DK168073B1 - Analogifremgangsmaade til fremstilling af imidazodiazepiner eller farmaceutisk acceptable syreadditionssalte deraf - Google Patents
Analogifremgangsmaade til fremstilling af imidazodiazepiner eller farmaceutisk acceptable syreadditionssalte deraf Download PDFInfo
- Publication number
- DK168073B1 DK168073B1 DK074282A DK74282A DK168073B1 DK 168073 B1 DK168073 B1 DK 168073B1 DK 074282 A DK074282 A DK 074282A DK 74282 A DK74282 A DK 74282A DK 168073 B1 DK168073 B1 DK 168073B1
- Authority
- DK
- Denmark
- Prior art keywords
- tert
- halogen
- group
- butyl
- hydrogen
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 85
- 238000000034 method Methods 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 42
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- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 36
- 150000002367 halogens Chemical class 0.000 claims description 36
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 34
- 150000002431 hydrogen Chemical class 0.000 claims description 32
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 31
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- 125000004414 alkyl thio group Chemical group 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
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- 125000003277 amino group Chemical group 0.000 claims description 14
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- 125000003545 alkoxy group Chemical group 0.000 claims description 6
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 210000003800 pharynx Anatomy 0.000 description 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- XRKUMJSBSIOYDE-AWEZNQCLSA-N t-butyl (s)-7-amino-11,12,13,13a-tetrahydro-9-oxo-9h-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate Chemical compound O=C1C2=CC(N)=CC=C2N2C=NC(C(=O)OC(C)(C)C)=C2[C@@H]2CCCN21 XRKUMJSBSIOYDE-AWEZNQCLSA-N 0.000 description 1
- ALIPPSZCAOOVCT-LBPRGKRZSA-N t-butyl (s)-7-amino-8-bromo-11,12,13,13a-tetrahydro-9-oxo-9h-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate Chemical compound O=C1C2=C(Br)C(N)=CC=C2N2C=NC(C(=O)OC(C)(C)C)=C2[C@@H]2CCCN21 ALIPPSZCAOOVCT-LBPRGKRZSA-N 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- WNNMAVYBIDQVON-ZDUSSCGKSA-N tert-butyl (7S)-12-oxo-14-(trifluoromethyl)-2,4,11-triazatetracyclo[11.4.0.02,6.07,11]heptadeca-1(17),3,5,13,15-pentaene-5-carboxylate Chemical compound C([C@H]1C=2N3C=NC=2C(=O)OC(C)(C)C)CCN1C(=O)C1=C3C=CC=C1C(F)(F)F WNNMAVYBIDQVON-ZDUSSCGKSA-N 0.000 description 1
- RABMNWTVQXGRIZ-AWEZNQCLSA-N tert-butyl (7S)-13-ethyl-11-oxo-2,4,10-triazatetracyclo[10.4.0.02,6.07,10]hexadeca-1(16),3,5,12,14-pentaene-5-carboxylate Chemical compound O=C1N2CC[C@H]2C2=C(C(=O)OC(C)(C)C)N=CN2C2=C1C(CC)=CC=C2 RABMNWTVQXGRIZ-AWEZNQCLSA-N 0.000 description 1
- NPRHJHZWJXUBAC-ZDUSSCGKSA-N tert-butyl (7S)-14-chloro-12-oxo-2,4,11-triazatetracyclo[11.4.0.02,6.07,11]heptadeca-1(17),3,5,13,15-pentaene-5-carboxylate Chemical compound O=C1C2=C(Cl)C=CC=C2N2C=NC(C(=O)OC(C)(C)C)=C2[C@@H]2CCCN21 NPRHJHZWJXUBAC-ZDUSSCGKSA-N 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- ZKLMHDHPWGLFHO-UHFFFAOYSA-N tert.butyl 8-chloro-11,13a-dihydro-9-oxo-9h-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate Chemical compound O=C1C2=C(Cl)C=CC=C2N2C=NC(C(=O)OC(C)(C)C)=C2C2C=CCN21 ZKLMHDHPWGLFHO-UHFFFAOYSA-N 0.000 description 1
