CA2871172C - Pyrrolobenzodiazepines - Google Patents
Pyrrolobenzodiazepines Download PDFInfo
- Publication number
- CA2871172C CA2871172C CA2871172A CA2871172A CA2871172C CA 2871172 C CA2871172 C CA 2871172C CA 2871172 A CA2871172 A CA 2871172A CA 2871172 A CA2871172 A CA 2871172A CA 2871172 C CA2871172 C CA 2871172C
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- Canada
- Prior art keywords
- compound according
- group
- methyl
- alkyl
- nme
- Prior art date
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- YUOCYTRGANSSRY-UHFFFAOYSA-N pyrrolo[2,3-i][1,2]benzodiazepine Chemical class C1=CN=NC2=C3C=CN=C3C=CC2=C1 YUOCYTRGANSSRY-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 122
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 15
- 201000010099 disease Diseases 0.000 claims abstract description 14
- 239000012453 solvate Substances 0.000 claims abstract description 12
- 230000002062 proliferating effect Effects 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 102
- -1 methoxy, ethoxy Chemical group 0.000 claims description 92
- 125000003118 aryl group Chemical group 0.000 claims description 65
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 61
- 125000000623 heterocyclic group Chemical group 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 39
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000004970 halomethyl group Chemical group 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000005488 carboaryl group Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000006593 (C2-C3) alkynyl group Chemical group 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims description 2
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000004551 isoquinolin-3-yl group Chemical group C1=NC(=CC2=CC=CC=C12)* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- 238000006243 chemical reaction Methods 0.000 description 39
- 239000000243 solution Substances 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- 229910001868 water Inorganic materials 0.000 description 31
- 238000003756 stirring Methods 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 26
- 238000004809 thin layer chromatography Methods 0.000 description 26
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 24
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 20
- 239000007787 solid Substances 0.000 description 19
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 18
- 125000003277 amino group Chemical group 0.000 description 17
- 125000006413 ring segment Chemical group 0.000 description 17
- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
- 206010028980 Neoplasm Diseases 0.000 description 16
- 229910052739 hydrogen Inorganic materials 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- 230000000694 effects Effects 0.000 description 15
- 230000002829 reductive effect Effects 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- 238000010511 deprotection reaction Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 13
- 239000012267 brine Substances 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 12
- 239000003242 anti bacterial agent Substances 0.000 description 12
- 229940088710 antibiotic agent Drugs 0.000 description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
- 229920006395 saturated elastomer Polymers 0.000 description 12
- 238000003556 assay Methods 0.000 description 11
- 239000012043 crude product Substances 0.000 description 10
- 238000003818 flash chromatography Methods 0.000 description 10
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 9
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- QWHNJUXXYKPLQM-UHFFFAOYSA-N dimethyl cyclopentane Natural products CC1(C)CCCC1 QWHNJUXXYKPLQM-UHFFFAOYSA-N 0.000 description 9
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 238000001727 in vivo Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 7
