CN104540827B - 吡咯并苯并二氮杂卓 - Google Patents
吡咯并苯并二氮杂卓 Download PDFInfo
- Publication number
- CN104540827B CN104540827B CN201380035161.8A CN201380035161A CN104540827B CN 104540827 B CN104540827 B CN 104540827B CN 201380035161 A CN201380035161 A CN 201380035161A CN 104540827 B CN104540827 B CN 104540827B
- Authority
- CN
- China
- Prior art keywords
- nme
- alkyl
- group
- compound
- phenyl
- 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.)
- Expired - Fee Related
Links
- 0 CCNC1(*)[C@@](C)CC1 Chemical compound CCNC1(*)[C@@](C)CC1 0.000 description 5
- CAIJLZGQTNHYPU-UHFFFAOYSA-N CC(C)(C)OC(Nc(cc1)ccc1-c1c[n](C)c(C(OC)=O)c1)=O Chemical compound CC(C)(C)OC(Nc(cc1)ccc1-c1c[n](C)c(C(OC)=O)c1)=O CAIJLZGQTNHYPU-UHFFFAOYSA-N 0.000 description 1
- HHFFELUPDFMJLY-UHFFFAOYSA-N CC1=C2C(C(OC)=C)=NC(NC(c3cc(-c(cc4)ccc4N)c[n]3C)=C)=CC12 Chemical compound CC1=C2C(C(OC)=C)=NC(NC(c3cc(-c(cc4)ccc4N)c[n]3C)=C)=CC12 HHFFELUPDFMJLY-UHFFFAOYSA-N 0.000 description 1
- HUKQFKKFOGVZGH-UHFFFAOYSA-N C[n]1c(C(C(Cl)(Cl)Cl)=O)cc(Br)c1 Chemical compound C[n]1c(C(C(Cl)(Cl)Cl)=O)cc(Br)c1 HUKQFKKFOGVZGH-UHFFFAOYSA-N 0.000 description 1
- XYZFZMSLKMPMGW-UHFFFAOYSA-N C[n]1c(C(OC)=O)cc(Br)c1 Chemical compound C[n]1c(C(OC)=O)cc(Br)c1 XYZFZMSLKMPMGW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261640316P | 2012-04-30 | 2012-04-30 | |
| US61/640,316 | 2012-04-30 | ||
| PCT/GB2013/051097 WO2013164592A1 (en) | 2012-04-30 | 2013-04-30 | Pyrrolobenzodiazepines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104540827A CN104540827A (zh) | 2015-04-22 |
| CN104540827B true CN104540827B (zh) | 2018-03-23 |
Family
ID=48289484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380035161.8A Expired - Fee Related CN104540827B (zh) | 2012-04-30 | 2013-04-30 | 吡咯并苯并二氮杂卓 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US9321774B2 (enExample) |
| EP (1) | EP2855481A1 (enExample) |
| JP (1) | JP6125614B2 (enExample) |
| KR (1) | KR101960130B1 (enExample) |
| CN (1) | CN104540827B (enExample) |
| AU (1) | AU2013255612B2 (enExample) |
| BR (1) | BR112014027190B1 (enExample) |
| CA (1) | CA2872205C (enExample) |
| HK (1) | HK1208217A1 (enExample) |
| IN (1) | IN2014MN02175A (enExample) |
| MX (1) | MX2014013144A (enExample) |
| NZ (1) | NZ701478A (enExample) |
| WO (1) | WO2013164592A1 (enExample) |
| ZA (1) | ZA201408043B (enExample) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0819095D0 (en) | 2008-10-17 | 2008-11-26 | Spirogen Ltd | Pyrrolobenzodiazepines |
| CN102971329B (zh) | 2010-04-15 | 2016-06-29 | 麦迪穆有限责任公司 | 用于治疗增殖性疾病的吡咯并苯并二氮杂卓 |
| NZ602932A (en) | 2010-04-15 | 2014-08-29 | Seattle Genetics Inc | Targeted pyrrolobenzodiazapine conjugates |
| CN103987718A (zh) | 2011-09-20 | 2014-08-13 | 斯皮罗根有限公司 | 作为非对称二聚体pbd化合物用于内含在靶向结合物中的吡咯并苯并二氮杂卓 |
| US9388187B2 (en) | 2011-10-14 | 2016-07-12 | Medimmune Limited | Pyrrolobenzodiazepines |
| JP6393617B2 (ja) | 2011-10-14 | 2018-09-19 | シアトル ジェネティクス,インコーポレーテッド | ピロロベンゾジアゼピンおよび標的コンジュゲート |
