EA029046B1 - Пирролобензодиазепины и промежуточные соединения для их получения, способы их синтеза - Google Patents
Пирролобензодиазепины и промежуточные соединения для их получения, способы их синтеза Download PDFInfo
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- EA029046B1 EA029046B1 EA201490550A EA201490550A EA029046B1 EA 029046 B1 EA029046 B1 EA 029046B1 EA 201490550 A EA201490550 A EA 201490550A EA 201490550 A EA201490550 A EA 201490550A EA 029046 B1 EA029046 B1 EA 029046B1
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- Eurasian Patent Office
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- 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
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- 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
- C07D401/12—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 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
- C07D409/02—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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen 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
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161547207P | 2011-10-14 | 2011-10-14 | |
| PCT/EP2012/070232 WO2013053872A1 (en) | 2011-10-14 | 2012-10-12 | Synthesis method and intermediates useful in the preparation of pyrrolobenzodiazepines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201490550A1 EA201490550A1 (ru) | 2014-09-30 |
| EA029046B1 true EA029046B1 (ru) | 2018-02-28 |
Family
ID=47019019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201490550A EA029046B1 (ru) | 2011-10-14 | 2012-10-12 | Пирролобензодиазепины и промежуточные соединения для их получения, способы их синтеза |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9102704B2 (cg-RX-API-DMAC10.html) |
| EP (1) | EP2751076B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JP6166728B2 (cg-RX-API-DMAC10.html) |
| CN (1) | CN104011018B (cg-RX-API-DMAC10.html) |
| AU (1) | AU2012322933B2 (cg-RX-API-DMAC10.html) |
| BR (1) | BR112014009070B1 (cg-RX-API-DMAC10.html) |
| CA (1) | CA2850096C (cg-RX-API-DMAC10.html) |
| EA (1) | EA029046B1 (cg-RX-API-DMAC10.html) |
| WO (1) | WO2013053872A1 (cg-RX-API-DMAC10.html) |
Families Citing this family (98)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0819095D0 (en) | 2008-10-17 | 2008-11-26 | Spirogen Ltd | Pyrrolobenzodiazepines |
| MX368648B (es) | 2010-04-15 | 2019-10-09 | Seattle Genetics Inc | Pirrolobenzodiazepinas usadas para tratar enfermedades proliferativas. |
| CN103068405A (zh) | 2010-04-15 | 2013-04-24 | 西雅图基因公司 | 靶向吡咯并苯并二氮杂卓结合物 |
| US9399641B2 (en) | 2011-09-20 | 2016-07-26 | Medimmune Limited | Pyrrolobenzodiazepines as unsymmetrical dimeric PBD compounds for inclusion in targeted conjugates |
| CA2850264C (en) | 2011-10-14 | 2019-11-05 | Medimmune Limited | Pyrrolobenzodiazepines |
| CA2850373C (en) | 2011-10-14 | 2019-07-16 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines and targeted conjugates |
