LU82272A1 - Nouveau compose du benzodiazepine - Google Patents
Nouveau compose du benzodiazepine Download PDFInfo
- Publication number
- LU82272A1 LU82272A1 LU82272A LU82272A LU82272A1 LU 82272 A1 LU82272 A1 LU 82272A1 LU 82272 A LU82272 A LU 82272A LU 82272 A LU82272 A LU 82272A LU 82272 A1 LU82272 A1 LU 82272A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- compound
- formula
- acid
- hydrogen atom
- acrylamide
- Prior art date
Links
- -1 BENZODIAZEPINE COMPOUND Chemical class 0.000 title claims description 20
- 229940049706 benzodiazepine Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 43
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 239000003513 alkali Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 125000002252 acyl group Chemical group 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 7
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 150000003464 sulfur compounds Chemical class 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims description 3
- KRURGYOKPVLRHQ-UHFFFAOYSA-N trithionic acid Chemical compound OS(=O)(=O)SS(O)(=O)=O KRURGYOKPVLRHQ-UHFFFAOYSA-N 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 229910001882 dioxygen Inorganic materials 0.000 claims description 2
- RMGVZKRVHHSUIM-UHFFFAOYSA-N dithionic acid Chemical compound OS(=O)(=O)S(O)(=O)=O RMGVZKRVHHSUIM-UHFFFAOYSA-N 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 239000003760 tallow Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 claims 3
- 229910006080 SO2X Inorganic materials 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 101000650578 Salmonella phage P22 Regulatory protein C3 Proteins 0.000 claims 1
- 101001040920 Triticum aestivum Alpha-amylase inhibitor 0.28 Proteins 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- WBZKQQHYRPRKNJ-UHFFFAOYSA-N disulfurous acid Chemical compound OS(=O)S(O)(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-N 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- BIVATAPISXAMKP-UHFFFAOYSA-N 3-(1h-1,4-benzodiazepin-2-yl)prop-2-enamide Chemical compound N1C(C=CC(=O)N)=CN=CC2=CC=CC=C21 BIVATAPISXAMKP-UHFFFAOYSA-N 0.000 description 23
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 18
- 239000013078 crystal Substances 0.000 description 13
- 238000000862 absorption spectrum Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 239000011734 sodium Substances 0.000 description 10
- 230000000259 anti-tumor effect Effects 0.000 description 9
- 159000000000 sodium salts Chemical class 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 230000004083 survival effect Effects 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229920001429 chelating resin Polymers 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- CSMWJXBSXGUPGY-UHFFFAOYSA-L sodium dithionate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)S([O-])(=O)=O CSMWJXBSXGUPGY-UHFFFAOYSA-L 0.000 description 2
- 229940075931 sodium dithionate Drugs 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 231100000820 toxicity test Toxicity 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- HGOZVUMJMGXJJB-UHFFFAOYSA-N 3-(7h-pyrrolo[2,1-c][1,4]benzodiazepin-8-yl)prop-2-enamide Chemical compound C1=C2C=CC=CC2=NC=C2CC(C=CC(=O)N)=CN21 HGOZVUMJMGXJJB-UHFFFAOYSA-N 0.000 description 1
- MRGGOAHOCOOIMN-UHFFFAOYSA-N 3-(9H-pyrrolo[2,1-c][1,4]benzodiazepin-8-yl)prop-2-enamide Chemical compound C1=C(CN2C1=CN=C1C(=C2)C=CC=C1)C=CC(=O)N MRGGOAHOCOOIMN-UHFFFAOYSA-N 0.000 description 1
- OBAIHJABYRUGAP-UHFFFAOYSA-N 3-(diazepin-1-yl)prop-2-enamide Chemical compound NC(=O)C=CN1C=CC=CC=N1 OBAIHJABYRUGAP-UHFFFAOYSA-N 0.000 description 1
- UQQCSQDEJSQBEE-UHFFFAOYSA-N 5-acetyl-4-acetyloxy-8-(3-amino-3-oxoprop-1-enyl)-3-methyl-11-oxo-6a,7-dihydro-6h-pyrrolo[2,1-c][1,4]benzodiazepine-6-sulfonic acid Chemical compound CC(=O)N1C(S(O)(=O)=O)C2CC(C=CC(N)=O)=CN2C(=O)C2=C1C(OC(=O)C)=C(C)C=C2 UQQCSQDEJSQBEE-UHFFFAOYSA-N 0.000 description 1
- MTAYQCUQVQQGHP-UHFFFAOYSA-N 8-(3-amino-3-oxoprop-1-enyl)-4-methoxycarbonyloxy-3-methyl-11-oxo-5,6,6a,7-tetrahydropyrrolo[2,1-c][1,4]benzodiazepine-6-sulfonic acid Chemical compound N1C(S(O)(=O)=O)C2CC(C=CC(N)=O)=CN2C(=O)C2=C1C(OC(=O)OC)=C(C)C=C2 MTAYQCUQVQQGHP-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- 101100328518 Caenorhabditis elegans cnt-1 gene Proteins 0.000 description 1