| CA2850103C (en) | 2011-10-14 | 2019-09-10 | Spirogen Sarl | Pyrrolobenzodiazepines |
| CA2850375C (en) | 2011-10-14 | 2019-07-02 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines and targeted conjugates |
| HUE045435T2 (hu) | 2012-10-12 | 2019-12-30 | Medimmune Ltd | Pirrolobenzodiazepinek és konjugátumaik |
| CA2885305C (en) | 2012-10-12 | 2019-11-12 | Spirogen Sarl | Synthesis and intermediates of pyrrolobenzodiazepine derivatives for conjugation |
| HRP20182129T1 (hr) | 2012-10-12 | 2019-02-08 | Adc Therapeutics Sa | Konjugati protutijelo - pirolobenzodiazepin |
| WO2014057073A1 (en) | 2012-10-12 | 2014-04-17 | Spirogen Sàrl | Pyrrolobenzodiazepines and conjugates thereof |
| AU2013366493B2 (en) | 2012-12-21 | 2017-08-24 | Medimmune Limited | Pyrrolobenzodiazepines and conjugates thereof |
| US9567340B2 (en) | 2012-12-21 | 2017-02-14 | Medimmune Limited | Unsymmetrical pyrrolobenzodiazepines-dimers for use in the treatment of proliferative and autoimmune diseases |
| CA2904044C (en) | 2013-03-13 | 2020-03-31 | Medimmune Limited | Pyrrolobenzodiazepines and conjugates thereof |
| CN105307685B (zh) | 2013-03-13 | 2019-03-08 | 麦迪穆有限责任公司 | 吡咯并苯并二氮杂卓和其结合物 |
| 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 |
| GB201416112D0 (en) | 2014-09-12 | 2014-10-29 | Medimmune Ltd | Pyrrolobenzodiazepines and conjugates thereof |
| EP3223854A1 (en) | 2014-11-25 | 2017-10-04 | ADC Therapeutics SA | Pyrrolobenzodiazepine-antibody conjugates |
| GB201506402D0 (en) | 2015-04-15 | 2015-05-27 | Berkel Patricius H C Van And Howard Philip W | Site-specific antibody-drug conjugates |
| GB201506411D0 (en) | 2015-04-15 | 2015-05-27 | Bergenbio As | Humanized anti-axl antibodies |
| GB201521709D0 (en) * | 2015-12-09 | 2016-01-20 | Kings College London And Sec Dep For Health The | PBD Antibacterial agents |
| GB201601431D0 (en) | 2016-01-26 | 2016-03-09 | Medimmune Ltd | Pyrrolobenzodiazepines |
| GB201602356D0 (en) | 2016-02-10 | 2016-03-23 | Medimmune Ltd | Pyrrolobenzodiazepine Conjugates |
| GB201602359D0 (en) | 2016-02-10 | 2016-03-23 | Medimmune Ltd | Pyrrolobenzodiazepine Conjugates |
| GB201607478D0 (en) | 2016-04-29 | 2016-06-15 | Medimmune Ltd | Pyrrolobenzodiazepine Conjugates |
| 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 |
| US10526294B2 (en) | 2016-06-24 | 2020-01-07 | Mersana Therapeutics, Inc. | Pyrrolobenzodiazepines and conjugates thereof |
| GB201617466D0 (en) | 2016-10-14 | 2016-11-30 | Medimmune Ltd | Pyrrolobenzodiazepine conjugates |
| KR20200032243A (ko) | 2017-02-08 | 2020-03-25 | 에이디씨 테라퓨틱스 에스에이 | 피롤로벤조디아제핀-항체 컨주게이트 |
| GB201702031D0 (en) | 2017-02-08 | 2017-03-22 | Medlmmune Ltd | Pyrrolobenzodiazepine-antibody conjugates |
| SI3612537T1 (sl) | 2017-04-18 | 2022-10-28 | Medimmune Limited | Konjugati pirolobenzodiazepina |
| EP3612234B1 (en) | 2017-04-20 | 2024-03-13 | ADC Therapeutics SA | Combination therapy with an anti-axl antibody-drug conjugate |