| AU2012322934B2 (en) | 2011-10-14 | 2016-09-08 | Medimmune Limited | Pyrrolobenzodiazepines |
| CA2850375C (en) | 2011-10-14 | 2019-07-02 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines and targeted conjugates |
| EP2906297B1 (en) | 2012-10-12 | 2017-12-06 | ADC Therapeutics SA | Pyrrolobenzodiazepine-antibody conjugates |
| BR112015008238A2 (pt) | 2012-10-12 | 2017-11-28 | Adc Therapeutics Sarl | conjugados de pirrolbenzodiazepina-anticorpo anti-cd22 |
| PT2906253T (pt) | 2012-10-12 | 2018-11-05 | Medimmune Ltd | Conjugados de anticorpo anti-psma de pirrolobenzodiazepina |
| PT2906248T (pt) | 2012-10-12 | 2019-03-04 | Medimmune Ltd | Pirrolobenzodiazepinas e conjugados das mesmas |
| KR101995620B1 (ko) | 2012-10-12 | 2019-07-03 | 에이디씨 테라퓨틱스 에스에이 | 피롤로벤조디아제핀-항체 컨주게이트 |
| EP2906249B1 (en) | 2012-10-12 | 2018-06-27 | MedImmune Limited | Synthesis and intermediates of pyrrolobenzodiazepine derivatives for conjugation |
| DK2839860T3 (da) | 2012-10-12 | 2019-06-17 | Medimmune Ltd | Pyrrolobenzodiazepiner og konjugater deraf |
| WO2014057114A1 (en) | 2012-10-12 | 2014-04-17 | Adc Therapeutics Sàrl | Pyrrolobenzodiazepine-anti-psma antibody conjugates |
| DK2906298T3 (en) | 2012-10-12 | 2018-12-17 | Adc Therapeutics Sa | Pyrrolobenzodiazepine-antibody conjugates |
| US9567340B2 (en) | 2012-12-21 | 2017-02-14 | Medimmune Limited | Unsymmetrical pyrrolobenzodiazepines-dimers for use in the treatment of proliferative and autoimmune diseases |
| AU2013366493B2 (en) | 2012-12-21 | 2017-08-24 | Medimmune Limited | Pyrrolobenzodiazepines and conjugates thereof |
| MX363787B (es) | 2013-03-13 | 2019-04-03 | Medimmune Ltd | Pirrolobenzodiazepinas y conjugados de los mismos. |
| KR102066318B1 (ko) | 2013-03-13 | 2020-01-14 | 메디뮨 리미티드 | 피롤로벤조디아제핀 및 그의 컨쥬게이트 |
| EP3964237B1 (en) | 2013-03-15 | 2026-02-18 | Regeneron Pharmaceuticals, Inc. | Biologically active molecules, conjugates thereof, and therapeutic uses |
| AU2014311361B2 (en) | 2013-08-26 | 2018-11-29 | Regeneron Pharmaceuticals, Inc. | Pharmaceutical compositions comprising macrolide diastereomers, methods of their synthesis and therapeutic uses |
| WO2015052534A1 (en) | 2013-10-11 | 2015-04-16 | Spirogen Sàrl | Pyrrolobenzodiazepine-antibody conjugates |
| WO2015052535A1 (en) | 2013-10-11 | 2015-04-16 | Spirogen Sàrl | Pyrrolobenzodiazepine-antibody conjugates |
| US10010624B2 (en) | 2013-10-11 | 2018-07-03 | Medimmune Limited | Pyrrolobenzodiazepine-antibody conjugates |
| GB201317981D0 (en) | 2013-10-11 | 2013-11-27 | Spirogen Sarl | Pyrrolobenzodiazepines and conjugates thereof |
| GB201317982D0 (en) * | 2013-10-11 | 2013-11-27 | Spirogen Sarl | Pyrrolobenzodiazepines and conjugates thereof |
| AU2015229591B2 (en) | 2014-03-11 | 2020-10-22 | Regeneron Pharmaceuticals, Inc. | Anti-EGFRvlll antibodies and uses thereof |