- 150000003571 thiolactams Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
- C07D265/26—Two oxygen atoms, e.g. isatoic anhydride
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—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
- C07D487/04—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
- C07D487/12—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 three hetero rings
- C07D487/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH133981 | 1981-02-27 | ||
| CH133881 | 1981-02-27 | ||
| CH134181 | 1981-02-27 | ||
| CH134281 | 1981-02-27 | ||
| CH133881 | 1981-02-27 | ||
| CH133981 | 1981-02-27 | ||
| CH134281 | 1981-02-27 | ||
| CH134181 | 1981-02-27 | ||
| CH367581 | 1981-06-04 | ||
| CH367581 | 1981-06-04 | ||
| CH793481 | 1981-12-11 | ||
| CH793481 | 1981-12-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK74282A DK74282A (da) | 1982-08-28 |
| DK168073B1 true DK168073B1 (da) | 1994-01-31 |
Family
ID=27543637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK074282A DK168073B1 (da) | 1981-02-27 | 1982-02-19 | Analogifremgangsmaade til fremstilling af imidazodiazepiner eller farmaceutisk acceptable syreadditionssalte deraf |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4353827A (cs) |
| EP (1) | EP0059391B1 (cs) |
| KR (1) | KR890002624B1 (cs) |
| AU (1) | AU551891B2 (cs) |
| BR (1) | BR8201024A (cs) |
| CA (1) | CA1185602A (cs) |
| CS (1) | CS247064B2 (cs) |
| DE (1) | DE3263633D1 (cs) |
| DK (1) | DK168073B1 (cs) |
| FI (1) | FI73430C (cs) |
| HK (1) | HK23288A (cs) |
| IE (1) | IE52543B1 (cs) |
| IL (1) | IL65056A0 (cs) |
| MC (1) | MC1442A1 (cs) |
| NO (1) | NO157620C (cs) |
| NZ (1) | NZ199793A (cs) |
| PH (1) | PH19881A (cs) |
| PT (1) | PT74504B (cs) |
| YU (1) | YU45860B (cs) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MC1528A1 (fr) * | 1982-07-21 | 1984-04-13 | Hoffmann La Roche | Imidazobenzodiazepines |
| IL74070A (en) * | 1984-01-19 | 1988-12-30 | Hoffmann La Roche | Imidazodiazepine derivatives,their manufacture and pharmaceutical compositions containing them |
| DK174086D0 (da) * | 1986-04-16 | 1986-04-16 | Ferrosan As | Nye benzodiazepinderivater samt fremgangsmaade til fremstilling af samme |
| CA1327008C (en) * | 1988-01-15 | 1994-02-15 | Walter Merz | Anti-psychotic imidazobenzodiazepine |
| CA1312825C (en) * | 1988-01-27 | 1993-01-19 | F. Hoffmann-La Roche Ag | Prevention or interruption of panic states with an imidazobenzodiazepine |
| CA2015336A1 (en) * | 1989-05-19 | 1990-11-19 | F. Hoffmann-La Roche Ag | Imidazodiazepines for the treatment of neurological symptoms |
| CA2055308A1 (en) * | 1990-11-29 | 1992-05-30 | Roman Amrein | Imidazobenzodiazepine for the treatment of sleep disorders |
| JO2259B1 (en) * | 1999-05-12 | 2004-10-07 | اف. هوفمان- لاروش أيه جي | Method for the manufacture of diazapine derivatives |
| US7678818B2 (en) * | 2006-02-07 | 2010-03-16 | Hoffmann-La Roche Inc. | Anthranilamide and 2-amino-heteroarene-carboxamide compounds |
| KR101589314B1 (ko) | 2007-08-20 | 2016-01-28 | 에보텍 인터내셔널 게엠베하 | 수면 장애의 치료 |
| US20090054412A1 (en) * | 2007-08-20 | 2009-02-26 | John Alan Kemp | Treatment of Sleep Disorders |
| KR101671360B1 (ko) | 2010-04-15 | 2016-11-01 | 시애틀 지네틱스, 인크. | 표적화된 피롤로벤조디아제핀 접합체 |
