GB1299198A - Pyrrolobenzodiazepinone derivatives - Google Patents
Pyrrolobenzodiazepinone derivativesInfo
- Publication number
- GB1299198A GB1299198A GB62863/69A GB6286369A GB1299198A GB 1299198 A GB1299198 A GB 1299198A GB 62863/69 A GB62863/69 A GB 62863/69A GB 6286369 A GB6286369 A GB 6286369A GB 1299198 A GB1299198 A GB 1299198A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- formula
- aryl
- alkoxy
- solvent
- 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
Links
- VRQOSIAJWZNUSL-UHFFFAOYSA-N 2h-pyrrolo[2,3-i][1,2]benzodiazepin-3-one Chemical class C12=NNC(=O)C=CC2=CC=C2C1=CC=N2 VRQOSIAJWZNUSL-UHFFFAOYSA-N 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 22
- 125000003545 alkoxy group Chemical group 0.000 abstract 5
- 239000002904 solvent Substances 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 2
- 230000001476 alcoholic effect Effects 0.000 abstract 2
- 125000005129 aryl carbonyl group Chemical group 0.000 abstract 2
- 230000000694 effects Effects 0.000 abstract 2
- 238000000855 fermentation Methods 0.000 abstract 2
- 230000004151 fermentation Effects 0.000 abstract 2
- 238000002955 isolation Methods 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 241000894006 Bacteria Species 0.000 abstract 1
- 239000005909 Kieselgur Substances 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 241000958303 Streptomyces achromogenes Species 0.000 abstract 1
- 241001655322 Streptomycetales Species 0.000 abstract 1
- 241000700605 Viruses Species 0.000 abstract 1
- 239000002168 alkylating agent Substances 0.000 abstract 1
- 229940100198 alkylating agent Drugs 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 125000005265 dialkylamine group Chemical group 0.000 abstract 1
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 238000010828 elution Methods 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000003495 polar organic solvent Substances 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000000741 silica gel Substances 0.000 abstract 1
- 229910002027 silica gel Inorganic materials 0.000 abstract 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 abstract 1
- 235000012239 silicon dioxide Nutrition 0.000 abstract 1
- 238000001179 sorption measurement Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 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
-
- 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
- C07D487/06—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8368 | 1968-12-30 | ||
| JP44050780A JPS4843755B1 (enrdf_load_stackoverflow) | 1969-06-26 | 1969-06-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1299198A true GB1299198A (en) | 1972-12-06 |
Family
ID=26332992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB62863/69A Expired GB1299198A (en) | 1968-12-30 | 1969-12-24 | Pyrrolobenzodiazepinone derivatives |
Country Status (6)
| Country | Link |
|---|---|
| ES (1) | ES375013A1 (enrdf_load_stackoverflow) |
| FI (1) | FI46259C (enrdf_load_stackoverflow) |
| GB (1) | GB1299198A (enrdf_load_stackoverflow) |
| IE (1) | IE33906B1 (enrdf_load_stackoverflow) |
| IL (1) | IL33558A (enrdf_load_stackoverflow) |
| RO (1) | RO55813A (enrdf_load_stackoverflow) |