| EP3193940A1 (en) | 2014-09-10 | 2017-07-26 | Medimmune Limited | Pyrrolobenzodiazepines and conjugates thereof |
| GB201416112D0 (en) | 2014-09-12 | 2014-10-29 | Medimmune Ltd | Pyrrolobenzodiazepines and conjugates thereof |
| CN107148285B (zh) | 2014-11-25 | 2022-01-04 | Adc治疗股份有限公司 | 吡咯并苯并二氮杂䓬-抗体缀合物 |
| CA2978340C (en) | 2015-03-27 | 2024-05-28 | Regeneron Pharmaceuticals, Inc. | Maytansinoid derivatives, conjugates thereof, and methods of use |
| GB201506411D0 (en) | 2015-04-15 | 2015-05-27 | Bergenbio As | Humanized anti-axl antibodies |
| GB201506402D0 (en) | 2015-04-15 | 2015-05-27 | Berkel Patricius H C Van And Howard Philip W | Site-specific antibody-drug conjugates |
| JP6993958B2 (ja) | 2015-07-06 | 2022-02-04 | リジェネロン・ファーマシューティカルズ・インコーポレイテッド | 多重特異性抗原結合分子およびその使用 |
| MA43416A (fr) | 2015-12-11 | 2018-10-17 | Regeneron Pharma | Méthodes pour ralentir ou empêcher la croissance de tumeurs résistantes au blocage de l'egfr et/ou d'erbb3 |
| MX390630B (es) | 2016-01-25 | 2025-03-21 | Regeneron Pharma | Derivados de maitansinoide, conjugados de los mismos y metodos de uso. |
| GB201601431D0 (en) | 2016-01-26 | 2016-03-09 | Medimmune Ltd | Pyrrolobenzodiazepines |
| GB201602359D0 (en) | 2016-02-10 | 2016-03-23 | Medimmune Ltd | Pyrrolobenzodiazepine Conjugates |
| GB201602356D0 (en) | 2016-02-10 | 2016-03-23 | Medimmune Ltd | Pyrrolobenzodiazepine Conjugates |
| WO2017190079A1 (en) | 2016-04-28 | 2017-11-02 | Regeneron Pharmaceuticals, Inc. | Methods of making multispecific antigen-binding molecules |
| GB201607478D0 (en) | 2016-04-29 | 2016-06-15 | Medimmune Ltd | Pyrrolobenzodiazepine Conjugates |
| WO2018002902A1 (en) | 2016-07-01 | 2018-01-04 | Glaxosmithkline Intellectual Property (No.2) Limited | Antibody-drug conjugates and therapeutic methods using the same |
| KR102531251B1 (ko) | 2016-09-23 | 2023-05-15 | 리제너론 파아마슈티컬스, 인크. | 이특이적 항-muc16-cd3 항체 및 항-muc16 약물 접합체 |
| KR102520731B1 (ko) | 2016-09-23 | 2023-04-14 | 리제너론 파아마슈티컬스, 인크. | 항-steap2 항체, 항체-약물 컨쥬게이트, 및 steap2 및 cd3에 결합하는 이중특이적 항원-결합 분자, 및 이의 용도 |
| GB201617466D0 (en) | 2016-10-14 | 2016-11-30 | Medimmune Ltd | Pyrrolobenzodiazepine conjugates |
| CA3042428A1 (en) | 2016-11-08 | 2018-05-17 | Regeneron Pharmaceuticals, Inc. | Steroids and protein-conjugates thereof |
| TWI782930B (zh) | 2016-11-16 | 2022-11-11 | 美商再生元醫藥公司 | 抗ｍｅｔ抗體，結合ｍｅｔ之雙特異性抗原結合分子及其使用方法 |
| GB201702031D0 (en) | 2017-02-08 | 2017-03-22 | Medlmmune Ltd | Pyrrolobenzodiazepine-antibody conjugates |
| RS61795B1 (sr) | 2017-02-08 | 2021-06-30 | Adc Therapeutics Sa | Konjugati pirolobenzodiazepin antitela |
| SMT202200490T1 (it) | 2017-04-18 | 2023-01-13 | Medimmune Ltd | Coniugati di pirrolobenzodiazepina |
| WO2018193102A1 (en) | 2017-04-20 | 2018-10-25 | Adc Therapeutics Sa | Combination therapy with an anti-axl antibody-drug conjugate |
| KR20250008984A (ko) | 2017-05-18 | 2025-01-16 | 리제너론 파마슈티칼스 인코포레이티드 | 사이클로덱스트린 단백질 약물 접합체 |