- 206010048610 Cardiotoxicity Diseases 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 229920006063 Lamide® Polymers 0.000 description 1
- 208000008342 Leukemia P388 Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- JLNTWVDSQRNWFU-UHFFFAOYSA-N OOOOOOO Chemical compound OOOOOOO JLNTWVDSQRNWFU-UHFFFAOYSA-N 0.000 description 1
- UIQWBVPFHHQZHH-UHFFFAOYSA-N OOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOO UIQWBVPFHHQZHH-UHFFFAOYSA-N 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- 101150052863 THY1 gene Proteins 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- WVHBHPATSLQXGC-UHFFFAOYSA-N benzene;ethanol Chemical compound CCO.C1=CC=CC=C1 WVHBHPATSLQXGC-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 231100000259 cardiotoxicity Toxicity 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000213 sulfino group Chemical group [H]OS(*)=O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 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
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8988679 | 1979-07-17 | ||
| JP8988679A JPS5615289A (en) | 1979-07-17 | 1979-07-17 | Novel benzodiazepinnbased compound 3 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU82272A1 true LU82272A1 (fr) | 1980-07-01 |
Family
ID=13983232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU82272A LU82272A1 (fr) | 1979-07-17 | 1980-03-19 | Nouveau compose du benzodiazepine |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4309437A (enExample) |
| JP (1) | JPS5615289A (enExample) |
| BE (1) | BE882305A (enExample) |
| CA (1) | CA1152985A (enExample) |
| CH (1) | CH648848A5 (enExample) |
| DE (1) | DE3010544C2 (enExample) |
| FR (1) | FR2461711A1 (enExample) |
| GB (1) | GB2053894B (enExample) |
| LU (1) | LU82272A1 (enExample) |
| NL (1) | NL8001531A (enExample) |
| SE (1) | SE436882B (enExample) |
Families Citing this family (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1214774A (en) * | 1983-02-10 | 1986-12-02 | Yusei Shiraga | Benzodiazepine derivative |
| JPS59152329A (ja) * | 1983-02-17 | 1984-08-31 | Green Cross Corp:The | 局所障害抑制剤 |
| JPS60168512U (ja) * | 1985-03-25 | 1985-11-08 | 株式会社栗田機械製作所 | 圧搾濾板の圧搾膜検査装置 |
| ATE320436T1 (de) * | 1998-08-27 | 2006-04-15 | Spirogen Ltd | Dimere pyrrolobenzodiazepine |
| GB9818730D0 (en) * | 1998-08-27 | 1998-10-21 | Univ Portsmouth | Collections of compounds |
| GB9818731D0 (en) * | 1998-08-27 | 1998-10-21 | Univ Portsmouth | Compounds |
| 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 |
| 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 |
| PT2270010E (pt) * | 2004-03-01 | 2012-03-12 | Spirogen Ltd | Derivados de 11-hidroxi-5h-pirrolo[2,1-c][1,4]benzodiazepin- 5-ona como intermediários chave para a preparação de pirrolobenzodiazepinas substituídas em c2 |
| WO2005085260A1 (en) * | 2004-03-09 | 2005-09-15 | Spirogen Limited | Pyrrolobenzodiazepines |
| PT1879901E (pt) * | 2005-04-21 | 2010-03-29 | Spirogen Ltd | Pirrolobenzodiazepinas |
| 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 |
| ES2623057T3 (es) | 2010-04-15 | 2017-07-10 | Medimmune Limited | 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 |
| 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 |
| AU2012322933B2 (en) | 2011-10-14 | 2017-02-02 | Medimmune Limited | Synthesis method and intermediates useful in the preparation of pyrrolobenzodiazepines |
| CA2850375C (en) | 2011-10-14 | 2019-07-02 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines and targeted conjugates |
| CN103998449A (zh) | 2011-10-14 | 2014-08-20 | 斯皮罗根有限公司 | 吡咯并苯并二氮杂卓 |
| CN103998450B (zh) | 2011-10-14 | 2017-03-08 | 麦迪穆有限责任公司 | 吡咯并苯并二氮杂卓 |
| CA2850373C (en) | 2011-10-14 | 2019-07-16 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines and targeted conjugates |
| NZ701478A (en) | 2012-04-30 | 2016-08-26 | Medimmune Ltd | Pyrrolobenzodiazepines |
| WO2014057120A1 (en) | 2012-10-12 | 2014-04-17 | Adc Therapeutics Sàrl | Pyrrolobenzodiazepine-antibody conjugates |