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- YMXFJTUQQVLJEN-UHFFFAOYSA-N pyrimidine Chemical compound C1=CN=CN=C1.C1=CN=CN=C1 YMXFJTUQQVLJEN-UHFFFAOYSA-N 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 238000002560 therapeutic procedure Methods 0.000 description 7
- 206010006187 Breast cancer Diseases 0.000 description 6
- 208000026310 Breast neoplasm Diseases 0.000 description 6
- 101150041968 CDC13 gene Proteins 0.000 description 6
- 230000004568 DNA-binding Effects 0.000 description 6
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 6
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000000562 conjugate Substances 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 6
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
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- 239000012265 solid product Substances 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 description 5
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Classifications
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- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
- A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
- A61K31/5517—1,4-Benzodiazepines, e.g. diazepam or clozapine condensed with five-membered rings having nitrogen as a ring hetero atom, e.g. imidazobenzodiazepines, triazolam
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
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|---|---|---|---|
| US201261640310P | 2012-04-30 | 2012-04-30 | |
| US61/640,310 | 2012-04-30 | ||
| PCT/GB2013/051098 WO2013164593A1 (en) | 2012-04-30 | 2013-04-30 | Pyrrolobenzodiazepines |
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| CA2871172A1 CA2871172A1 (en) | 2013-11-07 |
| CA2871172C true CA2871172C (en) | 2020-08-25 |
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| CA2871172A Expired - Fee Related CA2871172C (en) | 2012-04-30 | 2013-04-30 | Pyrrolobenzodiazepines |
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|---|---|
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| EP (1) | EP2855482B1 (enExample) |
| JP (1) | JP6157596B2 (enExample) |
| KR (1) | KR101960129B1 (enExample) |
| CN (1) | CN104684914B (enExample) |
| AU (1) | AU2013255613B2 (enExample) |
| BR (1) | BR112014027143B1 (enExample) |
| CA (1) | CA2871172C (enExample) |
| ES (1) | ES2623042T3 (enExample) |
| IN (1) | IN2014MN02092A (enExample) |
| MX (1) | MX369715B (enExample) |
| NZ (1) | NZ701290A (enExample) |
| WO (1) | WO2013164593A1 (enExample) |
| ZA (1) | ZA201407759B (enExample) |
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| 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 |
| CA2850103C (en) | 2011-10-14 | 2019-09-10 | Spirogen Sarl | Pyrrolobenzodiazepines |
| 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 |
| 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 |
| EP2830126B1 (en) * | 2013-05-07 | 2019-07-03 | LG Chem, Ltd. | Electrode for secondary battery, preparation thereof, and secondary battery and cable-type secondary battery comprising the same |
| GB201317982D0 (en) | 2013-10-11 | 2013-11-27 | Spirogen Sarl | Pyrrolobenzodiazepines and conjugates thereof |
| GB201317981D0 (en) | 2013-10-11 | 2013-11-27 | Spirogen Sarl | Pyrrolobenzodiazepines and conjugates thereof |
| GB201407816D0 (en) | 2014-05-02 | 2014-06-18 | King S College London | Pyrrolobenzodiazepine Compounds |
| 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 |
| 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 |
| GB201510010D0 (en) | 2015-06-09 | 2015-07-22 | King S College London | PDD and BPD compounds |
| GB201514928D0 (en) | 2015-08-21 | 2015-10-07 | King S College London | PDD compounds |
| US20180339985A1 (en) | 2015-08-21 | 2018-11-29 | Femtogenix Limited | Pdd compounds |
| 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 |
| EP3604311A4 (en) | 2017-03-29 | 2021-01-13 | LegoChem Biosciences, Inc. | PYRROLOBENZODIAZEPINE DIMERIC PRECURSOR AND ASSOCIATED LIGAND-BOND CONJUGATE COMPOUND |
| 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 |