Cited By (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0101924A1 (en) * | 1982-07-26 | 1984-03-07 | Bristol-Myers Company | Antitumor antibiotics |
| WO2000012508A3 (en) * | 1998-08-27 | 2000-09-21 | Univ Portsmouth | Pyrrolbenzodiazepines |
| US6608192B1 (en) | 1998-08-27 | 2003-08-19 | Spirogen Limited | Collections of compounds |
| US6747144B1 (en) | 1998-08-27 | 2004-06-08 | Spirogen Limited | Collections of compounds |
| US6909006B1 (en) | 1999-08-27 | 2005-06-21 | Spirogen Limited | Cyclopropylindole derivatives |
| US7407951B2 (en) | 2002-11-14 | 2008-08-05 | Spirogen Limited | Pyrrolobenzodiazepines |
| US7429658B2 (en) | 2003-09-11 | 2008-09-30 | Spirogen Limited | Synthesis of protected pyrrolobenzodiazepines |
| US7528126B2 (en) | 2004-03-09 | 2009-05-05 | Spirogen Limited | Pyrrolobenzodiazepines |
| US7557099B2 (en) | 2004-03-01 | 2009-07-07 | Spirogen Limited | Pyrrolobenzodiazepines as key intermediates in the synthesis of dimeric cytotoxic pyrrolobenzodiazepines |
| US7741319B2 (en) | 2004-03-01 | 2010-06-22 | 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 |
| US8592576B2 (en) | 2008-10-17 | 2013-11-26 | Spirogen Sarl | Unsymmetrical pyrrolobenzodiazepine-dimers for treatment of proliferative diseases |
| US8697688B2 (en) | 2010-04-15 | 2014-04-15 | Seattle Genetics Inc. | Pyrrolobenzodiazepines used to treat proliferative diseases |
| US8829184B2 (en) | 2010-04-15 | 2014-09-09 | Spirogen Sarl | Intermediates useful for the synthesis of pyrrolobenzodiazepines |
| US20140286970A1 (en) | 2011-10-14 | 2014-09-25 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines and targeted conjugates |
| US9102704B2 (en) | 2011-10-14 | 2015-08-11 | Spirogen Sarl | Synthesis method and intermediates useful in the preparation of pyrrolobenzodiazepines |
| US9242013B2 (en) | 2010-04-15 | 2016-01-26 | Seattle Genetics Inc. | Targeted pyrrolobenzodiazapine conjugates |
| US9387259B2 (en) | 2011-10-14 | 2016-07-12 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines and targeted conjugates |
| US9388187B2 (en) | 2011-10-14 | 2016-07-12 | Medimmune Limited | Pyrrolobenzodiazepines |
| US9399641B2 (en) | 2011-09-20 | 2016-07-26 | Medimmune Limited | Pyrrolobenzodiazepines as unsymmetrical dimeric PBD compounds for inclusion in targeted conjugates |
| US9399073B2 (en) | 2011-10-14 | 2016-07-26 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines |
| US9415117B2 (en) | 2012-10-12 | 2016-08-16 | Medimmune Limited | Pyrrolobenzodiazepines and conjugates thereof |
| US9745303B2 (en) | 2012-10-12 | 2017-08-29 | Medimmune Limited | Synthesis and intermediates of pyrrolobenzodiazepine derivatives for conjugation |
| US9919056B2 (en) | 2012-10-12 | 2018-03-20 | Adc Therapeutics S.A. | Pyrrolobenzodiazepine-anti-CD22 antibody conjugates |
| US9931415B2 (en) | 2012-10-12 | 2018-04-03 | Medimmune Limited | Pyrrolobenzodiazepine-antibody conjugates |
| US9931414B2 (en) | 2012-10-12 | 2018-04-03 | Medimmune Limited | Pyrrolobenzodiazepine-antibody conjugates |
| US9950078B2 (en) | 2013-10-11 | 2018-04-24 | Medimmune Limited | Pyrrolobenzodiazepine-antibody conjugates |
| US9956299B2 (en) | 2013-10-11 | 2018-05-01 | Medimmune Limited | Pyrrolobenzodiazepine—antibody conjugates |