| KR102442736B1 (ko) | 2017-06-14 | 2022-09-16 | 에이디씨 테라퓨틱스 에스에이 | 항-cd19 adc의 투여를 위한 투약량 체제 |
| CN111065638B (zh) | 2017-08-18 | 2021-04-09 | 麦迪穆有限责任公司 | 吡咯并苯并二氮杂䓬缀合物 |
| IL301638B2 (en) | 2017-09-29 | 2024-09-01 | Daiichi Sankyo Co Ltd | Antibody-pyrrolobenzodiazepine derivative conjugate |
| EP3717021A1 (en) | 2017-11-27 | 2020-10-07 | Mersana Therapeutics, Inc. | Pyrrolobenzodiazepine antibody conjugates |
| GB201803342D0 (en) | 2018-03-01 | 2018-04-18 | Medimmune Ltd | Methods |
| GB201806022D0 (en) | 2018-04-12 | 2018-05-30 | Medimmune Ltd | Pyrrolobenzodiazepines and conjugates thereof |
| GB201900929D0 (en) * | 2019-01-23 | 2019-03-13 | King S College London | Nf-kappa b inhibitors |
| IL286326B2 (en) | 2019-03-15 | 2025-10-01 | Medimmune Ltd | Azatidobenzodiazepine dimers and conjugates containing them for use in the treatment of cancer |
| KR20210086557A (ko) | 2019-12-31 | 2021-07-08 | 주식회사 레고켐 바이오사이언스 | 피롤로벤조디아제핀 유도체 및 이의 리간드-링커 접합체 |
| GB2597532A (en) | 2020-07-28 | 2022-02-02 | Femtogenix Ltd | Cytotoxic compounds |
| AU2023298568A1 (en) | 2022-06-30 | 2025-01-09 | Toray Industries, Inc. | Pharmaceutical composition for cancer treatment and/or prevention |
| AU2023393382A1 (en) | 2022-12-14 | 2025-06-19 | Pheon Therapeutics Ltd | Cytotoxic compounds |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005085177A2 (en) * | 2004-03-01 | 2005-09-15 | Spirogen Limited | Biaryl amino acids and their use in dna binding oligomers |
| WO2007039752A1 (en) * | 2005-10-05 | 2007-04-12 | Spirogen Limited | Alkyl 4- [4- (5-oxo-2, 3, 5, 11a-tetrahyd0-5h-pyrr0l0 [2, 1-c] [1, 4] benzodiazepine-8-yloxy) -butyrylamino]-1h-pyrrole-2-carboxylate derivatives and related compounds for the treatment of a proliferative disease |
| WO2009060208A1 (en) * | 2007-11-09 | 2009-05-14 | Spirogen Limited | Pyrrolobenzodiazepines |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5569587A (en) | 1978-11-17 | 1980-05-26 | Meiji Seika Kaisha Ltd | Novel antibiotic neothramycin derivative and its preparation |
| JPS5615289A (en) | 1979-07-17 | 1981-02-14 | Green Cross Corp:The | Novel benzodiazepinnbased compound 3 |
| 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 |
| US5229490A (en) | 1987-05-06 | 1993-07-20 | The Rockefeller University | Multiple antigen peptide system |
| US6187797B1 (en) | 1996-12-23 | 2001-02-13 | Dupont Pharmaceuticals Company | Phenyl-isoxazoles as factor XA Inhibitors |
| DE69720773T2 (de) | 1996-12-23 | 2004-01-29 | Bristol Myers Squibb Pharma Co | SAUERSTOFF ODER SCHWEFEL ENTHALTENDE 5-GLIEDRIGE HETEROAROMATISHE DERIVATIVE ALS FACTOR Xa HEMMER |
| WO1999046244A1 (en) | 1998-03-12 | 1999-09-16 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (ptpases) |
| GB9818731D0 (en) | 1998-08-27 | 1998-10-21 | Univ Portsmouth | Compounds |
| GB9818732D0 (en) | 1998-08-27 | 1998-10-21 | Univ Portsmouth | Collection of compounds |