| EP3625209A1 (en) | 2017-05-18 | 2020-03-25 | Regeneron Pharmaceuticals, Inc. | Bis-octahydrophenanthrene carboxamides and protein conjugates thereof |
| AU2018281280B2 (en) | 2017-06-07 | 2024-12-19 | Regeneron Pharmaceuticals, Inc. | Compositions and methods for internalizing enzymes |
| KR102442736B1 (ko) | 2017-06-14 | 2022-09-16 | 에이디씨 테라퓨틱스 에스에이 | 항-cd19 adc의 투여를 위한 투약량 체제 |
| SI3668874T1 (sl) | 2017-08-18 | 2022-04-29 | Medimmune Limited | Pirolobenzodiazepinski konjugati |
| CA3177215C (en) | 2017-09-29 | 2026-06-09 | Daiichi Sankyo Company, Limited | Antibody-pyrrolobenzodiazepine derivative conjugate |
| CA3247730A1 (en) | 2017-11-07 | 2025-10-30 | Regeneron Pharmaceuticals, Inc. | Hydrophilic linkers for antibody drug conjugates |
| MA50259A1 (fr) | 2018-01-08 | 2021-07-29 | Regeneron Pharma | Stéroïdes et leurs conjugués-anticorps |
| GB201803342D0 (en) | 2018-03-01 | 2018-04-18 | Medimmune Ltd | Methods |
| MX2020010110A (es) | 2018-03-28 | 2020-11-06 | Mitsubishi Tanabe Pharma Corp | Conjugados de farmacos de agentes de union monoclonales de cmet, y usos de los mismos. |
| GB201806022D0 (en) | 2018-04-12 | 2018-05-30 | Medimmune Ltd | Pyrrolobenzodiazepines and conjugates thereof |
| JP7328990B2 (ja) | 2018-04-30 | 2023-08-17 | リジェネロン・ファーマシューティカルズ・インコーポレイテッド | Ｈｅｒ２及び／またはａｐｌｐ２に結合する抗体及び二重特異性抗原結合分子、ならびにそれらのコンジュゲート及び使用 |
| WO2019217591A1 (en) | 2018-05-09 | 2019-11-14 | Regeneron Pharmaceuticals, Inc. | Anti-msr1 antibodies and methods of use thereof |
| EP3793591A1 (en) | 2018-05-17 | 2021-03-24 | Regeneron Pharmaceuticals, Inc. | Anti-cd63 antibodies, conjugates, and uses thereof |
| CA3120528A1 (en) | 2018-11-20 | 2020-05-28 | Regeneron Pharmaceuticals, Inc. | Bis-octahydrophenanthrene carboxamide derivatives and protein conjugates thereof for use as lxr agonists |
| WO2020132483A1 (en) | 2018-12-21 | 2020-06-25 | Regeneron Pharmaceuticals, Inc. | Rifamycin analogs and antibody-drug conjugates thereof |
| WO2020132658A2 (en) | 2018-12-21 | 2020-06-25 | Regeneron Pharmaceuticals, Inc. | Tubulysins and protein-tubulysin conjugates |
| JP2022517767A (ja) | 2019-01-08 | 2022-03-10 | レゲネロン ファーマシューティカルス，インコーポレーテッド | 無痕跡型リンカー及びそのタンパク質－コンジュゲート |
| KR20210130755A (ko) | 2019-02-21 | 2021-11-01 | 리제너론 파마슈티칼스 인코포레이티드 | 항-met 항체 및 met에 결합하는 이중특이적 항원 결합 분자를 사용하여 안구암을 치료하는 방법 |
| CN113631560B (zh) | 2019-03-15 | 2025-02-18 | 麦迪穆有限责任公司 | 氮杂环丁烷并苯并二氮杂䓬二聚体和用于治疗癌症的包含它们的缀合物 |
| CN114340684B (zh) | 2019-09-16 | 2025-09-12 | 瑞泽恩制药公司 | 用于免疫pet成像的放射性标记的met结合蛋白 |
| US11814428B2 (en) | 2019-09-19 | 2023-11-14 | Regeneron Pharmaceuticals, Inc. | Anti-PTCRA antibody-drug conjugates and uses thereof |
| MX2022008901A (es) | 2020-01-24 | 2022-08-16 | Regeneron Pharma | Conjugados de proteinas-compuestos antivirales. |
| CA3166619A1 (en) | 2020-02-28 | 2021-09-02 | Julian Andreev | Bispecific antigen binding molecules that bind her2, and methods of use thereof |
| MX2022012821A (es) | 2020-04-16 | 2022-11-07 | Regeneron Pharma | Metodos de conjugacion de diels-alder. |