| US9956298B2 (en) | 2013-10-11 | 2018-05-01 | Medimmune Limited | Pyrrolobenzodiazepines and conjugates thereof |
| US10010624B2 (en) | 2013-10-11 | 2018-07-03 | Medimmune Limited | Pyrrolobenzodiazepine-antibody conjugates |
| US10335497B2 (en) | 2012-10-12 | 2019-07-02 | Medimmune Limited | Pyrrolobenzodiazepines and conjugates thereof |
| US10392393B2 (en) | 2016-01-26 | 2019-08-27 | Medimmune Limited | Pyrrolobenzodiazepines |
| US10420777B2 (en) | 2014-09-12 | 2019-09-24 | Medimmune Limited | Pyrrolobenzodiazepines and conjugates thereof |
| US10543279B2 (en) | 2016-04-29 | 2020-01-28 | Medimmune Limited | Pyrrolobenzodiazepine conjugates and their use for the treatment of cancer |
| US10544223B2 (en) | 2017-04-20 | 2020-01-28 | Adc Therapeutics Sa | Combination therapy with an anti-axl antibody-drug conjugate |
| US10695439B2 (en) | 2016-02-10 | 2020-06-30 | Medimmune Limited | Pyrrolobenzodiazepine conjugates |
| US10695433B2 (en) | 2012-10-12 | 2020-06-30 | Medimmune Limited | Pyrrolobenzodiazepine-antibody conjugates |
| US10736903B2 (en) | 2012-10-12 | 2020-08-11 | Medimmune Limited | Pyrrolobenzodiazepine-anti-PSMA antibody conjugates |
| US10751346B2 (en) | 2012-10-12 | 2020-08-25 | Medimmune Limited | Pyrrolobenzodiazepine—anti-PSMA antibody conjugates |
| US10780096B2 (en) | 2014-11-25 | 2020-09-22 | Adc Therapeutics Sa | Pyrrolobenzodiazepine-antibody conjugates |
| US10799595B2 (en) | 2016-10-14 | 2020-10-13 | Medimmune Limited | Pyrrolobenzodiazepine conjugates |
| US11059893B2 (en) | 2015-04-15 | 2021-07-13 | Bergenbio Asa | Humanized anti-AXL antibodies |
| US11160872B2 (en) | 2017-02-08 | 2021-11-02 | Adc Therapeutics Sa | Pyrrolobenzodiazepine-antibody conjugates |
| US11318211B2 (en) | 2017-06-14 | 2022-05-03 | Adc Therapeutics Sa | Dosage regimes for the administration of an anti-CD19 ADC |
| US11352324B2 (en) | 2018-03-01 | 2022-06-07 | Medimmune Limited | Methods |
| US11370801B2 (en) | 2017-04-18 | 2022-06-28 | Medimmune Limited | Pyrrolobenzodiazepine conjugates |
| US11517626B2 (en) | 2016-02-10 | 2022-12-06 | Medimmune Limited | Pyrrolobenzodiazepine antibody conjugates |
| US11524969B2 (en) | 2018-04-12 | 2022-12-13 | Medimmune Limited | Pyrrolobenzodiazepines and conjugates thereof as antitumour agents |
| US11612665B2 (en) | 2017-02-08 | 2023-03-28 | Medimmune Limited | Pyrrolobenzodiazepine-antibody conjugates |
| US11649250B2 (en) | 2017-08-18 | 2023-05-16 | Medimmune Limited | Pyrrolobenzodiazepine conjugates |
| US11702473B2 (en) | 2015-04-15 | 2023-07-18 | Medimmune Limited | Site-specific antibody-drug conjugates |
| US12209099B2 (en) | 2019-03-15 | 2025-01-28 | Medimmune Limited | Azetidobenzodiazepine dimers and conjugates comprising them for use in the treatment of cancer |
-
1969
- 1969-12-17 IL IL33558A patent/IL33558A/xx unknown
- 1969-12-22 FI FI693710A patent/FI46259C/fi active
- 1969-12-24 GB GB62863/69A patent/GB1299198A/en not_active Expired
- 1969-12-29 ES ES375013A patent/ES375013A1/es not_active Expired
- 1969-12-30 IE IE1726/69A patent/IE33906B1/xx unknown
- 1969-12-30 RO RO62025A patent/RO55813A/ro unknown
Cited By (80)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0101924A1 (en) * | 1982-07-26 | 1984-03-07 | Bristol-Myers Company | Antitumor antibiotics |