| DK1193270T3 (da) | 1998-08-27 | 2003-09-15 | Spirogen Ltd | Pyrrolobenzodiazepiner |
| GB9818730D0 (en) | 1998-08-27 | 1998-10-21 | Univ Portsmouth | Collections of compounds |
| US6909006B1 (en) | 1999-08-27 | 2005-06-21 | Spirogen Limited | Cyclopropylindole derivatives |
| MXPA02005937A (es) | 1999-12-20 | 2004-08-12 | Univ North Carolina | Compuestos de diamina como aglutinantes de surco menor. |
| WO2002062755A2 (en) * | 2000-12-27 | 2002-08-15 | Genelabs Technologies, Inc. | Polyamide analogs as dna minor groove binders |
| US6777425B2 (en) * | 2001-06-13 | 2004-08-17 | Genesoft Pharmaceuticals, Inc. | Isoquinoline compounds having antiinfective activity |
| JP2005502703A (ja) * | 2001-09-07 | 2005-01-27 | ザ スクリプス リサーチ インスティテュート | Cc−1065およびデュオカルマイシンのcbi類似体 |
| 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 |
| WO2005032594A2 (en) * | 2003-10-03 | 2005-04-14 | The Government Of The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Alkylators linked to polyamides as dna binding agents |
| GB0404578D0 (en) | 2004-03-01 | 2004-04-07 | Spirogen Ltd | Pyrrolobenzodiazepines |
| GB0404577D0 (en) | 2004-03-01 | 2004-04-07 | Spirogen Ltd | Pyrrolobenzodiazepines |
| CA2558195C (en) | 2004-03-01 | 2012-11-06 | Spirogen Limited | 11-hydroxy-5h-pyrrolo[2,1-c][1,4]benzodiazepin-5-one derivatives as key intermediates for the preparation of c2 substituted pyrrolobenzodiazepines |
| JP5166861B2 (ja) | 2004-03-09 | 2013-03-21 | スピロゲン リミティッド | ピロロベンゾジアゼピン |
| GB0410725D0 (en) | 2004-05-13 | 2004-06-16 | Spirogen Ltd | Pyrrolobenzodiazepine therapeutic agents |
| AU2006238686B2 (en) | 2005-04-21 | 2011-10-06 | Medimmune Limited | Pyrrolobenzodiazepines |
| WO2008060208A1 (en) | 2006-11-16 | 2008-05-22 | Telefonaktiebolaget L M Ericsson (Publ) | Gateway selection mechanism |
| GB0813432D0 (en) | 2008-07-22 | 2008-08-27 | Spirogen Ltd | Pyrrolobenzodiazepines |
| GB0819095D0 (en) | 2008-10-17 | 2008-11-26 | Spirogen Ltd | Pyrrolobenzodiazepines |
-
2013
- 2013-04-30 AU AU2013255612A patent/AU2013255612B2/en not_active Ceased
- 2013-04-30 CN CN201380035161.8A patent/CN104540827B/zh not_active Expired - Fee Related
- 2013-04-30 BR BR112014027190-9A patent/BR112014027190B1/pt not_active IP Right Cessation
- 2013-04-30 WO PCT/GB2013/051097 patent/WO2013164592A1/en not_active Ceased
- 2013-04-30 MX MX2014013144A patent/MX2014013144A/es unknown
- 2013-04-30 HK HK15108789.1A patent/HK1208217A1/xx unknown
- 2013-04-30 US US14/397,843 patent/US9321774B2/en not_active Expired - Fee Related
- 2013-04-30 JP JP2015509487A patent/JP6125614B2/ja active Active
- 2013-04-30 NZ NZ701478A patent/NZ701478A/en not_active IP Right Cessation
- 2013-04-30 EP EP13720502.7A patent/EP2855481A1/en not_active Withdrawn
- 2013-04-30 IN IN2175MUN2014 patent/IN2014MN02175A/en unknown
- 2013-04-30 CA CA2872205A patent/CA2872205C/en not_active Expired - Fee Related
- 2013-04-30 KR KR1020147032596A patent/KR101960130B1/ko not_active Expired - Fee Related
-
2014
- 2014-11-04 ZA ZA2014/08043A patent/ZA201408043B/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005085177A2 (en) * | 2004-03-01 | 2005-09-15 | Spirogen Limited | Biaryl amino acids and their use in dna binding oligomers |
| WO2007039752A1 (en) * | 2005-10-05 | 2007-04-12 | Spirogen Limited | Alkyl 4- [4- (5-oxo-2, 3, 5, 11a-tetrahyd0-5h-pyrr0l0 [2, 1-c] [1, 4] benzodiazepine-8-yloxy) -butyrylamino]-1h-pyrrole-2-carboxylate derivatives and related compounds for the treatment of a proliferative disease |
| WO2009060208A1 (en) * | 2007-11-09 | 2009-05-14 | Spirogen Limited | Pyrrolobenzodiazepines |
Non-Patent Citations (3)
| Title |
|---|
| Biaryl polyamides as a new class of DNA quadruplex-binding ligands;Khondaker M. Rahman et al.;《Chem. Commun.》;20090605;第4097-4099页,尤其是摘要、Figure 1 * |
| GC-Targeted C8-Linked Pyrrolobenzodiazepine−Biaryl Conjugates with Femtomolar in Vitro Cytotoxicity and in Vivo Antitumor Activity in Mouse Models;Khondaker M. Rahman et al.;《Journal of Medicinal Chemistry》;20130321;第56卷;第2911−2935页,摘要,第2915页Figure 4,第2921页Scheme 1 * |
| Novel C8-linked pyrrolobenzodiazepine (PBD)–heterocycle conjugates that recognize DNA sequences containing an inverted CCAAT box;Federico Brucoli et al.;《Bioorganic & Medicinal Chemistry Letters》;20110420;第21卷;第3780-3783页,摘要,第3781页Figure 1、Scheme 1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| NZ701478A (en) | 2016-08-26 |
| CA2872205C (en) | 2020-07-21 |
| CA2872205A1 (en) | 2013-11-07 |
| US20150126495A1 (en) | 2015-05-07 |
| US9321774B2 (en) | 2016-04-26 |
| JP6125614B2 (ja) | 2017-05-10 |
| BR112014027190A2 (pt) | 2017-06-27 |
| JP2015516987A (ja) | 2015-06-18 |
| AU2013255612A1 (en) | 2014-11-20 |
| IN2014MN02175A (enExample) | 2015-08-28 |
| BR112014027190B1 (pt) | 2020-03-03 |
| MX2014013144A (es) | 2015-05-11 |
| HK1208217A1 (en) | 2016-02-26 |
| ZA201408043B (en) | 2017-08-30 |
| AU2013255612B2 (en) | 2017-06-22 |
| KR101960130B1 (ko) | 2019-03-19 |
| EP2855481A1 (en) | 2015-04-08 |
| CN104540827A (zh) | 2015-04-22 |
| WO2013164592A1 (en) | 2013-11-07 |
| KR20150014935A (ko) | 2015-02-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C41 | Transfer of patent application or patent right or utility model | ||
| CB02 | Change of applicant information |
Address after: London, England Applicant after: UCL BUSINESS PLC Applicant after: SPIROGEN Ltd. Address before: London, England Applicant before: UCL BUSINESS PLC Applicant before: Spirogen Ltd. |
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Effective date of registration: 20160127 Address after: London, England Applicant after: UCL BUSINESS PLC Applicant after: MEDIMMUNE LTD. Address before: London, England Applicant before: UCL BUSINESS PLC Applicant before: Spirogen Ltd. |
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| CF01 | Termination of patent right due to non-payment of annual fee | ||
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