CA3124935A1 - 3-(1-oxo-5-(piperidin-4-yl)isoindolin-2-yl)piperidine-2,6-dione derivatives and uses thereof - Google Patents
3-(1-oxo-5-(piperidin-4-yl)isoindolin-2-yl)piperidine-2,6-dione derivatives and uses thereof Download PDFInfo
- Publication number
- CA3124935A1 CA3124935A1 CA3124935A CA3124935A CA3124935A1 CA 3124935 A1 CA3124935 A1 CA 3124935A1 CA 3124935 A CA3124935 A CA 3124935A CA 3124935 A CA3124935 A CA 3124935A CA 3124935 A1 CA3124935 A1 CA 3124935A1
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- Prior art keywords
- alkyl
- optionally substituted
- heteroatoms selected
- cycloalkyl
- halogen
- Prior art date
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- CIBYAIJUOIICFR-UHFFFAOYSA-N 3-[3-oxo-6-[1-(pyrimidin-4-ylmethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1=NC=NC=C1)C1C(NC(CC1)=O)=O CIBYAIJUOIICFR-UHFFFAOYSA-N 0.000 claims 1
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- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- GKTQKQTXHNUFSP-UHFFFAOYSA-N thieno[3,4-c]pyrrole-4,6-dione Chemical compound S1C=C2C(=O)NC(=O)C2=C1 GKTQKQTXHNUFSP-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 208000013818 thyroid gland medullary carcinoma Diseases 0.000 description 1
- 208000030045 thyroid gland papillary carcinoma Diseases 0.000 description 1
- 201000006134 tongue cancer Diseases 0.000 description 1
- 208000025358 tongue carcinoma Diseases 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 208000017997 tumor of parathyroid gland Diseases 0.000 description 1
- 208000010570 urinary bladder carcinoma Diseases 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
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- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US201962806140P | 2019-02-15 | 2019-02-15 | |
| US62/806,140 | 2019-02-15 | ||
| PCT/IB2020/051205 WO2020165833A1 (en) | 2019-02-15 | 2020-02-13 | 3-(1-oxo-5-(piperidin-4-yl)isoindolin-2-yl)piperidine-2,6-dione derivatives and uses thereof |
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| CA3124935A1 true CA3124935A1 (en) | 2020-08-20 |
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| EP (1) | EP3924054B1 (OSRAM) |
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| BR (1) | BR112021015783A2 (OSRAM) |
| CA (1) | CA3124935A1 (OSRAM) |
| EA (1) | EA202192019A1 (OSRAM) |
| ES (1) | ES3032659T3 (OSRAM) |
| MX (1) | MX2021009763A (OSRAM) |
| WO (1) | WO2020165833A1 (OSRAM) |
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| SG11202113129UA (en) | 2019-05-31 | 2021-12-30 | Ikena Oncology Inc | Tead inhibitors and uses thereof |
| CA3141826A1 (en) | 2019-05-31 | 2020-12-03 | Ikena Oncology, Inc. | Tead inhibitors and uses thereof |
| AU2020374957A1 (en) * | 2019-10-30 | 2022-04-28 | Dana-Farber Cancer Institute, Inc. | Small molecule degraders of Helios and methods of use |
| WO2022081925A1 (en) * | 2020-10-14 | 2022-04-21 | C4 Therapeutics, Inc. | Tricyclic ligands for degradation of ikzf2 or ikzf4 |
| MX2023004149A (es) * | 2020-10-16 | 2023-07-10 | Dana Farber Cancer Inst Inc | Degradadores de moléculas pequeñas de piperidinilo de helios y procedimientos de uso. |
| CN116669769A (zh) * | 2020-10-16 | 2023-08-29 | 达纳-法伯癌症研究所公司 | Helios的哌啶基小分子降解剂和使用方法 |
| WO2022120355A1 (en) * | 2020-12-02 | 2022-06-09 | Ikena Oncology, Inc. | Tead degraders and uses thereof |
| IL307343A (en) * | 2021-04-06 | 2023-11-01 | Bristol Myers Squibb Co | Pyridinyl substituted oxisoisoindoline compounds |
| AU2022265693A1 (en) * | 2021-04-29 | 2023-09-07 | Dana-Farber Cancer Institute, Inc. | Phthalimido cereblon complex binders and transcription factor degraders and methods of use |
| US20240239785A1 (en) * | 2021-04-29 | 2024-07-18 | Neomorph, Inc. | Substituted 2-(2,6-dioxopiperidin-3-yl)-5-(1-piperidin-4-yl)isoindoline-1,3-dione derivatives and uses thereof |
| AU2022306297A1 (en) | 2021-07-09 | 2024-02-08 | Plexium, Inc. | Aryl compounds and pharmaceutical compositions that modulate ikzf2 |
| KR20240110576A (ko) * | 2021-10-22 | 2024-07-15 | 글루탁스 테라퓨틱스 (상하이) 씨오., 엘티디. | Crbn e3 리가제 리간드 화합물, 리간드 화합물에 기초하여 개발된 단백질 분해제 및 이들의 응용 |
| WO2023122615A1 (en) * | 2021-12-22 | 2023-06-29 | Gilead Sciences, Inc. | Ikaros zinc finger family degraders and uses thereof |
| CN116640122A (zh) * | 2022-02-16 | 2023-08-25 | 苏州国匡医药科技有限公司 | Ikzf2降解剂及包含其的药物组合物和用途 |
| TW202346277A (zh) | 2022-03-17 | 2023-12-01 | 美商基利科學股份有限公司 | Ikaros鋅指家族降解劑及其用途 |
| WO2024064358A1 (en) | 2022-09-23 | 2024-03-28 | Ifm Due, Inc. | Compounds and compositions for treating conditions associated with sting activity |
| WO2024096753A1 (en) * | 2022-11-02 | 2024-05-10 | Captor Therapeutics S.A. | Nek7 degraders and methods of use thereof |
| WO2024173646A1 (en) * | 2023-02-16 | 2024-08-22 | Innovo Therapeutics, Inc. | Cyclin-dependent kinase degrading compounds |
| WO2025067466A1 (zh) * | 2023-09-28 | 2025-04-03 | 杭州多域生物技术有限公司 | 一种杂环化合物、其组合物及应用 |
| WO2025097090A1 (en) * | 2023-11-02 | 2025-05-08 | Neomorph, Inc. | Substituted (piperidin-4-yl)-1,5-naphthyridine and (piperidin-4-yl)quinoline derivatives and uses thereof |
Family Cites Families (362)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2779780A (en) | 1955-03-01 | 1957-01-29 | Du Pont | 1, 4-diamino-2, 3-dicyano-1, 4-bis (substituted mercapto) butadienes and their preparation |
| US4261989A (en) | 1979-02-19 | 1981-04-14 | Kaken Chemical Co. Ltd. | Geldanamycin derivatives and antitumor drug |
| US4433059A (en) | 1981-09-08 | 1984-02-21 | Ortho Diagnostic Systems Inc. | Double antibody conjugate |
| US4444878A (en) | 1981-12-21 | 1984-04-24 | Boston Biomedical Research Institute, Inc. | Bispecific antibody determinants |
| US4851332A (en) | 1985-04-01 | 1989-07-25 | Sloan-Kettering Institute For Cancer Research | Choriocarcinoma monoclonal antibodies and antibody panels |
| US5869620A (en) | 1986-09-02 | 1999-02-09 | Enzon, Inc. | Multivalent antigen-binding proteins |
| US5114946A (en) | 1987-06-12 | 1992-05-19 | American Cyanamid Company | Transdermal delivery of pharmaceuticals |
| US4818541A (en) | 1987-08-19 | 1989-04-04 | Schering Corporation | Transdermal delivery of enantiomers of phenylpropanolamine |
| JPH021556A (ja) | 1988-06-09 | 1990-01-05 | Snow Brand Milk Prod Co Ltd | ハイブリッド抗体及びその作製方法 |
| DE3920358A1 (de) | 1989-06-22 | 1991-01-17 | Behringwerke Ag | Bispezifische und oligospezifische, mono- und oligovalente antikoerperkonstrukte, ihre herstellung und verwendung |
| AU6290090A (en) | 1989-08-29 | 1991-04-08 | University Of Southampton | Bi-or trispecific (fab)3 or (fab)4 conjugates |