| US7704924B2 (en) | 1998-08-27 | 2010-04-27 | Spirogen Limited | Library of compounds comprising pyrrolobenzodiazepine moieties |
| WO2000012508A3 (en) * | 1998-08-27 | 2000-09-21 | Univ Portsmouth | Pyrrolbenzodiazepines |
| EP1193270A3 (en) * | 1998-08-27 | 2002-04-17 | Spirogen Limited | Pyrrolobenzodiazepines |
| US6608192B1 (en) | 1998-08-27 | 2003-08-19 | Spirogen Limited | Collections of compounds |
| EP1413582A1 (en) * | 1998-08-27 | 2004-04-28 | Spirogen Limited | Dimeric pyrrolobenzodiazepines |
| US6747144B1 (en) | 1998-08-27 | 2004-06-08 | Spirogen Limited | Collections of compounds |
| US7049311B1 (en) | 1998-08-27 | 2006-05-23 | Spirogen Limited | Pyrrolbenzodiazepines |
| US7067511B2 (en) | 1998-08-27 | 2006-06-27 | Spirogen Limited | Pyrrolobenzodiazepines |
| US7265105B2 (en) | 1998-08-27 | 2007-09-04 | Spirogen Limited | Pyrrolobenzodiazepines |
| JP4824165B2 (ja) * | 1998-08-27 | 2011-11-30 | スパイロジエン・リミテツド | ピロロベンゾジアゼピン類 |
| US6909006B1 (en) | 1999-08-27 | 2005-06-21 | Spirogen Limited | Cyclopropylindole derivatives |
| US7407951B2 (en) | 2002-11-14 | 2008-08-05 | Spirogen Limited | Pyrrolobenzodiazepines |
| US7429658B2 (en) | 2003-09-11 | 2008-09-30 | Spirogen Limited | Synthesis of protected pyrrolobenzodiazepines |
| US7557099B2 (en) | 2004-03-01 | 2009-07-07 | Spirogen Limited | Pyrrolobenzodiazepines as key intermediates in the synthesis of dimeric cytotoxic pyrrolobenzodiazepines |
| US7741319B2 (en) | 2004-03-01 | 2010-06-22 | 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 |
| US7528126B2 (en) | 2004-03-09 | 2009-05-05 | Spirogen Limited | Pyrrolobenzodiazepines |
| US8592576B2 (en) | 2008-10-17 | 2013-11-26 | Spirogen Sarl | Unsymmetrical pyrrolobenzodiazepine-dimers for treatment of proliferative diseases |
| US9624227B2 (en) | 2008-10-17 | 2017-04-18 | Medimmune Limited | Unsymmetrical pyrrolobenzodiazepine-dimers for treatment of proliferative diseases |
| US8940733B2 (en) | 2008-10-17 | 2015-01-27 | Spirogen Sarl | Unsymmetrical pyrrolobenzodiazepine-dimers for treatment of proliferative diseases |
| US8697688B2 (en) | 2010-04-15 | 2014-04-15 | Seattle Genetics Inc. | Pyrrolobenzodiazepines used to treat proliferative diseases |
| US8829184B2 (en) | 2010-04-15 | 2014-09-09 | Spirogen Sarl | Intermediates useful for the synthesis of pyrrolobenzodiazepines |
| US10561739B2 (en) | 2010-04-15 | 2020-02-18 | Seattle Genetics Inc. | Targeted pyrrolobenzodiazapine conjugates |
| US9242013B2 (en) | 2010-04-15 | 2016-01-26 | Seattle Genetics Inc. | Targeted pyrrolobenzodiazapine conjugates |
| US9732084B2 (en) | 2010-04-15 | 2017-08-15 | Medimmune Limited | Pyrrolobenzodiazepines used to treat proliferative diseases |
| US9592240B2 (en) | 2010-04-15 | 2017-03-14 | Seattle Genetics Inc. | Targeted pyrrolobenzodiazapine conjugates |
| US9399641B2 (en) | 2011-09-20 | 2016-07-26 | Medimmune Limited | Pyrrolobenzodiazepines as unsymmetrical dimeric PBD compounds for inclusion in targeted conjugates |
| US9526798B2 (en) | 2011-10-14 | 2016-12-27 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines and targeted conjugates |
| US9399073B2 (en) | 2011-10-14 | 2016-07-26 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines |
| US20140286970A1 (en) | 2011-10-14 | 2014-09-25 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines and targeted conjugates |
| US9388187B2 (en) | 2011-10-14 | 2016-07-12 | Medimmune Limited | Pyrrolobenzodiazepines |
| US10329352B2 (en) | 2011-10-14 | 2019-06-25 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines and targeted conjugates |
| US9707301B2 (en) | 2011-10-14 | 2017-07-18 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines and targeted conjugates |
| US9713647B2 (en) | 2011-10-14 | 2017-07-25 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines and targeted conjugates |
| US9387259B2 (en) | 2011-10-14 | 2016-07-12 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines and targeted conjugates |
| US9102704B2 (en) | 2011-10-14 | 2015-08-11 | Spirogen Sarl | Synthesis method and intermediates useful in the preparation of pyrrolobenzodiazepines |
| US10328084B2 (en) | 2011-10-14 | 2019-06-25 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines and targeted conjugates |
| US10994023B2 (en) | 2012-10-12 | 2021-05-04 | Medimmune Limited | Pyrrolobenzodiazepines and conjugates thereof |
| US11779650B2 (en) | 2012-10-12 | 2023-10-10 | Medimmune Limited | Pyrrolobenzodiazepine-antibody conjugates |
| US11690918B2 (en) | 2012-10-12 | 2023-07-04 | Medimmune Limited | Pyrrolobenzodiazepine-anti-CD22 antibody conjugates |
| US11701430B2 (en) | 2012-10-12 | 2023-07-18 | Medimmune Limited | Pyrrolobenzodiazepines and conjugates thereof |
| US11771775B2 (en) | 2012-10-12 | 2023-10-03 | Medimmune Limited | Pyrrolobenzodiazepine-antibody conjugates |
| US9415117B2 (en) | 2012-10-12 | 2016-08-16 | Medimmune Limited | Pyrrolobenzodiazepines and conjugates thereof |
| US9931415B2 (en) | 2012-10-12 | 2018-04-03 | Medimmune Limited | Pyrrolobenzodiazepine-antibody conjugates |
| US9919056B2 (en) | 2012-10-12 | 2018-03-20 | Adc Therapeutics S.A. | Pyrrolobenzodiazepine-anti-CD22 antibody conjugates |
| US10335497B2 (en) | 2012-10-12 | 2019-07-02 | Medimmune Limited | Pyrrolobenzodiazepines and conjugates thereof |
| US10799596B2 (en) | 2012-10-12 | 2020-10-13 | Adc Therapeutics S.A. | Pyrrolobenzodiazepine-antibody conjugates |
| US10780181B2 (en) | 2012-10-12 | 2020-09-22 | Medimmune Limited | Pyrrolobenzodiazepine-antibody conjugates |
| US9931414B2 (en) | 2012-10-12 | 2018-04-03 | Medimmune Limited | Pyrrolobenzodiazepine-antibody conjugates |
| US12121590B2 (en) | 2012-10-12 | 2024-10-22 | Medimmune Limited | Pyrrolobenzodiazepines and conjugates thereof |
| US9745303B2 (en) | 2012-10-12 | 2017-08-29 | Medimmune Limited | Synthesis and intermediates of pyrrolobenzodiazepine derivatives for conjugation |
| US10646584B2 (en) | 2012-10-12 | 2020-05-12 | Medimmune Limited | Pyrrolobenzodiazepines and conjugates thereof |
| US10751346B2 (en) | 2012-10-12 | 2020-08-25 | Medimmune Limited | Pyrrolobenzodiazepine—anti-PSMA antibody conjugates |
| US10695433B2 (en) | 2012-10-12 | 2020-06-30 | Medimmune Limited | Pyrrolobenzodiazepine-antibody conjugates |
| US10722594B2 (en) | 2012-10-12 | 2020-07-28 | Adc Therapeutics S.A. | Pyrrolobenzodiazepine-anti-CD22 antibody conjugates |
| US10736903B2 (en) | 2012-10-12 | 2020-08-11 | Medimmune Limited | Pyrrolobenzodiazepine-anti-PSMA antibody conjugates |