| MX2022015769A (es) | 2020-06-24 | 2023-01-19 | Regeneron Pharma | Tubulisinas y conjugados de proteina-tubulisina. |
| US12605459B2 (en) | 2020-07-13 | 2026-04-21 | Regeneron Pharmaceuticals, Inc. | Protein-drug conjugates comprising camptothecin analogs and methods of use thereof |
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| US11866502B2 (en) | 2020-10-22 | 2024-01-09 | Regeneron Pharmaceuticals, Inc. | Anti-FGFR2 antibodies and methods of use thereof |
| KR20240038928A (ko) | 2021-07-28 | 2024-03-26 | 리제너론 파마슈티칼스 인코포레이티드 | 단백질-항바이러스 화합물 접합체 |
| EP4410307A4 (en) | 2021-09-30 | 2026-05-06 | Jiangsu Hengrui Pharmaceuticals Co Ltd | PYRROLO BENZODIAZEPINE DERIVATIVE AND CONJUGATE, PROCESS FOR THEIR PREPARATION AND USE |
| WO2023129518A1 (en) | 2021-12-29 | 2023-07-06 | Regeneron Pharmaceuticals, Inc. | Tubulysins and protein-tubulysin conjugates |
| MX2024008640A (es) | 2022-01-12 | 2024-07-24 | Regeneron Pharma | Analogos de camptotecina conjugados a un residuo de glutamina en una proteina y su uso. |
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| CA3243669A1 (en) | 2022-03-11 | 2023-09-14 | Regeneron Pharmaceuticals, Inc. | ANTI-GLP1R ANTIBODY-DRUG CONJUGATES INCLUDING GLP1 PEPTIDOMIMETS AND THEIR USES |
| AU2023298568A1 (en) | 2022-06-30 | 2025-01-09 | Toray Industries, Inc. | Pharmaceutical composition for cancer treatment and/or prevention |
| WO2024020164A2 (en) | 2022-07-21 | 2024-01-25 | Firefly Bio, Inc. | Glucocorticoid receptor agonists and conjugates thereof |
| EP4626553A2 (en) | 2022-11-30 | 2025-10-08 | Regeneron Pharmaceuticals, Inc. | Tlr7 agonists and antibody-drug-conjugates thereof |
| WO2024138000A1 (en) | 2022-12-21 | 2024-06-27 | Regeneron Pharmaceuticals, Inc. | Prodrugs of topoisomerase i inhibitor for adc conjugations and methods of use thereof |
| WO2024168199A1 (en) | 2023-02-09 | 2024-08-15 | Regeneron Pharmaceuticals, Inc. | Antibody-drug conjugates via inverse electron demand diels-alder reactions |
| CN121039163A (zh) | 2023-05-02 | 2025-11-28 | 瑞泽恩制药公司 | 抗人m-钙粘蛋白（cdh15）抗体、缀合物及其用于将遗传有效负载递送至肌肉细胞的用途 |
| IL325400A (en) | 2023-07-10 | 2026-02-01 | Regeneron Pharma | Anti-human CACNG1 antibody-drug conjugates and their uses |
| CN122295135A (zh) | 2023-11-03 | 2026-06-26 | 瑞泽恩制药公司 | 作为glp1r激动剂的肽酸及其抗体-药物缀合物 |
| WO2025117727A1 (en) | 2023-11-29 | 2025-06-05 | Regeneron Pharmaceuticals, Inc. | Analogs of quinoxaline/quinoline cytotoxins, linker- payloads, protein-drug conjugates, and uses thereof |
| US20260078179A1 (en) | 2024-07-18 | 2026-03-19 | Novarock Biotherapeutics, Ltd. | Cdh17 antibodies and uses thereof |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3523941A (en) | 1967-03-06 | 1970-08-11 | Hoffmann La Roche | Benzodiazepine compounds and process for their preparation |
| US3524849A (en) | 1967-10-27 | 1970-08-18 | Hoffmann La Roche | Process for the preparation of pyrrolo-benzodiazepine acrylamides and intermediates useful therein |