| MX368648B (es) | 2010-04-15 | 2019-10-09 | Seattle Genetics Inc | Pirrolobenzodiazepinas usadas para tratar enfermedades proliferativas. |
| EA027971B1 (ru) | 2011-09-20 | 2017-09-29 | Медимьюн Лимитед | Пирролбензодиазепины |
| CA2850264C (en) | 2011-10-14 | 2019-11-05 | Spirogen Sarl | Pyrrolobenzodiazepines |
| WO2013055993A1 (en) | 2011-10-14 | 2013-04-18 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines and targeted conjugates |
| US9526798B2 (en) | 2011-10-14 | 2016-12-27 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines and targeted conjugates |
| BR112014008888A2 (pt) | 2011-10-14 | 2017-04-18 | Seattle Genetics Inc | pirrolobenzodiazepinas |
| CN103374000B (zh) * | 2012-04-13 | 2015-11-11 | 中国科学院广州生物医药与健康研究院 | 嘧啶并二氮杂卓类化合物及其药用组合物和应用 |
| BR112015008173A2 (pt) | 2012-10-12 | 2017-11-28 | Adc Therapeutics Sarl | conjugados de pirrolobenzodiazepina-anticorpo anti-psma |
| US10695433B2 (en) | 2012-10-12 | 2020-06-30 | Medimmune Limited | Pyrrolobenzodiazepine-antibody conjugates |
| DK2766048T3 (en) | 2012-10-12 | 2015-03-02 | Spirogen Sarl | PYRROLOBENZODIAZEPINS AND CONJUGATES THEREOF |
| CA2885305C (en) | 2012-10-12 | 2019-11-12 | Spirogen Sarl | Synthesis and intermediates of pyrrolobenzodiazepine derivatives for conjugation |
| RS56520B1 (sr) | 2012-10-12 | 2018-02-28 | Adc Therapeutics Sa | Pirolobenzodiazepin-anti-cd22 konjugati antitela |
| LT2906298T (lt) | 2012-10-12 | 2018-12-27 | Adc Therapeutics Sa | Pirolbenzodiazepino-antikūno konjugatai |
| WO2014057114A1 (en) | 2012-10-12 | 2014-04-17 | Adc Therapeutics Sàrl | Pyrrolobenzodiazepine-anti-psma antibody conjugates |
| NZ707543A (en) | 2012-10-12 | 2018-09-28 | Adc Therapeutics Sa | Pyrrolobenzodiazepine-antibody conjugates |
| EP3470086B1 (en) | 2012-10-12 | 2020-11-25 | Medimmune Limited | Pyrrolobenzodiazepines and conjugates thereof |
| 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 |
| EP3054983B1 (en) | 2013-10-11 | 2019-03-20 | Medimmune Limited | Pyrrolobenzodiazepine-antibody conjugates |
| WO2015052534A1 (en) | 2013-10-11 | 2015-04-16 | Spirogen Sàrl | Pyrrolobenzodiazepine-antibody conjugates |
| US9956299B2 (en) | 2013-10-11 | 2018-05-01 | Medimmune Limited | Pyrrolobenzodiazepine—antibody conjugates |
| GB201416112D0 (en) | 2014-09-12 | 2014-10-29 | Medimmune Ltd | Pyrrolobenzodiazepines and conjugates thereof |
| AU2015352545B2 (en) | 2014-11-25 | 2020-10-15 | 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 |
| 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 |
| GB201617466D0 (en) | 2016-10-14 | 2016-11-30 | Medimmune Ltd | Pyrrolobenzodiazepine conjugates |
| KR102181375B1 (ko) | 2017-02-08 | 2020-11-25 | 에이디씨 테라퓨틱스 에스에이 | 피롤로벤조디아제핀-항체 컨주게이트 |
| GB201702031D0 (en) | 2017-02-08 | 2017-03-22 | Medlmmune Ltd | Pyrrolobenzodiazepine-antibody conjugates |
| HUE059828T2 (hu) | 2017-04-18 | 2023-01-28 | Medimmune Ltd | Pirrolobenzodiazepin konjugátumok |
| BR112019021880A2 (pt) | 2017-04-20 | 2020-06-02 | Adc Therapeutics Sa | Terapia de combinação com conjugado anticorpo anti-axl-droga |
| MX2019015042A (es) | 2017-06-14 | 2020-08-06 | Adc Therapeutics Sa | Regimen de dosificacion. |
| RS62928B1 (sr) | 2017-08-18 | 2022-03-31 | Medimmune Ltd | Konjugati pirolobenzodiazepina |
| 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 |
