-10-11
EA201890539A1 (ru) 2018-09-28
JP2018525405A (ja) 2018-09-06
IL257650A (en) 2018-04-30
CN108602803A (zh) 2018-09-28
CN114907345A (zh) 2022-08-16
JP2021152063A (ja) 2021-09-30
EP3337795B1 (en) 2022-06-22
WO2017032983A1 (en) 2017-03-02
US10975072B2 (en) 2021-04-13
KR102710425B1 (ko) 2024-09-25
MX2018002242A (es) 2018-05-02
DK3337795T3 (da) 2022-07-25
JP6903635B2 (ja) 2021-07-14
NZ740723A (en) 2024-11-29
MX395406B (es) 2025-03-25
AU2016313228B2 (en) 2020-12-24
IL257650B (en) 2022-06-01
EP3337795A1 (en) 2018-06-27
KR20180043314A (ko) 2018-04-27
CN114907345B (zh) 2025-10-10
GB201514928D0 (en) 2015-10-07
EP4086251A1 (en) 2022-11-09
AU2016313228A1 (en) 2018-04-12

Similar Documents

Publication Publication Date Title
AU2016313228B2 (en) Piperidinobenzodiazepine compounds with anti proliferative activity
US12583857B2 (en) Anti-liferative agents comprising substituted benzo[e]pyrido[1,2-a][1,4]diazepines
JP5116686B2 (ja) Ｃｃ−１０６５類似体の調製方法及び調製用化合物
US10399970B2 (en) Pyrridinobenzodiazepine and benzopyrridodiazecine compounds
AU2010288382B2 (en) Conjugates of pyrrolo[1,4]benzodiazepine dimers as anticancer agents
ES2435779T3 (es) Agentes citotóxicos que comprenden nuevos derivados de tomaimicina y su uso terapéutico
US9999625B2 (en) Pyrrolobenzodiazepine compounds
WO2017198221A1 (zh) 嘧啶类衍生物、其制备方法和其在医药上的用途
AU2024263367A1 (en) Antibody-drug conjugate
IL313784A (en) Auristatin analogs and immune conjugates that include them
EA040562B1 (ru) Соединения пиперидинобензодиазепина, обладающие антипролиферативной активностью
WO2025181830A2 (en) Polyheterocyclic compounds as peptidyl arginine deiminase 4 (pad4) inhibitors
GB2567126A (en) PBC compounds

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20210723

FZDE Discontinued

Effective date: 20240503