| US5273743A (en) | 1990-03-09 | 1993-12-28 | Hybritech Incorporated | Trifunctional antibody-like compounds as a combined diagnostic and therapeutic agent |
| GB9012995D0 (en) | 1990-06-11 | 1990-08-01 | Celltech Ltd | Multivalent antigen-binding proteins |
| US5582996A (en) | 1990-12-04 | 1996-12-10 | The Wistar Institute Of Anatomy & Biology | Bifunctional antibodies and method of preparing same |
| DE4118120A1 (de) | 1991-06-03 | 1992-12-10 | Behringwerke Ag | Tetravalente bispezifische rezeptoren, ihre herstellung und verwendung |
| US6511663B1 (en) | 1991-06-11 | 2003-01-28 | Celltech R&D Limited | Tri- and tetra-valent monospecific antigen-binding proteins |
| US5637481A (en) | 1993-02-01 | 1997-06-10 | Bristol-Myers Squibb Company | Expression vectors encoding bispecific fusion proteins and methods of producing biologically active bispecific fusion proteins in a mammalian cell |
| CA2078539C (en) | 1991-09-18 | 2005-08-02 | Kenya Shitara | Process for producing humanized chimera antibody |
| US5932448A (en) | 1991-11-29 | 1999-08-03 | Protein Design Labs., Inc. | Bispecific antibody heterodimers |
| EP0654085B1 (en) | 1992-01-23 | 1997-04-02 | MERCK PATENT GmbH | Monomeric and dimeric antibody-fragment fusion proteins |
| DE69334255D1 (de) | 1992-02-06 | 2009-02-12 | Novartis Vaccines & Diagnostic | Marker für Krebs und biosynthetisches Bindeprotein dafür |
| US5646253A (en) | 1994-03-08 | 1997-07-08 | Memorial Sloan-Kettering Cancer Center | Recombinant human anti-LK26 antibodies |
| AU675223B2 (en) | 1992-05-08 | 1997-01-30 | Creative Biomolecules, Inc. | Chimeric multivalent protein analogues and methods of use thereof |
| US6005079A (en) | 1992-08-21 | 1999-12-21 | Vrije Universiteit Brussels | Immunoglobulins devoid of light chains |
| EP0672068A4 (en) | 1992-09-25 | 1997-02-26 | Commw Scient Ind Res Org | TARGET MOLECULES BINDING POLYPEPTIDES. |
| GB9221657D0 (en) | 1992-10-15 | 1992-11-25 | Scotgen Ltd | Recombinant bispecific antibodies |
| US5262564A (en) | 1992-10-30 | 1993-11-16 | Octamer, Inc. | Sulfinic acid adducts of organo nitroso compounds useful as retroviral inactivating agents anti-retroviral agents and anti-tumor agents |
| EP0627932B1 (en) | 1992-11-04 | 2002-05-08 | City Of Hope | Antibody construct |
| GB9323648D0 (en) | 1992-11-23 | 1994-01-05 | Zeneca Ltd | Proteins |
| DK0672142T3 (da) | 1992-12-04 | 2001-06-18 | Medical Res Council | Multivalente og multispecifikke bindingsproteiner samt fremstilling og anvendelse af disse |
| US6476198B1 (en) | 1993-07-13 | 2002-11-05 | The Scripps Research Institute | Multispecific and multivalent antigen-binding polypeptide molecules |
| US5635602A (en) | 1993-08-13 | 1997-06-03 | The Regents Of The University Of California | Design and synthesis of bispecific DNA-antibody conjugates |
| WO1995009917A1 (en) | 1993-10-07 | 1995-04-13 | The Regents Of The University Of California | Genetically engineered bispecific tetravalent antibodies |
| AU7863794A (en) | 1993-11-16 | 1995-06-06 | Pola Chemical Industries Inc. | Antihuman tyrosinase monoclonal antibody |
| US5635388A (en) | 1994-04-04 | 1997-06-03 | Genentech, Inc. | Agonist antibodies against the flk2/flt3 receptor and uses thereof |
| EP0756604A1 (en) | 1994-04-22 | 1997-02-05 | THE UNITED STATES OF AMERICA, as represented by the Secretary of the Department of Health and Human Services | Melanoma antigens |
| US5786464C1 (en) | 1994-09-19 | 2012-04-24 | Gen Hospital Corp | Overexpression of mammalian and viral proteins |
| EP0787185A2 (en) | 1994-10-20 | 1997-08-06 | MorphoSys AG | Targeted hetero-association of recombinant proteins to multi-functional complexes |
| ATE186745T1 (de) | 1995-01-18 | 1999-12-15 | Roche Diagnostics Gmbh | Antikörper gegen cd30, die proteolytische spaltung und abgabe des membrangebundenen cd30 antigens verhindern |
| US5731168A (en) | 1995-03-01 | 1998-03-24 | Genentech, Inc. | Method for making heteromultimeric polypeptides |
| DE69633175T2 (de) | 1995-05-23 | 2005-08-11 | Morphosys Ag | Multimere proteine |
| US5989830A (en) | 1995-10-16 | 1999-11-23 | Unilever Patent Holdings Bv | Bifunctional or bivalent antibody fragment analogue |
| AU703769B2 (en) | 1996-01-05 | 1999-04-01 | Government Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services, The | Mesothelium antigen and methods and kits for targeting it |
| DE19608769C1 (de) | 1996-03-07 | 1997-04-10 | Univ Eberhard Karls | Antikörper BV10A4H2 |
| DE69730209T2 (de) | 1996-04-04 | 2005-04-14 | Unilever N.V. | Multivalentes und multispezifisches Antigenbindungsprotein |
| US6114148C1 (en) | 1996-09-20 | 2012-05-01 | Gen Hospital Corp | High level expression of proteins |
| US6365712B1 (en) | 1996-10-25 | 2002-04-02 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Methods and compositions for inhibiting inflammation and angiogenesis comprising a mammalian CD97 α subunit |
| WO1998049198A1 (en) | 1997-04-30 | 1998-11-05 | Enzon, Inc. | Single-chain antigen-binding proteins capable of glycosylation, production and uses thereof |
| US20030207346A1 (en) | 1997-05-02 | 2003-11-06 | William R. Arathoon | Method for making multispecific antibodies having heteromultimeric and common components |
| US20020062010A1 (en) | 1997-05-02 | 2002-05-23 | Genentech, Inc. | Method for making multispecific antibodies having heteromultimeric and common components |
| ES2231991T3 (es) | 1997-06-11 | 2005-05-16 | Borean Pharma A/S | Modulo de trimerizacion. |
| BR9813276A (pt) | 1997-10-27 | 2000-08-22 | Unilever Nv | Proteìna multivalente de ligação de antìgeno, sequências de nucleotìdeos, vetor de expressão, célula hospedeira, processo para preparação de proteìna multivalente de ligação de antìgeno, e, uso da mesma |
| EP1025230B1 (en) | 1997-12-01 | 2006-02-08 | THE GOVERNMENT OF THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES | ANTIBODIES, INCLUDING Fv MOLECULES, AND IMMUNOCONJUGATES HAVING HIGH BINDING AFFINITY FOR MESOTHELIN AND METHODS FOR THEIR USE |
| ATE283364T1 (de) | 1998-01-23 | 2004-12-15 | Vlaams Interuniv Inst Biotech | Mehrzweck-antikörperderivate |
| CZ121599A3 (cs) | 1998-04-09 | 1999-10-13 | Aventis Pharma Deutschland Gmbh | Jednořetězcová molekula vázající několik antigenů, způsob její přípravy a léčivo obsahující tuto molekulu |
| DE19819846B4 (de) | 1998-05-05 | 2016-11-24 | Deutsches Krebsforschungszentrum Stiftung des öffentlichen Rechts | Multivalente Antikörper-Konstrukte |
| GB9812545D0 (en) | 1998-06-10 | 1998-08-05 | Celltech Therapeutics Ltd | Biological products |