| US3619374A (en) | 1967-12-04 | 1971-11-09 | Hoffmann La Roche | Antibiotic production utilizing streptomyces refuineus var. thermotolerans |
| IL33558A (en) | 1968-12-30 | 1973-10-25 | Fujisawa Pharmaceutical Co | Antibiotic pyrrolo-benzodiazepine compound,its derivatives and processes for their production |
| DE1965304A1 (de) | 1968-12-30 | 1970-07-23 | Fujisawa Pharmaceutical Co | Benzdiazepinon-Verbindungen und Verfahren zu ihrer Herstellung |
| JPS6053033B2 (ja) | 1976-12-28 | 1985-11-22 | 財団法人微生物化学研究会 | 新制癌抗生物質マゼスラマイシン及びその製造方法 |
| JPS585916B2 (ja) | 1977-12-27 | 1983-02-02 | 株式会社ミドリ十字 | 新規ベンゾジアゼピン系化合物 |
| JPS5615289A (en) | 1979-07-17 | 1981-02-14 | Green Cross Corp:The | Novel benzodiazepinnbased compound 3 |
| JPS57131791A (en) | 1980-12-31 | 1982-08-14 | Fujisawa Pharmaceut Co Ltd | Benzodiazepine derivative and its preparation |
| JPS58180487A (ja) | 1982-04-16 | 1983-10-21 | Kyowa Hakko Kogyo Co Ltd | 抗生物質ｄｃ−８１およびその製造法 |
| FR2586683B1 (fr) | 1985-08-29 | 1988-07-01 | Centre Nat Rech Scient | Nouveaux derives de neothramycine, leur procede de preparation et leur application en tant que medicaments |
| FR2676230B1 (fr) | 1991-05-07 | 1993-08-27 | Centre Nat Rech Scient | Nouveaux derives de pyrrolo [1,4]-benzodiazepines, leur procede de preparation et medicaments les contenant. |
| GB9205051D0 (en) | 1992-03-09 | 1992-04-22 | Cancer Res Campaign Tech | Pyrrolobenzodiazepine derivatives,their preparation,and compositions containing them |
| FR2696176B1 (fr) | 1992-09-28 | 1994-11-10 | Synthelabo | Dérivés de pipéridine, leur préparation et leur application en thérapeutique. |
| GB9818732D0 (en) | 1998-08-27 | 1998-10-21 | Univ Portsmouth | Collection of compounds |
| ES2260570T3 (es) | 1998-08-27 | 2006-11-01 | Spirogen Limited | Pirrolobenziodiazepinas dimericas. |
| GB9818730D0 (en) | 1998-08-27 | 1998-10-21 | Univ Portsmouth | Collections of compounds |
| GB9818731D0 (en) | 1998-08-27 | 1998-10-21 | Univ Portsmouth | Compounds |
| US6909006B1 (en) | 1999-08-27 | 2005-06-21 | Spirogen Limited | Cyclopropylindole derivatives |
| US6660856B2 (en) | 2002-03-08 | 2003-12-09 | Kaohsiung Medical University | Synthesis of pyrrolo[2,1-c][1,4]benzodiazepine analogues |
| US20040138269A1 (en) | 2002-10-11 | 2004-07-15 | Sugen, Inc. | Substituted pyrroles as kinase inhibitors |
| GB0226593D0 (en) | 2002-11-14 | 2002-12-24 | Consultants Ltd | Compounds |
| GB0321295D0 (en) | 2003-09-11 | 2003-10-15 | Spirogen Ltd | Synthesis of protected pyrrolobenzodiazepines |
| AU2004284075A1 (en) | 2003-10-22 | 2005-05-06 | Government Of The United States Of America, Represented By The Secretary, Department Of Health And Human Services | Pyrrolobenzodiazepine derivatives, compositions comprising the same and methods related thereto |
| GB0416511D0 (en) | 2003-10-22 | 2004-08-25 | Spirogen Ltd | Pyrrolobenzodiazepines |