| EP3727463A1 (en) | 2017-12-21 | 2020-10-28 | Mersana Therapeutics, Inc. | Pyrrolobenzodiazepine antibody conjugates |
| GB201803342D0 (en) | 2018-03-01 | 2018-04-18 | Medimmune Ltd | Methods |
| SG11202009308WA (en) | 2018-03-28 | 2020-10-29 | Mitsubishi Tanabe Pharma Corp | DRUG CONJUGATES OF cMET MONOCLONAL BINDING AGENTS, AND USES THEREOF |
| GB201806022D0 (en) | 2018-04-12 | 2018-05-30 | Medimmune Ltd | Pyrrolobenzodiazepines and conjugates thereof |
| KR20200084802A (ko) | 2019-01-03 | 2020-07-13 | 주식회사 레고켐 바이오사이언스 | 안전성이 향상된 피롤로벤조디아제핀 이량체 화합물 및 이의 용도 |
| WO2020141923A2 (ko) | 2019-01-03 | 2020-07-09 | 주식회사 레고켐 바이오사이언스 | 안전성이 향상된 피롤로벤조디아제핀 이량체 화합물 및 이의 용도 |
| GB201901197D0 (en) | 2019-01-29 | 2019-03-20 | Femtogenix Ltd | G-A Crosslinking cytotoxic agents |
| IL286326B2 (en) | 2019-03-15 | 2025-10-01 | Medimmune Ltd | Azatidobenzodiazepine dimers and conjugates containing them for use in the treatment of cancer |
| 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 |
| GB202405758D0 (en) | 2024-04-24 | 2024-06-05 | King S College London | Compounds |
Family Cites Families (27)
| 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 |
| 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 |
| 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 |
| US6187797B1 (en) | 1996-12-23 | 2001-02-13 | Dupont Pharmaceuticals Company | Phenyl-isoxazoles as factor XA Inhibitors |
| WO1999046244A1 (en) | 1998-03-12 | 1999-09-16 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (ptpases) |
| GB9818730D0 (en) | 1998-08-27 | 1998-10-21 | Univ Portsmouth | Collections of compounds |
| GB9818731D0 (en) | 1998-08-27 | 1998-10-21 | Univ Portsmouth | Compounds |
| DK1193270T3 (da) | 1998-08-27 | 2003-09-15 | Spirogen Ltd | Pyrrolobenzodiazepiner |
| GB9818732D0 (en) | 1998-08-27 | 1998-10-21 | Univ Portsmouth | Collection 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. |
| 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 |
| GB0404577D0 (en) | 2004-03-01 | 2004-04-07 | Spirogen Ltd | Pyrrolobenzodiazepines |
| GB0404578D0 (en) | 2004-03-01 | 2004-04-07 | Spirogen Ltd | Pyrrolobenzodiazepines |
| GB0404574D0 (en) | 2004-03-01 | 2004-04-07 | Spirogen Ltd | Amino acids |
| 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 |
| ATE427949T1 (de) * | 2005-10-05 | 2009-04-15 | Spirogen Ltd | 4-a4-(5-oxo-2,3,5,11a-tetrahydro-5h-pyrrolo a2, 1-cua1,4ubenzodiazepin-8-yloxy)-butyrylaminou-1 - pyrrol-2-carbonsaurealkylesterderivate und verwandte verbindung zur behandlung einer proliferativen erkrankung |
| DE102007029116A1 (de) * | 2007-06-25 | 2009-01-02 | Continental Automotive Gmbh | Verfahren zum Betreiben eines Mikrocontrollers und einer Ausführungseinheit sowie ein Mikrocontroller und eine Ausführungseinheit |
| GB0722088D0 (en) * | 2007-11-09 | 2007-12-19 | Spirogen Ltd | Pyrrolobenzodiazepines |
| GB0813432D0 (en) | 2008-07-22 | 2008-08-27 | Spirogen Ltd | Pyrrolobenzodiazepines |
| GB0819095D0 (en) | 2008-10-17 | 2008-11-26 | Spirogen Ltd | Pyrrolobenzodiazepines |
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| EP2855482A1 (en) | 2015-04-08 |
| HK1208444A1 (en) | 2016-03-04 |
| WO2013164593A1 (en) | 2013-11-07 |
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| JP6157596B2 (ja) | 2017-07-05 |
| NZ701290A (en) | 2016-08-26 |
| US20150133435A1 (en) | 2015-05-14 |
| KR101960129B1 (ko) | 2019-03-19 |
| MX369715B (es) | 2019-11-20 |
| BR112014027143B1 (pt) | 2020-06-09 |
| EP2855482B1 (en) | 2017-03-01 |
| ES2623042T3 (es) | 2017-07-10 |
| JP2015515972A (ja) | 2015-06-04 |
| ZA201407759B (en) | 2015-11-25 |
| MX2014013098A (es) | 2015-04-14 |
| US9376440B2 (en) | 2016-06-28 |
| CN104684914A (zh) | 2015-06-03 |
| KR20150016245A (ko) | 2015-02-11 |
| CN104684914B (zh) | 2017-12-15 |
| AU2013255613A1 (en) | 2014-11-13 |
| IN2014MN02092A (enExample) | 2015-09-04 |
| CA2871172A1 (en) | 2013-11-07 |
| BR112014027143A2 (pt) | 2017-06-27 |
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