| US6803448B1 (en) | 1998-07-22 | 2004-10-12 | Vanderbilt University | GBS toxin receptor |
| DK1100830T3 (da) | 1998-07-28 | 2004-01-19 | Micromet Ag | Heterominiantistoffer |
| US6333396B1 (en) | 1998-10-20 | 2001-12-25 | Enzon, Inc. | Method for targeted delivery of nucleic acids |
| IL143236A0 (en) | 1998-12-16 | 2002-04-21 | Warner Lambert Co | Treatment of arthritis with mek inhibitors |
| US6528481B1 (en) | 1999-02-16 | 2003-03-04 | The Burnam Institute | NG2/HM proteoglycan-binding peptides that home to angiogenic vasculature and related methods |
| US7534866B2 (en) | 2005-10-19 | 2009-05-19 | Ibc Pharmaceuticals, Inc. | Methods and compositions for generating bioactive assemblies of increased complexity and uses |
| US7527787B2 (en) | 2005-10-19 | 2009-05-05 | Ibc Pharmaceuticals, Inc. | Multivalent immunoglobulin-based bioactive assemblies |
| JP4787439B2 (ja) | 1999-08-17 | 2011-10-05 | バイオジェン・アイデック・エムエイ・インコーポレイテッド | 免疫調節因子であるbaffレセプター(bcma) |
| DE60038252T2 (de) | 1999-09-30 | 2009-03-19 | Kyowa Hakko Kogyo Co., Ltd. | Menschlicher Antikörper gegen Gangliosid GD3 für die Transplantationskomplentarität bestimmende Region und Derivate des Antikörpers gegen das Gangliosid GD3 |
| EP1235847B1 (en) | 1999-11-29 | 2016-01-20 | The Trustees of Columbia University in the City of New York | ISOLATION OF FIVE NOVEL GENES CODING FOR NEW Fc RECEPTORS-TYPE MELANOMA INVOLVED IN THE PATHOGENESIS OF LYMPHOMA/MELANOMA |
| PT1234031T (pt) | 1999-11-30 | 2017-06-26 | Mayo Foundation | B7-h1, uma nova molécula imunoregulatória |
| GB0000313D0 (en) | 2000-01-10 | 2000-03-01 | Astrazeneca Uk Ltd | Formulation |
| US20040002068A1 (en) | 2000-03-01 | 2004-01-01 | Corixa Corporation | Compositions and methods for the detection, diagnosis and therapy of hematological malignancies |
| ATE510855T1 (de) | 2000-03-06 | 2011-06-15 | Univ Kentucky Res Found | Verwendung eines antikörpers oder eines immunotoxins, der bzw. das selektiv an cd123 bindet zur beeinträchtigung hämatologischer krebs-vorläuferzellen |
| MXPA02010011A (es) | 2000-04-11 | 2003-04-25 | Genentech Inc | Anticuerpos multivalentes y usos para los mismos. |
| WO2001090192A2 (en) | 2000-05-24 | 2001-11-29 | Imclone Systems Incorporated | Bispecific immunoglobulin-like antigen binding proteins and method of production |
| EP1294904A1 (en) | 2000-06-30 | 2003-03-26 | Vlaams Interuniversitair Instituut voor Biotechnologie vzw. | Heterodimeric fusion proteins |
| DZ3401A1 (fr) | 2000-07-19 | 2002-01-24 | Warner Lambert Co | Esters oxygenes d'acides 4-iodophenylamino benzhydroxamiques |
| WO2002008293A2 (en) | 2000-07-25 | 2002-01-31 | Immunomedics Inc. | Multivalent target binding protein |
| GB0020685D0 (en) | 2000-08-22 | 2000-10-11 | Novartis Ag | Organic compounds |
| US7718600B2 (en) | 2000-09-29 | 2010-05-18 | The Trustees Of Princeton University | IAP binding compounds |
| KR100870123B1 (ko) | 2000-10-20 | 2008-11-25 | 츄가이 세이야꾸 가부시키가이샤 | 저분자화 아고니스트 항체 |
| US7090843B1 (en) | 2000-11-28 | 2006-08-15 | Seattle Genetics, Inc. | Recombinant anti-CD30 antibodies and uses thereof |
| US6995162B2 (en) | 2001-01-12 | 2006-02-07 | Amgen Inc. | Substituted alkylamine derivatives and methods of use |
| US7829084B2 (en) | 2001-01-17 | 2010-11-09 | Trubion Pharmaceuticals, Inc. | Binding constructs and methods for use thereof |
| AU2002247826A1 (en) | 2001-03-13 | 2002-09-24 | University College London | Specific binding members |
| CN1294148C (zh) | 2001-04-11 | 2007-01-10 | 中国科学院遗传与发育生物学研究所 | 环状单链三特异抗体 |
| US6770622B2 (en) | 2001-06-08 | 2004-08-03 | Gary A. Jarvis | N-terminally truncated galectin-3 for use in treating cancer |
| WO2003002609A2 (en) | 2001-06-28 | 2003-01-09 | Domantis Limited | Dual-specific ligand and its use |
| US6833441B2 (en) | 2001-08-01 | 2004-12-21 | Abmaxis, Inc. | Compositions and methods for generating chimeric heteromultimers |
| EP2383290B1 (en) | 2001-08-23 | 2019-05-08 | Rsr Limited | Epitope regions of a thyrotropin (tsh) receptor, uses thereof and antibodies thereto |
| DE60124912T2 (de) | 2001-09-14 | 2007-06-14 | Affimed Therapeutics Ag | Multimerische, einzelkettige, Tandem-Fv-Antikörper |
| JP4716350B2 (ja) | 2001-12-04 | 2011-07-06 | ダナ−ファーバー キャンサー インスティテュート インク. | 潜伏期膜タンパク質に対する抗体およびそれらの使用 |
| WO2003049684A2 (en) | 2001-12-07 | 2003-06-19 | Centocor, Inc. | Pseudo-antibody constructs |
| KR100956195B1 (ko) | 2002-02-01 | 2010-05-06 | 어리어드 파마슈티칼스, 인코포레이티드 | 인 함유 화합물 및 이의 용도 |
| AU2003209446B2 (en) | 2002-03-01 | 2008-09-25 | Immunomedics, Inc. | Bispecific antibody point mutations for enhancing rate of clearance |
| CN104876904A (zh) | 2002-03-08 | 2015-09-02 | 卫材R&D管理株式会社 | 用作医药品的大环化合物 |
| TWI338685B (en) | 2002-03-13 | 2011-03-11 | Array Biopharma Inc | N3 alkylated benzimid azole derivatives as mek inhibitors |
| WO2003087163A1 (en) | 2002-04-15 | 2003-10-23 | Chugai Seiyaku Kabushiki Kaisha | METHOD OF CONSTRUCTING scDb LIBRARY |
| TWI275390B (en) | 2002-04-30 | 2007-03-11 | Wyeth Corp | Process for the preparation of 7-substituted-3- quinolinecarbonitriles |
| US7446190B2 (en) | 2002-05-28 | 2008-11-04 | Sloan-Kettering Institute For Cancer Research | Nucleic acids encoding chimeric T cell receptors |
| EP1537878B1 (en) | 2002-07-03 | 2010-09-22 | Ono Pharmaceutical Co., Ltd. | Immunopotentiating compositions |
| GB0215823D0 (en) | 2002-07-09 | 2002-08-14 | Astrazeneca Ab | Quinazoline derivatives |
| CA2505994A1 (en) | 2002-11-15 | 2004-06-03 | Chiron Corporation | Methods for preventing and treating cancer metastasis and bone loss associated with cancer metastasis |
| DE50306067D1 (de) | 2002-11-26 | 2007-02-01 | Brahms Ag | Nachweis von tsh-rezeptor-autoantikörpern mit affinitätsgereinigten antikörpern |
| WO2004056875A1 (en) | 2002-12-23 | 2004-07-08 | Wyeth | Antibodies against pd-1 and uses therefor |
| AU2003292625B2 (en) | 2002-12-26 | 2008-07-24 | Eisai R & D Management Co., Ltd. | Selective estrogen receptor modulators |
| GB0230203D0 (en) | 2002-12-27 | 2003-02-05 | Domantis Ltd | Fc fusion |
| GB0305702D0 (en) | 2003-03-12 | 2003-04-16 | Univ Birmingham | Bispecific antibodies |
| WO2004087758A2 (en) | 2003-03-26 | 2004-10-14 | Neopharm, Inc. | Il 13 receptor alpha 2 antibody and methods of use |
| US20050003403A1 (en) | 2003-04-22 | 2005-01-06 | Rossi Edmund A. | Polyvalent protein complex |
| CU23403A1 (es) | 2003-04-23 | 2009-08-04 | Centro Inmunologia Molecular | Anticuerpos recombinantes y fragmentos que reconocen el gangliósido n-glicolil gm3 y su uso para diagnóstico y tratamiento de tumores |