| ES2398975T3 (es) | 2004-03-01 | 2013-03-25 | Spirogen Sàrl | Derivados de 11-hidroxi-5H-pirrolo[2,1-c][1,4]benzodiazepin-5-ona como intermedios clave para la preparación de pirrolobenzodiazepinas sustituidas en C2 |
| GB0404577D0 (en) | 2004-03-01 | 2004-04-07 | Spirogen Ltd | Pyrrolobenzodiazepines |
| GB0404574D0 (en) | 2004-03-01 | 2004-04-07 | Spirogen Ltd | Amino acids |
| GB0404578D0 (en) | 2004-03-01 | 2004-04-07 | Spirogen Ltd | Pyrrolobenzodiazepines |
| EP1723152B1 (en) | 2004-03-09 | 2015-02-11 | Spirogen Sàrl | Pyrrolobenzodiazepines |
| GB0410725D0 (en) | 2004-05-13 | 2004-06-16 | Spirogen Ltd | Pyrrolobenzodiazepine therapeutic agents |
| ES2338696T3 (es) | 2005-04-21 | 2010-05-11 | Spirogen Limited | Pirrolobenzodiazepinas. |
| DE602006006199D1 (de) | 2005-10-05 | 2009-05-20 | Spirogen Ltd | 4-ä4-(5-oxo-2,3,5,11a-tetrahydro-5h-pyrrolo ä2, 1-cüä1,4übenzodiazepin-8-yloxy)-butyrylaminoü-1h-pyrrol-2-carbonsäurealkylesterderivate und verwandte verbindung zur behandlung einer proliferativen erkrankung |
| JP2008050321A (ja) | 2006-08-28 | 2008-03-06 | Univ Kanagawa | 光分解性カップリング剤 |
| GB0813432D0 (en) | 2008-07-22 | 2008-08-27 | Spirogen Ltd | Pyrrolobenzodiazepines |
| GB0819095D0 (en) * | 2008-10-17 | 2008-11-26 | Spirogen Ltd | Pyrrolobenzodiazepines |
| GB201006340D0 (en) | 2010-04-15 | 2010-06-02 | Spirogen Ltd | Synthesis method and intermediates |
-
2012
- 2012-10-12 JP JP2014535096A patent/JP6166728B2/ja active Active
- 2012-10-12 EP EP12772781.6A patent/EP2751076B1/en active Active
- 2012-10-12 EA EA201490550A patent/EA029046B1/ru unknown
- 2012-10-12 CN CN201280061966.5A patent/CN104011018B/zh active Active
- 2012-10-12 BR BR112014009070-0A patent/BR112014009070B1/pt active IP Right Grant
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- 2012-10-12 US US14/351,166 patent/US9102704B2/en active Active
- 2012-10-12 CA CA2850096A patent/CA2850096C/en active Active
Non-Patent Citations (1)
| Title |
|---|
| KANG G.-D. ET AL.: "Synthesis of a novel C2-aryl substituted 1,2-unsaturated pyrrolobenzodiazepine", CHEMICAL COMMUNICATIONS - CHEMCOM; [6015D], vol. 14, 11 June 2003 (2003-06-11), pages 1688, 1689, XP002329274, ROYAL SOCIETY OF CHEMISTRY, LONDON; GB, ISSN: 1359-7345, DOI: 10.1039/B303274D Scheme 2; page 1688; compounds 6, 8-13 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2751076B1 (en) | 2018-04-25 |
| JP6166728B2 (ja) | 2017-07-19 |
| AU2012322933B2 (en) | 2017-02-02 |
| CN104011018B (zh) | 2016-12-14 |
| BR112014009070A2 (pt) | 2017-04-18 |
| JP2015502331A (ja) | 2015-01-22 |
| EA201490550A1 (ru) | 2014-09-30 |
| AU2012322933A1 (en) | 2014-05-29 |
| WO2013053872A1 (en) | 2013-04-18 |
| EP2751076A1 (en) | 2014-07-09 |
| CA2850096A1 (en) | 2013-04-18 |
| CA2850096C (en) | 2018-07-03 |
| US9102704B2 (en) | 2015-08-11 |
| BR112014009070B1 (pt) | 2021-11-23 |
| US20140275522A1 (en) | 2014-09-18 |
| CN104011018A (zh) | 2014-08-27 |
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