| BR112021018260A2 (pt) | 2019-03-15 | 2021-11-23 | Medimmune Ltd | Dímeros de azetidobenzodiazepina e conjugados compreendendo-os para uso no tratamento de câncer |
| WO2021113492A1 (en) * | 2019-12-06 | 2021-06-10 | Schrödinger, Inc. | Cyclic compounds and methods of using same |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3933794A (en) * | 1971-08-04 | 1976-01-20 | The Upjohn Company | 2-(2-Alkynylamino)-3H-1,4-benzodiazepines |
| GB1600600A (en) * | 1977-03-10 | 1981-10-21 | Diamond Shamrock Chem | Plasticiser compositions for use with synthetic resin polymers |
| US4118386A (en) * | 1977-04-04 | 1978-10-03 | Hoffmann-La Roche Inc. | Synthesis of imidazo[1,5-a]diazepine-3-carboxylates |
| CA1143728A (en) * | 1979-10-04 | 1983-03-29 | Max Gerecke | Imidazodiazepine derivatives |
-
1982
- 1982-01-21 CA CA000394685A patent/CA1185602A/en not_active Expired
- 1982-02-10 PH PH26851A patent/PH19881A/en unknown
- 1982-02-17 CS CS821081A patent/CS247064B2/cs unknown
- 1982-02-18 US US06/349,801 patent/US4353827A/en not_active Expired - Lifetime
- 1982-02-19 DE DE8282101273T patent/DE3263633D1/de not_active Expired
- 1982-02-19 DK DK074282A patent/DK168073B1/da not_active IP Right Cessation
- 1982-02-19 EP EP82101273A patent/EP0059391B1/de not_active Expired
- 1982-02-19 IL IL65056A patent/IL65056A0/xx not_active IP Right Cessation
- 1982-02-22 AU AU80669/82A patent/AU551891B2/en not_active Expired
- 1982-02-22 NZ NZ199793A patent/NZ199793A/en unknown
- 1982-02-25 FI FI820647A patent/FI73430C/fi not_active IP Right Cessation
- 1982-02-25 MC MC821577A patent/MC1442A1/xx unknown
- 1982-02-26 YU YU43682A patent/YU45860B/sh unknown
- 1982-02-26 BR BR8201024A patent/BR8201024A/pt unknown
- 1982-02-26 IE IE421/82A patent/IE52543B1/en not_active IP Right Cessation
- 1982-02-26 PT PT74504A patent/PT74504B/pt unknown
- 1982-02-26 KR KR8200862A patent/KR890002624B1/ko not_active Expired
- 1982-02-26 NO NO820622A patent/NO157620C/no unknown
-
1988
- 1988-03-30 HK HK232/88A patent/HK23288A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU551891B2 (en) | 1986-05-15 |
| FI820647L (fi) | 1982-08-28 |
| PT74504A (en) | 1982-03-01 |
| KR890002624B1 (ko) | 1989-07-20 |
| PT74504B (en) | 1984-11-26 |
| DK74282A (da) | 1982-08-28 |
| NO157620B (no) | 1988-01-11 |
| FI73430C (fi) | 1987-10-09 |
| HK23288A (en) | 1988-04-08 |
| KR830009105A (ko) | 1983-12-17 |
| YU43682A (en) | 1988-08-31 |
| AU8066982A (en) | 1982-09-02 |
| YU45860B (sh) | 1992-09-07 |
| PH19881A (en) | 1986-08-13 |
| BR8201024A (pt) | 1983-01-04 |
| US4353827A (en) | 1982-10-12 |
| IE820421L (en) | 1982-08-27 |
| IE52543B1 (en) | 1987-12-09 |
| NO157620C (no) | 1988-04-20 |
| CS247064B2 (en) | 1986-11-13 |
| DE3263633D1 (en) | 1985-06-13 |
| EP0059391A1 (de) | 1982-09-08 |
| MC1442A1 (fr) | 1982-12-06 |
| NZ199793A (en) | 1985-08-30 |
| EP0059391B1 (de) | 1985-05-08 |
| CA1185602A (en) | 1985-04-16 |
| IL65056A0 (en) | 1982-04-30 |
| FI73430B (fi) | 1987-06-30 |
| NO820622L (no) | 1982-08-30 |
Similar Documents
| Publication | Publication Date | Title |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AHS | Application shelved for other reasons than non-payment | ||
| AHB | Application shelved due to non-payment | ||
| B1 | Patent granted (law 1993) | ||
| PUP | Patent expired |