| CA2529945A1 (en) | 2003-06-27 | 2005-01-06 | Biogen Idec Ma Inc. | Use of hydrophobic-interaction-chromatography or hinge-region modifications for the production of homogeneous antibody-solutions |
| CN1833020A (zh) | 2003-06-27 | 2006-09-13 | 迪亚德克瑟斯公司 | Pro104抗体组合物及其使用方法 |
| EP1638510B1 (en) | 2003-07-01 | 2015-09-02 | Immunomedics, Inc. | Multivalent carriers of bi-specific antibodies |
| US7696322B2 (en) | 2003-07-28 | 2010-04-13 | Catalent Pharma Solutions, Inc. | Fusion antibodies |
| JP2007525971A (ja) | 2003-08-05 | 2007-09-13 | モルフォテック、インク. | 癌に関連する変異体細胞表面分子 |
| US7399865B2 (en) | 2003-09-15 | 2008-07-15 | Wyeth | Protein tyrosine kinase enzyme inhibitors |
| CA2542046A1 (en) | 2003-10-08 | 2005-04-21 | Kyowa Hakko Kogyo Co., Ltd. | Fused protein composition |
| JPWO2005035577A1 (ja) | 2003-10-08 | 2007-11-22 | 協和醗酵工業株式会社 | ガングリオシドgd3に特異的に結合する抗体組成物 |
| US7435596B2 (en) | 2004-11-04 | 2008-10-14 | St. Jude Children's Research Hospital, Inc. | Modified cell line and method for expansion of NK cell |
| WO2005062916A2 (en) | 2003-12-22 | 2005-07-14 | Centocor, Inc. | Methods for generating multimeric molecules |
| GB0329825D0 (en) | 2003-12-23 | 2004-01-28 | Celltech R&D Ltd | Biological products |
| US20050266425A1 (en) | 2003-12-31 | 2005-12-01 | Vaccinex, Inc. | Methods for producing and identifying multispecific antibodies |
| PT2311873T (pt) | 2004-01-07 | 2018-11-20 | Novartis Vaccines & Diagnostics Inc | Anticorpo monoclonal específico para m-csf e respetivos usos |
| US20100093645A1 (en) | 2004-01-16 | 2010-04-15 | Shaomeng Wang | SMAC Peptidomimetics and the Uses Thereof |
| CA2553874A1 (en) | 2004-01-16 | 2005-08-04 | The Regents Of The University Of Michigan | Conformationally constrained smac mimetics and the uses thereof |
| US8383575B2 (en) | 2004-01-30 | 2013-02-26 | Paul Scherrer Institut | (DI)barnase-barstar complexes |
| SI2511297T1 (sl) | 2004-02-06 | 2015-07-31 | Morphosys Ag | Proti -CD38 humana protitelesa in njihova uporaba |
| EP1740173A4 (en) | 2004-03-23 | 2009-05-27 | Genentech Inc | AZABICYCLOOCTAN IAP INHIBITORS |
| RS52545B (sr) | 2004-04-07 | 2013-04-30 | Novartis Ag | Inhibitori protein apoptoze (iap) |
| BRPI0510883B8 (pt) | 2004-06-01 | 2021-05-25 | Genentech Inc | composto conjugado de droga e anticorpo, composição farmacêutica, método de fabricação de composto conjugado de droga e anticorpo e usos de uma formulação, de um conjugado de droga e anticorpo e um agente quimioterapêutico e de uma combinação |
| MXPA06014478A (es) | 2004-06-11 | 2007-03-21 | Japan Tobacco Inc | Derivados de 5-amino-2, 4, 7-trioxo-3, 4, 7, 8-tetrahidro -2h-pirido[2, 3-d]pirimidina y compuestos relacionados para el tratamiento del cancer. |
| PT1778718E (pt) | 2004-07-02 | 2014-12-03 | Genentech Inc | Inibidores de iap |
| WO2006010118A2 (en) | 2004-07-09 | 2006-01-26 | The Regents Of The University Of Michigan | Conformationally constrained smac mimetics and the uses thereof |
| EA200700225A1 (ru) | 2004-07-12 | 2008-02-28 | Айдан Фармасьютикалз, Инк. | Аналоги тетрапептида |
| AU2005274937B2 (en) | 2004-07-15 | 2011-08-18 | Medivir Ab | IAP binding compounds |
| EP1786918A4 (en) | 2004-07-17 | 2009-02-11 | Imclone Systems Inc | NEW BISPECIFIC ANTIBODY TETRAVALENT |
| AU2005282700A1 (en) | 2004-09-02 | 2006-03-16 | Genentech, Inc. | Heteromultimeric molecules |
| WO2006039238A2 (en) | 2004-09-30 | 2006-04-13 | The Goverment Of The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Irta2 antibodies and methods of use |
| PT1802291E (pt) | 2004-10-04 | 2012-03-12 | Univ Minnesota | Miméticos conformacionais de péptidos à base de calixareno, métodos de utilização e métodos de preparação |
| KR20120127754A (ko) | 2004-12-20 | 2012-11-23 | 제넨테크, 인크. | Iap의 피롤리딘 억제제 |
| MY146381A (en) | 2004-12-22 | 2012-08-15 | Amgen Inc | Compositions and methods relating relating to anti-igf-1 receptor antibodies |
| US20080247944A1 (en) | 2005-01-12 | 2008-10-09 | Robert Graziano | Irta-2 Antibodies and Their Uses |
| EP1850873B1 (en) | 2005-02-08 | 2018-11-28 | Genzyme Corporation | Antibodies to tgfbeta |
| AU2006223301B2 (en) | 2005-03-10 | 2010-11-04 | Eisai, Inc. | Anti-mesothelin antibodies |
| EP1866339B8 (en) | 2005-03-25 | 2021-12-01 | GITR, Inc. | Gitr binding molecules and uses therefor |
| EP3050963B1 (en) | 2005-03-31 | 2019-09-18 | Chugai Seiyaku Kabushiki Kaisha | Process for production of polypeptide by regulation of assembly |
| CA2604032C (en) | 2005-04-06 | 2017-08-22 | Ibc Pharmaceuticals, Inc. | Methods for generating stably linked complexes composed of homodimers, homotetramers or dimers of dimers and uses |
| CA2605024C (en) | 2005-04-15 | 2018-05-22 | Macrogenics, Inc. | Covalent diabodies and uses thereof |
| EP2418278A3 (en) | 2005-05-09 | 2012-07-04 | Ono Pharmaceutical Co., Ltd. | Human monoclonal antibodies to programmed death 1(PD-1) and methods for treating cancer using anti-PD-1 antibodies alone or in combination with other immunotherapeutics |
| US20060263367A1 (en) | 2005-05-23 | 2006-11-23 | Fey Georg H | Bispecific antibody devoid of Fc region and method of treatment using same |
| EP1726650A1 (en) | 2005-05-27 | 2006-11-29 | Universitätsklinikum Freiburg | Monoclonal antibodies and single chain antibody fragments against cell-surface prostate specific membrane antigen |
| KR20080019249A (ko) | 2005-06-15 | 2008-03-03 | 쉐링 코포레이션 | 안정한 항체 제형 |
| KR101607288B1 (ko) | 2005-07-01 | 2016-04-05 | 이. 알. 스퀴부 앤드 선즈, 엘.엘.씨. | 예정 사멸 리간드 1 (피디-엘1)에 대한 인간 모노클로날 항체 |
| JP4557003B2 (ja) | 2005-07-01 | 2010-10-06 | 株式会社村田製作所 | 多層セラミック基板およびその製造方法ならびに多層セラミック基板作製用複合グリーンシート |
| TWI424147B (zh) | 2005-07-04 | 2014-01-21 | 尼康美景股份有限公司 | Distance measuring device |
| CA2618218C (en) | 2005-07-21 | 2015-06-30 | Ardea Biosciences, Inc. | N-(arylamino)-sulfonamide inhibitors of mek |
| EP2520588A1 (en) | 2005-08-19 | 2012-11-07 | Abbott Laboratories | Dual variable domain immunoglobulin and uses thereof |
| US7612181B2 (en) | 2005-08-19 | 2009-11-03 | Abbott Laboratories | Dual variable domain immunoglobulin and uses thereof |
| ATE452913T1 (de) | 2005-08-26 | 2010-01-15 | Pls Design Gmbh | Bivalente igy antikörperkonstrukte für diagnostische und therapeutische anwendungen |
| WO2007044887A2 (en) | 2005-10-11 | 2007-04-19 | Transtarget, Inc. | Method for producing a population of homogenous tetravalent bispecific antibodies |
| EP1962961B1 (en) | 2005-11-29 | 2013-01-09 | The University Of Sydney | Demibodies: dimerisation-activated therapeutic agents |
| HRP20120701T1 (hr) | 2005-12-08 | 2012-10-31 | Medarex, Inc. | Humana monoklonska protutijela protiv fukozil-gm1 i postupci za uporabu antifukozil-gm1 |
| EP1806365A1 (en) | 2006-01-05 | 2007-07-11 | Boehringer Ingelheim International GmbH | Antibody molecules specific for fibroblast activation protein and immunoconjugates containing them |
| US9303080B2 (en) | 2006-01-13 | 2016-04-05 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services, National Institutes Of Health | Codon optimized IL-15 and IL-15R-alpha genes for expression in mammalian cells |
| JP2009526857A (ja) | 2006-02-15 | 2009-07-23 | イムクローン・リミテッド・ライアビリティ・カンパニー | 機能性抗体 |
| AU2007227292B2 (en) | 2006-03-17 | 2012-04-12 | Biogen Ma Inc. | Stabilized polypeptide compositions |
| ES2363891T3 (es) | 2006-03-20 | 2011-08-18 | The Regents Of The University Of California | Anticuerpos contra el antígeno de células troncales de la próstata (psca) modificados genéticamente para el direccionamiento al cáncer. |
| CA2646965C (en) | 2006-03-24 | 2016-06-21 | Jonathan H. Davis | Engineered heterodimeric protein domains |
| US8946391B2 (en) | 2006-03-24 | 2015-02-03 | The Regents Of The University Of California | Construction of a multivalent scFv through alkyne-azide 1,3-dipolar cycloaddition |
| JP5165672B2 (ja) | 2006-03-29 | 2013-03-21 | キングス カレッジ ロンドン | Tshrに対するアゴニスト抗体 |
| CN105177091A (zh) | 2006-03-31 | 2015-12-23 | 中外制药株式会社 | 用于纯化双特异性抗体的抗体修饰方法 |
| RS56600B1 (sr) | 2006-04-19 | 2018-02-28 | Novartis Ag | 6-o-supstituisana jedinjenja benzoksazola i benzotiazola i postupci inhibicije csf-1r signalinga |
| TWI395754B (zh) | 2006-04-24 | 2013-05-11 | Amgen Inc | 人類化之c-kit抗體 |
| PT2016102E (pt) | 2006-05-03 | 2012-05-15 | Us Gov Health & Human Serv | Recetores de célula t quimérica e materiais relacionados e métodos de uso |
| WO2008011216A2 (en) | 2006-05-16 | 2008-01-24 | Pro-Pharmaceuticals, Inc. | Galactose-pronged polysaccharides in a formulation for antifibrotic therapies |
| EP2027153B1 (en) | 2006-05-25 | 2014-04-30 | Bayer Intellectual Property GmbH | Dimeric molecular complexes |
| US20070274985A1 (en) | 2006-05-26 | 2007-11-29 | Stefan Dubel | Antibody |
| EP2418223A3 (en) | 2006-06-12 | 2013-01-16 | Emergent Product Development Seattle, LLC | Single-chain multivalent binding proteins with effector function |
| WO2008022349A2 (en) | 2006-08-18 | 2008-02-21 | Armagen Technologies, Inc. | Agents for blood-brain barrier delivery |
| KR101428116B1 (ko) | 2006-08-21 | 2014-08-07 | 제넨테크, 인크. | 아자-벤조푸라닐 화합물 및 사용 방법 |
| US10118970B2 (en) | 2006-08-30 | 2018-11-06 | Genentech, Inc. | Multispecific antibodies |
| US8877780B2 (en) | 2006-08-30 | 2014-11-04 | Celgene Corporation | 5-substituted isoindoline compounds |
| EP2083868A2 (en) | 2006-10-04 | 2009-08-05 | Københavns Universitet | Generation of a cancer-specific immune response toward muc1 and cancer specific muc1 antibodies |
| FR2906808B1 (fr) | 2006-10-10 | 2012-10-05 | Univ Nantes | Utilisation d'anticorps monoclonaux specifiques de la forme o-acetylee du ganglioside gd2 dans le traitement de certains cancers |
| US20080254512A1 (en) | 2006-11-02 | 2008-10-16 | Capon Daniel J | Hybrid immunoglobulins with moving parts |
| MX2009005144A (es) | 2006-11-22 | 2009-05-27 | Incyte Corp | Imidazotriazinas e imidazopirimidinas como inhibidores de cinasa. |
| CA2669579A1 (en) | 2006-11-23 | 2008-05-29 | Novartis Ag | 5-sulfanylmethyl-pyrazolo [1,5-a] pyrimidin-7-ol derivatives as cxcr2 antagonists |
| MX2009005363A (es) | 2006-11-23 | 2009-06-05 | Novartis Ag | Pirimidinas y su uso como antagonistas del receptor cxcr2. |
| BRPI0718947A2 (pt) | 2006-11-23 | 2013-12-17 | Novartis Ag | Derivados de 5-sulfanilmetil-[1,2,4] triazol [1,5-a] pirimidin-7-ol como antagonistas de cxcr2 |
| WO2008101234A2 (en) | 2007-02-16 | 2008-08-21 | Sloan-Kettering Institute For Cancer Research | Anti ganglioside gd3 antibodies and uses thereof |
| WO2008103645A2 (en) | 2007-02-19 | 2008-08-28 | Wisconsin Alumni Research Foundation | Prostate cancer and melanoma antigens |
| US20100158927A1 (en) | 2007-03-29 | 2010-06-24 | Technion Research & Development Foundation Ltd. | Antibodies, methods and kits for diagnosing and treating melanoma |
| ES2667863T3 (es) | 2007-03-29 | 2018-05-14 | Genmab A/S | Anticuerpos biespecíficos y métodos de producción de los mismos |
| WO2008127735A1 (en) | 2007-04-13 | 2008-10-23 | Stemline Therapeutics, Inc. | Il3ralpha antibody conjugates and uses thereof |
| CA2682605A1 (en) | 2007-04-18 | 2008-10-30 | Zymogenetics, Inc. | Single chain fc, methods of making and methods of treatment |
| US9244059B2 (en) | 2007-04-30 | 2016-01-26 | Immutep Parc Club Orsay | Cytotoxic anti-LAG-3 monoclonal antibody and its use in the treatment or prevention of organ transplant rejection and autoimmune disease |
| CL2008001234A1 (es) | 2007-04-30 | 2008-09-22 | Genentech Inc | Compuestos derivados de heterociclos nitrogenados, inhibidores de las proteinas de apoptosis; y uso en el tratamiento del cancer. |
| EP1987839A1 (en) | 2007-04-30 | 2008-11-05 | I.N.S.E.R.M. Institut National de la Sante et de la Recherche Medicale | Cytotoxic anti-LAG-3 monoclonal antibody and its use in the treatment or prevention of organ transplant rejection and autoimmune disease |
| EP2160401B1 (en) | 2007-05-11 | 2014-09-24 | Altor BioScience Corporation | Fusion molecules and il-15 variants |
| JP2010190572A (ja) | 2007-06-01 | 2010-09-02 | Sapporo Medical Univ | IL13Ra2に対する抗体およびこれを含む診断・治療薬 |
| EP2535354B1 (en) | 2007-06-18 | 2017-01-11 | Merck Sharp & Dohme B.V. | Antibodies to human programmed death receptor pd-1 |
| AU2008282863A1 (en) | 2007-07-31 | 2009-02-05 | Merck Sharp & Dohme Corp. | IGF-1R specific antibodies useful in the detection and diagnosis of cellular proliferative disorders |
| CN101952312A (zh) | 2007-07-31 | 2011-01-19 | 米迪缪尼有限公司 | 多特异性表位结合蛋白及其应用 |
| ES2628395T3 (es) | 2007-08-15 | 2017-08-02 | Bayer Pharma Aktiengesellschaft | Anticuerpo regulado por proteasa |
| CA2699202C (en) | 2007-09-12 | 2016-09-27 | F. Hoffmann-La Roche Ag | Combinations of phosphoinositide 3-kinase inhibitor compounds and chemotherapeutic agents, and methods of use |
| AU2008308956B2 (en) | 2007-10-01 | 2013-03-14 | Bristol-Myers Squibb Company | Human antibodies that bind mesothelin, and uses thereof |
| EP2044949A1 (en) | 2007-10-05 | 2009-04-08 | Immutep | Use of recombinant lag-3 or the derivatives thereof for eliciting monocyte immune response |
| US8354528B2 (en) | 2007-10-25 | 2013-01-15 | Genentech, Inc. | Process for making thienopyrimidine compounds |
| JP5608091B2 (ja) | 2007-11-26 | 2014-10-15 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 抗メソセリン抗体およびその使用 |
| AU2008328779B2 (en) | 2007-11-27 | 2014-06-05 | Ablynx N.V. | Amino acid sequences directed against HER2 and polypeptides comprising the same for the treatment of cancers and/or tumors |
| UY31504A1 (es) | 2007-11-30 | 2009-07-17 | Construcciones de union de antigenos | |
| EP2690101B1 (en) | 2007-12-19 | 2015-06-24 | Genentech, Inc. | 5-Anilinoimidazopyridines and Methods of Use |
| US8227577B2 (en) | 2007-12-21 | 2012-07-24 | Hoffman-La Roche Inc. | Bivalent, bispecific antibodies |
| US20090162359A1 (en) | 2007-12-21 | 2009-06-25 | Christian Klein | Bivalent, bispecific antibodies |
| US9266967B2 (en) | 2007-12-21 | 2016-02-23 | Hoffmann-La Roche, Inc. | Bivalent, bispecific antibodies |
| US8242247B2 (en) | 2007-12-21 | 2012-08-14 | Hoffmann-La Roche Inc. | Bivalent, bispecific antibodies |
| ES2563027T3 (es) | 2008-01-07 | 2016-03-10 | Amgen Inc. | Método para fabricación de moléculas heterodímeras Fc de anticuerpos utilizando efectos de conducción electrostática |
| CN104548091A (zh) | 2008-02-11 | 2015-04-29 | 治疗科技公司 | 用于肿瘤治疗的单克隆抗体 |
| BRPI0908529A2 (pt) | 2008-02-26 | 2015-09-29 | Novartis Ag | composto orgânicos |
| US8168757B2 (en) | 2008-03-12 | 2012-05-01 | Merck Sharp & Dohme Corp. | PD-1 binding proteins |
| AR071891A1 (es) | 2008-05-30 | 2010-07-21 | Imclone Llc | Anticuerpos humanos anti-flt3 (receptor tirosina cinasa 3 tipo fms humano) |
| US8168784B2 (en) | 2008-06-20 | 2012-05-01 | Abbott Laboratories | Processes to make apoptosis promoters |
| GB0906579D0 (en) | 2009-04-16 | 2009-05-20 | Vernalis R&D Ltd | Pharmaceuticals, compositions and methods of making and using the same |
| UA103198C2 (en) | 2008-08-04 | 2013-09-25 | Новартис Аг | Squaramide derivatives as cxcr2 antagonists |
| AR072999A1 (es) | 2008-08-11 | 2010-10-06 | Medarex Inc | Anticuerpos humanos que se unen al gen 3 de activacion linfocitaria (lag-3) y los usos de estos |
| CN102186856B (zh) | 2008-08-22 | 2014-09-24 | 诺华股份有限公司 | 作为cdk抑制剂的吡咯并嘧啶化合物 |
| EA023148B1 (ru) | 2008-08-25 | 2016-04-29 | Эмплиммьюн, Инк. | Композиции на основе антагонистов pd-1 и их применение |
| US20110159023A1 (en) | 2008-08-25 | 2011-06-30 | Solomon Langermann | Pd-1 antagonists and methods for treating infectious disease |
| WO2010029435A1 (en) | 2008-09-12 | 2010-03-18 | Isis Innovation Limited | Pd-1 specific antibodies and uses thereof |
| US8486393B2 (en) | 2008-09-19 | 2013-07-16 | University of Pittsburgh—of the Commonwealth System of Higher Education | Monoclonal antibodies for CSPG4 for the diagnosis and treatment of basal breast carcinoma |
| HUE030807T2 (en) | 2008-09-26 | 2017-05-29 | Dana Farber Cancer Inst Inc | Human anti-PD-1, anti-PD-L1 and anti-PD-L2 antibodies and their applications |
| WO2010063802A1 (en) | 2008-12-05 | 2010-06-10 | Novartis Ag | 3, 4-di-substituted cyclobutene- 1, 2 -diones as cxcr2 receptor antagonists |
| TWI729512B (zh) | 2008-12-09 | 2021-06-01 | 美商建南德克公司 | 抗pd-l1抗體及其於增進t細胞功能之用途 |
| EP2210891A1 (en) | 2009-01-26 | 2010-07-28 | Domain Therapeutics | New adenosine receptor ligands and uses thereof |
| EP3192811A1 (en) | 2009-02-09 | 2017-07-19 | Université d'Aix-Marseille | Pd-1 antibodies and pd-l1 antibodies and uses thereof |
| PL2408775T3 (pl) | 2009-03-20 | 2015-10-30 | Alfasigma Spa | Utlenione pochodne triazolilopurynowe użyteczne jako ligandy receptora adenozynowego a2a i ich zastosowanie jako leków |
| CA2756988A1 (en) | 2009-04-01 | 2010-10-07 | Genentech, Inc. | Anti-fcrh5 antibodies and immunoconjugates |
| EP2414399A1 (en) | 2009-04-01 | 2012-02-08 | F. Hoffmann-La Roche AG | Anti-fcrh5 antibodies and immunoconjugates and methods of use |
| EP2424567B1 (en) | 2009-04-27 | 2018-11-21 | OncoMed Pharmaceuticals, Inc. | Method for making heteromultimeric molecules |
| PL2426148T3 (pl) | 2009-04-27 | 2016-01-29 | Kyowa Hakko Kirin Co Ltd | Przeciwciało anty-IL-3RA do stosowania w leczeniu nowotworu krwi |
| TWI445708B (zh) | 2009-09-02 | 2014-07-21 | Irm Llc | 作為tlr活性調節劑之化合物及組合物 |
| CN102574924A (zh) | 2009-09-03 | 2012-07-11 | 先灵公司 | 抗-gitr抗体 |
| EP2504028A4 (en) | 2009-11-24 | 2014-04-09 | Amplimmune Inc | SIMULTANEOUS INHIBITION OF PD-L1 / PD-L2 |
| CN104961829B (zh) | 2009-11-24 | 2018-08-21 | 米迪缪尼有限公司 | 针对b7-h1的靶向结合剂 |
| WO2011069019A2 (en) | 2009-12-02 | 2011-06-09 | David Ho | J591 minibodies and cys-diabodies for targeting human prostate specific membrane antigen (psma) and methods for their use |
| US8440693B2 (en) | 2009-12-22 | 2013-05-14 | Novartis Ag | Substituted isoquinolinones and quinazolinones |
| HRP20160422T1 (hr) | 2009-12-23 | 2016-05-20 | Synimmune Gmbh | Protutijela protiv flt3 postupci njihove upotrebe |
| HUE028640T2 (en) | 2010-02-05 | 2016-12-28 | Heptares Therapeutics Ltd | 1,2,4-triazin-4-amine derivative |
| KR20230044026A (ko) | 2010-02-24 | 2023-03-31 | 이뮤노젠 아이엔씨 | 엽산염 수용체 1 항체와 면역접합체 및 이들의 용도 |
| CN102892786B (zh) | 2010-03-11 | 2016-03-16 | Ucb医药有限公司 | Pd-1抗体 |
| ES2365960B1 (es) | 2010-03-31 | 2012-06-04 | Palobiofarma, S.L | Nuevos antagonistas de los receptores de adenosina. |
| US9150663B2 (en) | 2010-04-20 | 2015-10-06 | Genmab A/S | Heterodimeric antibody Fc-containing proteins and methods for production thereof |
| ES2627692T3 (es) | 2010-06-10 | 2017-07-31 | Aragon Pharmaceuticals, Inc. | Moduladores de receptores de estrógenos y usos de los mismos |
| CN103079644B (zh) | 2010-06-11 | 2017-02-15 | 协和发酵麒麟株式会社 | 抗tim‑3抗体 |
| WO2011159847A2 (en) | 2010-06-15 | 2011-12-22 | The Regents Of The University Of California | Receptor tyrosine kinase-like orphan receptor 1 (ror1) single chain fv antibody fragment conjugates and methods of use thereof |
| US8853423B2 (en) | 2010-06-17 | 2014-10-07 | Seragon Pharmaceuticals, Inc. | Indane estrogen receptor modulators and uses thereof |
| JP2013532153A (ja) | 2010-06-18 | 2013-08-15 | ザ ブリガム アンド ウィメンズ ホスピタル インコーポレイテッド | 慢性免疫病に対する免疫治療のためのtim−3およびpd−1に対する二重特異性抗体 |
| US9315585B2 (en) | 2010-06-19 | 2016-04-19 | Memorial Sloan Kettering Cancer Center | Anti-GD2 antibodies |
| US8907053B2 (en) | 2010-06-25 | 2014-12-09 | Aurigene Discovery Technologies Limited | Immunosuppression modulating compounds |
| EP3467101A3 (en) | 2010-09-08 | 2019-06-19 | Baylor College of Medicine | Immunotherapy of brain tumor using geneticially engineered gd2-specific t cells |
| GB2483736B (en) | 2010-09-16 | 2012-08-29 | Aragon Pharmaceuticals Inc | Estrogen receptor modulators and uses thereof |
| WO2012062713A1 (en) | 2010-11-08 | 2012-05-18 | Novartis Ag | Cxcr2 binding polypeptides |
| PH12013501201A1 (en) | 2010-12-09 | 2013-07-29 | Univ Pennsylvania | Use of chimeric antigen receptor-modified t cells to treat cancer |
| JOP20210044A1 (ar) | 2010-12-30 | 2017-06-16 | Takeda Pharmaceuticals Co | الأجسام المضادة لـ cd38 |
| EA201391449A1 (ru) | 2011-04-01 | 2014-03-31 | Мемориал Слоан-Кеттеринг Кэнсер Сентер | Антитела против пептидов цитозоля |
| DK2699264T3 (en) | 2011-04-20 | 2018-06-25 | Medimmune Llc | ANTIBODIES AND OTHER MOLECULES BINDING B7-H1 AND PD-1 |
| AR086044A1 (es) | 2011-05-12 | 2013-11-13 | Imclone Llc | Anticuerpos que se unen especificamente a un dominio extracelular de c-kit y usos de los mismos |
| US20140105915A1 (en) | 2011-05-27 | 2014-04-17 | Glaxo Group Limited | Bcma (cd269/tnfrsf17) - binding proteins |
| MY171135A (en) | 2011-06-03 | 2019-09-27 | Xoma Technology Ltd | Antibodies specific for tgf-beta |
| EP2537933A1 (en) | 2011-06-24 | 2012-12-26 | Institut National de la Santé et de la Recherche Médicale (INSERM) | An IL-15 and IL-15Ralpha sushi domain based immunocytokines |
| WO2013006490A2 (en) | 2011-07-01 | 2013-01-10 | Cellerant Therapeutics, Inc. | Antibodies that specifically bind to tim3 |
| BR122022000334B1 (pt) | 2011-08-01 | 2023-03-21 | Genentech, Inc | Composição farmacêutica compreendendo um antagonista de ligação ao eixo pd-1 e um inibidor de mek |
| EP2760821B1 (en) | 2011-09-02 | 2017-10-11 | Novartis AG | Choline salt of an anti-inflammatory substituted cyclobutenedione compound |
| US20140255363A1 (en) | 2011-09-16 | 2014-09-11 | Baylor College Of Medicine | Targeting the tumor microenvironment using manipulated nkt cells |
| SG11201400527XA (en) | 2011-09-16 | 2014-04-28 | Univ Pennsylvania | Rna engineered t cells for the treatment of cancer |
| ITMO20110270A1 (it) | 2011-10-25 | 2013-04-26 | Sara Caldrer | Una cellula effettrice modificata per il trattamento di neoplasie esprimenti il disialonganglioside gd2 |
| SI2771364T1 (sl) | 2011-10-27 | 2019-10-30 | Genmab As | Produkcija heterodimernih proteinov |
| WO2013063419A2 (en) | 2011-10-28 | 2013-05-02 | The Trustees Of The University Of Pennsylvania | A fully human, anti-mesothelin specific chimeric immune receptor for redirected mesothelin-expressing cell targeting |
| US10391126B2 (en) | 2011-11-18 | 2019-08-27 | Board Of Regents, The University Of Texas System | CAR+ T cells genetically modified to eliminate expression of T-cell receptor and/or HLA |
| KR101981873B1 (ko) | 2011-11-28 | 2019-05-23 | 메르크 파텐트 게엠베하 | 항-pd-l1 항체 및 그의 용도 |
| US9439768B2 (en) | 2011-12-08 | 2016-09-13 | Imds Llc | Glenoid vault fixation |
| JO3357B1 (ar) | 2012-01-26 | 2019-03-13 | Novartis Ag | مركبات إيميدازوبيروليدينون |
| EP3594245A1 (en) | 2012-02-13 | 2020-01-15 | Seattle Children's Hospital d/b/a Seattle Children's Research Institute | Bispecific chimeric antigen receptors and therapeutic uses thereof |
| KR20140127816A (ko) | 2012-02-22 | 2014-11-04 | 더 트러스티스 오브 더 유니버시티 오브 펜실바니아 | 암의 치료에 유용한 t 세포의 지속성 집단을 생성시키기 위한 조성물 및 방법 |
| CA3116051C (en) | 2012-03-23 | 2023-09-26 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Anti-mesothelin chimeric antigen receptors |
| US9056910B2 (en) | 2012-05-01 | 2015-06-16 | Genentech, Inc. | Anti-PMEL17 antibodies and immunoconjugates |
| US9328174B2 (en) | 2012-05-09 | 2016-05-03 | Novartis Ag | Chemokine receptor binding polypeptides |
| EP4053162A1 (en) | 2012-05-18 | 2022-09-07 | Aptevo Research and Development LLC | Bispecific scfv immunofusion (bif) binding to cd123 and cd3 |
| WO2013179174A1 (en) | 2012-05-29 | 2013-12-05 | Koninklijke Philips N.V. | Lighting arrangement |
| KR102410078B1 (ko) | 2012-05-31 | 2022-06-22 | 소렌토 쎄라퓨틱스, 인코포레이티드 | Pd-l1에 결합하는 항원 결합 단백질 |
| WO2013192294A1 (en) | 2012-06-20 | 2013-12-27 | Boston 3T Biotechnologies, Inc. | Cellular therapies for treating and preventing cancers and other immune system disorders |
| UY34887A (es) | 2012-07-02 | 2013-12-31 | Bristol Myers Squibb Company Una Corporacion Del Estado De Delaware | Optimización de anticuerpos que se fijan al gen de activación de linfocitos 3 (lag-3) y sus usos |
| EP2890715B1 (en) | 2012-08-03 | 2020-12-16 | Dana-Farber Cancer Institute, Inc. | Single agent anti-pd-l1 and pd-l2 dual binding antibodies and methods of use |
| IL293944A (en) | 2012-08-20 | 2022-08-01 | Hutchinson Fred Cancer Res | Method and preparations for cellular immunotherapy |
| WO2014043708A1 (en) | 2012-09-17 | 2014-03-20 | Traber Peter G | Method for enhancing specific immunotherapies in cancer treatment |
| WO2014055897A2 (en) | 2012-10-04 | 2014-04-10 | Dana-Farber Cancer Institute, Inc. | Human monoclonal anti-pd-l1 antibodies and methods of use |
| NZ630790A (en) | 2012-10-24 | 2016-11-25 | Admune Therapeutics Llc | Il-15r alpha forms, cells expressing il-15r alpha forms, and therapeutic uses of il-15r alpha and il-15/il-15r alpha complexes |
| TW201425336A (zh) | 2012-12-07 | 2014-07-01 | Amgen Inc | Bcma抗原結合蛋白質 |
| AR093984A1 (es) | 2012-12-21 | 2015-07-01 | Merck Sharp & Dohme | Anticuerpos que se unen a ligando 1 de muerte programada (pd-l1) humano |
| JP2016507523A (ja) | 2013-02-05 | 2016-03-10 | エンクマフ アーゲー | CD3εおよびBCMAに対する二重特異的抗体 |
| SI2958907T1 (en) | 2013-02-19 | 2018-05-31 | Novartis Ag | Benzothiophene derivatives and their compositions as selective estrogen receptor antagonists |
| US9573988B2 (en) | 2013-02-20 | 2017-02-21 | Novartis Ag | Effective targeting of primary human leukemia using anti-CD123 chimeric antigen receptor engineered T cells |
| CN111139256A (zh) | 2013-02-20 | 2020-05-12 | 诺华股份有限公司 | 使用人源化抗EGFRvIII嵌合抗原受体治疗癌症 |
| US20160031996A1 (en) | 2013-03-14 | 2016-02-04 | Csl Limited | Anti il-3r alpha agents and uses thereof |
| WO2014138819A1 (en) | 2013-03-14 | 2014-09-18 | Csl Limited | Agents that neutralize il-3 signaling and uses thereof |
| US9657105B2 (en) | 2013-03-15 | 2017-05-23 | City Of Hope | CD123-specific chimeric antigen receptor redirected T cells and methods of their use |
| AR095374A1 (es) | 2013-03-15 | 2015-10-14 | Amgen Res Munich Gmbh | Moléculas de unión para bcma y cd3 |
| MY210104A (en) | 2013-03-15 | 2025-08-27 | Glaxosmithkline Ip Dev Ltd | Anti-lag-3 binding proteins |
| UY35468A (es) | 2013-03-16 | 2014-10-31 | Novartis Ag | Tratamiento de cáncer utilizando un receptor quimérico de antígeno anti-cd19 |
| WO2014165707A2 (en) | 2013-04-03 | 2014-10-09 | Memorial Sloan-Kettering Cancer Center | Effective generation of tumor-targeted t-cells derived from pluripotent stem cells |
| PT2992017T (pt) | 2013-05-02 | 2021-01-29 | Anaptysbio Inc | Anticorpos dirigidos contra a morte programada 1 (pd-1) |
| HK1221964A1 (zh) | 2013-05-31 | 2017-06-16 | Sorrento Therapeutics, Inc. | 与pd-1结合的抗原结合蛋白 |
| AR096687A1 (es) | 2013-06-24 | 2016-01-27 | Genentech Inc | Anticuerpos anti-fcrh5 |
| US20160145355A1 (en) | 2013-06-24 | 2016-05-26 | Biomed Valley Discoveries, Inc. | Bispecific antibodies |
| AR097306A1 (es) | 2013-08-20 | 2016-03-02 | Merck Sharp & Dohme | Modulación de la inmunidad tumoral |
| TW201605896A (zh) | 2013-08-30 | 2016-02-16 | 安美基股份有限公司 | Gitr抗原結合蛋白 |
| RS63571B9 (sr) | 2013-09-13 | 2023-02-28 | Beigene Switzerland Gmbh | Anti-pd1 antitela i njihova primena kao terapeutska i dijagnostička sredstva |
| AU2014339900B2 (en) | 2013-10-25 | 2019-10-24 | Dana-Farber Cancer Institute, Inc. | Anti-PD-L1 monoclonal antibodies and fragments thereof |
| WO2015081158A1 (en) | 2013-11-26 | 2015-06-04 | Bristol-Myers Squibb Company | Method of treating hiv by disrupting pd-1/pd-l1 signaling |
| PL3081576T3 (pl) | 2013-12-12 | 2020-03-31 | Shanghai Hengrui Pharmaceutical Co., Ltd. | Przeciwciało anty pd-1, jego fragment wiążący antygen i ich zastosowanie medyczne |
| US10640569B2 (en) | 2013-12-19 | 2020-05-05 | Novartis Ag | Human mesothelin chimeric antigen receptors and uses thereof |
| HUE057917T2 (hu) | 2014-01-15 | 2022-06-28 | Kadmon Corp Llc | Immunmodulátor szerek |
| WO2015112534A2 (en) | 2014-01-21 | 2015-07-30 | Medimmune, Llc | Compositions and methods for modulating and redirecting immune responses |
| TWI681969B (zh) | 2014-01-23 | 2020-01-11 | 美商再生元醫藥公司 | 針對pd-1的人類抗體 |
| TWI680138B (zh) | 2014-01-23 | 2019-12-21 | 美商再生元醫藥公司 | 抗pd-l1之人類抗體 |
| JOP20200094A1 (ar) | 2014-01-24 | 2017-06-16 | Dana Farber Cancer Inst Inc | جزيئات جسم مضاد لـ pd-1 واستخداماتها |
| PT3556775T (pt) | 2014-01-28 | 2021-12-31 | Bristol Myers Squibb Co | Anticorpos anti-lag-3 para tratar neoplasias malignas hematológicas |
| JOP20200096A1 (ar) | 2014-01-31 | 2017-06-16 | Children’S Medical Center Corp | جزيئات جسم مضاد لـ tim-3 واستخداماتها |
| BR112016020953A2 (pt) | 2014-03-13 | 2018-01-23 | Hoffmann La Roche | composto, kit, composição farmacêutica, uso de composto, método de tratamento e invenção |
| EP3660050A1 (en) | 2014-03-14 | 2020-06-03 | Novartis AG | Antibody molecules to lag-3 and uses thereof |
| WO2015142675A2 (en) | 2014-03-15 | 2015-09-24 | Novartis Ag | Treatment of cancer using chimeric antigen receptor |
| TW202132337A (zh) | 2014-05-28 | 2021-09-01 | 美商艾吉納斯公司 | 抗糖皮質素誘導性tnfr家族相關性受體(gitr)抗體類及使用彼等之方法 |
| EP3149042B1 (en) | 2014-05-29 | 2019-08-28 | Spring Bioscience Corporation | Pd-l1 antibodies and uses thereof |
| AU2015271709B2 (en) | 2014-06-06 | 2020-11-26 | Bristol-Myers Squibb Company | Antibodies against glucocorticoid-induced tumor necrosis factor receptor (GITR) and uses thereof |
| WO2015195163A1 (en) | 2014-06-20 | 2015-12-23 | R-Pharm Overseas, Inc. | Pd-l1 antagonist fully human antibody |
| TWI693232B (zh) | 2014-06-26 | 2020-05-11 | 美商宏觀基因股份有限公司 | 與pd-1和lag-3具有免疫反應性的共價結合的雙抗體和其使用方法 |
| US10544225B2 (en) | 2014-07-03 | 2020-01-28 | Beigene, Ltd. | Anti-PD-L1 antibodies and their use as therapeutics and diagnostics |
| CN107109420A (zh) | 2014-07-21 | 2017-08-29 | 诺华股份有限公司 | 使用cll-1嵌合抗原受体的癌症治疗 |
| SG10201913765YA (en) | 2014-07-21 | 2020-03-30 | Novartis Ag | Treatment of cancer using a cd33 chimeric antigen receptor |
| JP7054622B2 (ja) | 2014-07-21 | 2022-04-14 | ノバルティス アーゲー | ヒト化抗bcmaキメラ抗原受容体を使用した癌の処置 |
| KR102523934B1 (ko) | 2014-07-24 | 2023-04-20 | 2세븐티 바이오, 인코포레이티드 | Bcma 키메릭 항원 수용체 |
| JO3663B1 (ar) | 2014-08-19 | 2020-08-27 | Merck Sharp & Dohme | الأجسام المضادة لمضاد lag3 وأجزاء ربط الأنتيجين |
| AU2015305531B2 (en) | 2014-08-19 | 2021-05-20 | Novartis Ag | Anti-CD123 chimeric antigen receptor (CAR) for use in cancer treatment |
| CA2962976A1 (en) | 2014-10-03 | 2016-04-07 | Dana-Farber Cancer Institute, Inc. | Glucocorticoid-induced tumor necrosis factor receptor (gitr) antibodies and methods of use thereof |
| MA41044A (fr) | 2014-10-08 | 2017-08-15 | Novartis Ag | Compositions et procédés d'utilisation pour une réponse immunitaire accrue et traitement contre le cancer |
| CN114920840A (zh) | 2014-10-14 | 2022-08-19 | 诺华股份有限公司 | 针对pd-l1的抗体分子及其用途 |
| EP3215532B1 (en) | 2014-11-06 | 2019-10-23 | F.Hoffmann-La Roche Ag | Anti-tim3 antibodies and methods of use |
| HK1246304A1 (zh) | 2014-11-11 | 2018-09-07 | Medimmune Limited | 包含抗cd73抗体和a2a受体抑制剂的治疗组合及其用途 |
| TWI595006B (zh) | 2014-12-09 | 2017-08-11 | 禮納特神經系統科學公司 | 抗pd-1抗體類和使用彼等之方法 |
| US20160200815A1 (en) | 2015-01-05 | 2016-07-14 | Jounce Therapeutics, Inc. | Antibodies that inhibit tim-3:lilrb2 interactions and uses thereof |
| JP2018510151A (ja) | 2015-03-06 | 2018-04-12 | ソレント・セラピューティクス・インコーポレイテッド | Tim3に結合する抗体医薬 |
| IL283006B2 (en) | 2015-04-01 | 2023-10-01 | Anaptysbio Inc | Antibodies directed against t cell immunoglobulin and mucin protein 3 (tim-3) |
| CA2988115A1 (en) | 2015-06-03 | 2016-12-08 | Bristol-Myers Squibb Company | Anti-gitr antibodies for cancer diagnostics |
| RU2753439C2 (ru) | 2015-07-23 | 2021-08-16 | Инхибркс, Инк. | Поливалетные и полиспецифичные gitr-связывающие слитые белки |
| SI3334431T1 (sl) | 2015-08-11 | 2020-01-31 | Novartis Ag | 5-bromo-2,6-di-(1h-pirazol-l-il)pyrimidin-4-amin za uporabo v zdravljenju raka |
| KR20180033588A (ko) | 2015-08-12 | 2018-04-03 | 메디뮨 리미티드 | Gitrl 융합 단백질 및 그의 용도 |
| CA2995365C (en) | 2015-08-13 | 2021-10-12 | Merck Sharp & Dohme Corp. | Cyclic di-nucleotide compounds as sting agonists |
| CA3038979A1 (en) * | 2016-10-11 | 2018-04-19 | Arvinas, Inc. | Compounds and methods for the targeted degradation of androgen receptor |
| RS64976B1 (sr) * | 2016-12-01 | 2024-01-31 | Arvinas Operations Inc | Derivati tetrahidronaftalena i tetrahidroizohinolina kao degradatori estrogenih receptora |
| CN117551089A (zh) * | 2017-01-26 | 2024-02-13 | 阿尔维纳斯运营股份有限公司 | 雌激素受体蛋白水解调节剂及相关使用方法 |
| TWI793151B (zh) * | 2017-08-23 | 2023-02-21 | 瑞士商諾華公司 | 3-(1-氧異吲哚啉-2-基)之氫吡啶-2,6-二酮衍生物及其用途 |
| CA3079407A1 (en) * | 2017-10-18 | 2019-04-25 | Novartis Ag | Compositions and methods for selective protein degradation |
| AR116109A1 (es) * | 2018-07-10 | 2021-03-31 | Novartis Ag | Derivados de 3-(5-amino-1-oxoisoindolin-2-il)piperidina-2,6-diona y usos de los mismos |
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| MX2021009763A (es) | 2021-09-08 |
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