| HRP20180945T1 (hr) | 2012-10-12 | 2018-08-10 | Adc Therapeutics Sa | Konjugati protutijelo-pirolobenzodiazepin |
| CA2885305C (en) | 2012-10-12 | 2019-11-12 | Spirogen Sarl | Synthesis and intermediates of pyrrolobenzodiazepine derivatives for conjugation |
| LT2906251T (lt) | 2012-10-12 | 2017-12-11 | Adc Therapeutics Sa | Pirolobenzodiazepino-anti-cd22 antikūno konjugatai |
| PT2906253T (pt) | 2012-10-12 | 2018-11-05 | Medimmune Ltd | Conjugados de anticorpo anti-psma de pirrolobenzodiazepina |
| ES2680153T3 (es) | 2012-10-12 | 2018-09-04 | Adc Therapeutics Sa | Conjugados de anticuerpos anti-PSMA-pirrolobenzodiazepinas |
| RS58921B1 (sr) | 2012-10-12 | 2019-08-30 | Medimmune Ltd | Pirolobenzodiazepini i njihovi konjugati |
| CN104703630A (zh) | 2012-10-12 | 2015-06-10 | 斯皮罗根有限公司 | 吡咯并苯并二氮杂卓及其结合物 |
| HRP20182129T1 (hr) | 2012-10-12 | 2019-02-08 | Adc Therapeutics Sa | Konjugati protutijelo - pirolobenzodiazepin |
| WO2015052532A1 (en) | 2013-10-11 | 2015-04-16 | Spirogen Sàrl | Pyrrolobenzodiazepine-antibody conjugates |
| 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 |
| 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 |
| KR20170101895A (ko) | 2014-11-25 | 2017-09-06 | 에이디씨 테라퓨틱스 에스에이 | 피롤로벤조디아제핀-항체 접합체 |
| 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 |
| 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 |
| GB201607478D0 (en) | 2016-04-29 | 2016-06-15 | Medimmune Ltd | Pyrrolobenzodiazepine Conjugates |
| WO2017201132A2 (en) | 2016-05-18 | 2017-11-23 | Mersana Therapeutics, Inc. | Pyrrolobenzodiazepines and conjugates thereof |
| JP7049276B2 (ja) | 2016-06-24 | 2022-04-06 | メルサナ セラピューティクス インコーポレイテッド | ピロロベンゾジアゼピンおよびその結合体 |
| GB201617466D0 (en) | 2016-10-14 | 2016-11-30 | Medimmune Ltd | Pyrrolobenzodiazepine conjugates |
| SI3544636T1 (sl) | 2017-02-08 | 2021-08-31 | Adc Therapeutics Sa | Konjugati pirolobenzodiazepin-protitelo |
| GB201702031D0 (en) | 2017-02-08 | 2017-03-22 | Medlmmune Ltd | Pyrrolobenzodiazepine-antibody conjugates |
| HRP20221063T1 (hr) | 2017-04-18 | 2022-11-11 | Medimmune Limited | Konjugati pirolobenzodiazepina |
| WO2018193102A1 (en) | 2017-04-20 | 2018-10-25 | Adc Therapeutics Sa | Combination therapy with an anti-axl antibody-drug conjugate |
| ES2988683T3 (es) | 2017-06-14 | 2024-11-21 | Adc Therapeutics Sa | Pautas posológicas para la administración de un CAF anti-CD19 |
| JP7220203B2 (ja) | 2017-08-18 | 2023-02-09 | メドイミューン・リミテッド | ピロロベンゾジアゼピン複合体 |
| 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 |
| 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 |
| USD925487S1 (en) * | 2019-10-22 | 2021-07-20 | Lg Electronics Inc. | Audio player |
Family Cites Families (2)
| 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 |
-
1979
- 1979-07-17 JP JP8988679A patent/JPS5615289A/ja active Granted
-
1980
- 1980-02-25 SE SE8001458A patent/SE436882B/sv not_active IP Right Cessation
- 1980-02-27 CA CA000346511A patent/CA1152985A/en not_active Expired
- 1980-03-04 US US06/127,984 patent/US4309437A/en not_active Expired - Lifetime
- 1980-03-10 GB GB8008033A patent/GB2053894B/en not_active Expired
- 1980-03-14 NL NL8001531A patent/NL8001531A/nl not_active Application Discontinuation
- 1980-03-19 LU LU82272A patent/LU82272A1/fr unknown
- 1980-03-19 DE DE3010544A patent/DE3010544C2/de not_active Expired
- 1980-03-19 FR FR8006153A patent/FR2461711A1/fr active Granted
- 1980-03-19 BE BE0/199851A patent/BE882305A/fr not_active IP Right Cessation
- 1980-03-20 CH CH2187/80A patent/CH648848A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2461711A1 (fr) | 1981-02-06 |
| US4309437A (en) | 1982-01-05 |
| JPS5615289A (en) | 1981-02-14 |
| JPS6237631B2 (enExample) | 1987-08-13 |
| FR2461711B1 (enExample) | 1983-05-13 |
| DE3010544A1 (de) | 1981-01-29 |
| CA1152985A (en) | 1983-08-30 |
| GB2053894B (en) | 1983-04-20 |
| CH648848A5 (de) | 1985-04-15 |
| GB2053894A (en) | 1981-02-11 |
| DE3010544C2 (de) | 1982-07-01 |
| SE436882B (sv) | 1985-01-28 |
| BE882305A (fr) | 1980-07-16 |
| NL8001531A (nl) | 1981-01-20 |
| SE8001458L (sv) | 1981-01-18 |
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