| US10010624B2 (en) | 2013-10-11 | 2018-07-03 | Medimmune Limited | Pyrrolobenzodiazepine-antibody conjugates |
| US9956298B2 (en) | 2013-10-11 | 2018-05-01 | Medimmune Limited | Pyrrolobenzodiazepines and conjugates thereof |
| US9956299B2 (en) | 2013-10-11 | 2018-05-01 | Medimmune Limited | Pyrrolobenzodiazepine—antibody conjugates |
| US9950078B2 (en) | 2013-10-11 | 2018-04-24 | Medimmune Limited | Pyrrolobenzodiazepine-antibody conjugates |
| US10420777B2 (en) | 2014-09-12 | 2019-09-24 | Medimmune Limited | Pyrrolobenzodiazepines and conjugates thereof |
| US10780096B2 (en) | 2014-11-25 | 2020-09-22 | Adc Therapeutics Sa | Pyrrolobenzodiazepine-antibody conjugates |
| US11059893B2 (en) | 2015-04-15 | 2021-07-13 | Bergenbio Asa | Humanized anti-AXL antibodies |
| US11702473B2 (en) | 2015-04-15 | 2023-07-18 | Medimmune Limited | Site-specific antibody-drug conjugates |
| US10392393B2 (en) | 2016-01-26 | 2019-08-27 | Medimmune Limited | Pyrrolobenzodiazepines |
| US10695439B2 (en) | 2016-02-10 | 2020-06-30 | Medimmune Limited | Pyrrolobenzodiazepine conjugates |
| US11517626B2 (en) | 2016-02-10 | 2022-12-06 | Medimmune Limited | Pyrrolobenzodiazepine antibody conjugates |
| US10543279B2 (en) | 2016-04-29 | 2020-01-28 | Medimmune Limited | Pyrrolobenzodiazepine conjugates and their use for the treatment of cancer |
| US10799595B2 (en) | 2016-10-14 | 2020-10-13 | Medimmune Limited | Pyrrolobenzodiazepine conjugates |
| US11612665B2 (en) | 2017-02-08 | 2023-03-28 | Medimmune Limited | Pyrrolobenzodiazepine-antibody conjugates |
| US11160872B2 (en) | 2017-02-08 | 2021-11-02 | Adc Therapeutics Sa | Pyrrolobenzodiazepine-antibody conjugates |
| US11813335B2 (en) | 2017-02-08 | 2023-11-14 | Medimmune Limited | Pyrrolobenzodiazepine-antibody conjugates |
| US11370801B2 (en) | 2017-04-18 | 2022-06-28 | Medimmune Limited | Pyrrolobenzodiazepine conjugates |
| US10544223B2 (en) | 2017-04-20 | 2020-01-28 | Adc Therapeutics Sa | Combination therapy with an anti-axl antibody-drug conjugate |
| US11318211B2 (en) | 2017-06-14 | 2022-05-03 | Adc Therapeutics Sa | Dosage regimes for the administration of an anti-CD19 ADC |
| US11938192B2 (en) | 2017-06-14 | 2024-03-26 | Medimmune Limited | Dosage regimes for the administration of an anti-CD19 ADC |
| US11649250B2 (en) | 2017-08-18 | 2023-05-16 | Medimmune Limited | Pyrrolobenzodiazepine conjugates |
| US11352324B2 (en) | 2018-03-01 | 2022-06-07 | Medimmune Limited | Methods |
| US11524969B2 (en) | 2018-04-12 | 2022-12-13 | Medimmune Limited | Pyrrolobenzodiazepines and conjugates thereof as antitumour agents |
| US12209099B2 (en) | 2019-03-15 | 2025-01-28 | Medimmune Limited | Azetidobenzodiazepine dimers and conjugates comprising them for use in the treatment of cancer |
Also Published As
| Publication number | Publication date |
|---|---|
| IL33558A0 (en) | 1970-04-20 |
| FI46259C (fi) | 1973-02-12 |
| IL33558A (en) | 1973-10-25 |
| ES375013A1 (es) | 1972-03-01 |
| IE33906L (en) | 1970-06-30 |
| RO55813A (enrdf_load_stackoverflow) | 1974-02-01 |
| IE33906B1 (en) | 1974-12-11 |
| FI46259B (enrdf_load_stackoverflow) | 1972-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |