JP4520411B2 - ピロロ［２，１−ｃ］［１，４］ベンゾジアゼピン・ハイブリッドの調製方法 - Google Patents
ピロロ［２，１−ｃ］［１，４］ベンゾジアゼピン・ハイブリッドの調製方法 Download PDFInfo
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- JP4520411B2 JP4520411B2 JP2005512761A JP2005512761A JP4520411B2 JP 4520411 B2 JP4520411 B2 JP 4520411B2 JP 2005512761 A JP2005512761 A JP 2005512761A JP 2005512761 A JP2005512761 A JP 2005512761A JP 4520411 B2 JP4520411 B2 JP 4520411B2
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- JP
- Japan
- Prior art keywords
- general formula
- pyrrolo
- benzo
- imidazol
- methoxy
- 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.)
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- MSNVESLISHTIRS-UHFFFAOYSA-N 9h-pyrrolo[2,1-c][1,4]benzodiazepine Chemical compound N1=C2C=CC=CC2=CN2CC=CC2=C1 MSNVESLISHTIRS-UHFFFAOYSA-N 0.000 title claims description 32
- 238000000034 method Methods 0.000 title claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 80
- -1 1H-benzo [d] imidazol-2-yl Chemical group 0.000 claims description 33
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 30
- CRMGITHMNVPUPY-UHFFFAOYSA-N 2-[ethoxy(ethylsulfanyl)methyl]pyrrolidine Chemical compound CCOC(SCC)C1CCCN1 CRMGITHMNVPUPY-UHFFFAOYSA-N 0.000 claims description 23
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 18
- 239000003960 organic solvent Substances 0.000 claims description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 8
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- REOGMBVECOGANJ-UHFFFAOYSA-N chembl377740 Chemical compound C1=CC(O)=CC=C1C1=NC2=CC=CC=C2N1 REOGMBVECOGANJ-UHFFFAOYSA-N 0.000 claims description 6
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- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
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- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 claims description 2
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
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- 239000000243 solution Substances 0.000 description 23
- PWDSJBHSKYBUEX-UHFFFAOYSA-N 1,4-benzodiazepin-5-one Chemical compound O=C1N=CC=NC2=CC=CC=C12 PWDSJBHSKYBUEX-UHFFFAOYSA-N 0.000 description 21
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- LQDGLTOVYOUCRG-QMMMGPOBSA-N (6as)-3-hydroxy-2-methoxy-6a,7,8,9-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-11-one Chemical class N1=C[C@@H]2CCCN2C(=O)C2=C1C=C(O)C(OC)=C2 LQDGLTOVYOUCRG-QMMMGPOBSA-N 0.000 description 3
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- IOOMXAQUNPWDLL-UHFFFAOYSA-N 2-[6-(diethylamino)-3-(diethyliminiumyl)-3h-xanthen-9-yl]-5-sulfobenzene-1-sulfonate Chemical compound C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S(O)(=O)=O)C=C1S([O-])(=O)=O IOOMXAQUNPWDLL-UHFFFAOYSA-N 0.000 description 2
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- OMRPLUKQNWNZAV-CONSDPRKSA-N (6as)-3-[3-[[(6as)-2-methoxy-8-(4-methoxyphenyl)-11-oxo-6a,7-dihydropyrrolo[2,1-c][1,4]benzodiazepin-3-yl]oxy]propoxy]-8-(4-aminophenyl)-2-methoxy-6a,7-dihydropyrrolo[2,1-c][1,4]benzodiazepin-11-one Chemical compound C1=CC(OC)=CC=C1C1=CN2C(=O)C3=CC(OC)=C(OCCCOC=4C(=CC=5C(=O)N6C=C(C[C@H]6C=NC=5C=4)C=4C=CC(N)=CC=4)OC)C=C3N=C[C@@H]2C1 OMRPLUKQNWNZAV-CONSDPRKSA-N 0.000 description 1
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- YUOCYTRGANSSRY-UHFFFAOYSA-N pyrrolo[2,3-i][1,2]benzodiazepine Chemical compound C1=CN=NC2=C3C=CN=C3C=CC2=C1 YUOCYTRGANSSRY-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IN2003/000462 WO2005063759A1 (fr) | 2003-12-31 | 2003-12-31 | Procede servant a preparer des hybrides de pyrrolo[2, 1-c] [1, 4] benzodiazepine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007528343A JP2007528343A (ja) | 2007-10-11 |
| JP4520411B2 true JP4520411B2 (ja) | 2010-08-04 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2005512761A Expired - Fee Related JP4520411B2 (ja) | 2003-12-31 | 2003-12-31 | ピロロ［２，１−ｃ］［１，４］ベンゾジアゼピン・ハイブリッドの調製方法 |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP4520411B2 (fr) |
| AU (1) | AU2003300718A1 (fr) |
| GB (1) | GB2424883B (fr) |
| WO (1) | WO2005063759A1 (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5149193B2 (ja) * | 2005-11-10 | 2013-02-20 | カウンスィル オブ サイエンティフィック アンド インダストリアル リサーチ | 新規なピロロ［２，１−ｃ］［１，４］ベンゾジアゼピンハイブリッドおよびその調製のための方法 |
| US8063204B2 (en) | 2007-02-13 | 2011-11-22 | Council Of Scientific & Industrial Research | Benzothiazole and benzoxazole linked pyrrolo[2,1-c] [1, 4] benzodiazepine hybrids as novel antitumour agents and process for the preparation thereof |
| GB2469980B (en) * | 2008-03-05 | 2012-02-22 | Council Scient Ind Res | Naphthalimide-benzimidazole hybrids as potential antitumour agents and process for the preparation thereof |
| WO2009113085A1 (fr) * | 2008-03-11 | 2009-09-17 | Council Of Scientific & Industrial Research | Nouveaux hybrides de pyrrolo[2,1-q[1,4] benzodiazépine liés au un cycle benzimidazole en tant qu’agents anti-tumoraux et leurs procédés de préparation |
| EP2271648B1 (fr) | 2008-03-26 | 2013-02-13 | Council of Scientific & Industrial Research | Hybrides de pyrrolo [2,1-c][1,4]benzodiazépine liés à l'isoxazoline en tant qu'agents anti-cancéreux potentiels et leurs procédés de fabrication |
| US8592407B2 (en) | 2008-11-19 | 2013-11-26 | Council Of Scientific & Industrial Research | Pyrrolo[2,1-c][1,4] benzodiazepine derivatives with dithiocarbamate side chains and process for the preparation thereof |
| PL3325482T3 (pl) | 2015-07-21 | 2021-01-11 | Immunogen, Inc. | Sposoby otrzymywania cytotoksycznych pochodnych benzodiazepiny |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2244210T3 (es) * | 1998-08-27 | 2005-12-01 | Spirogen Limited | Pirrolobenzodiazepinas. |
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2003
- 2003-12-31 GB GB0614750A patent/GB2424883B/en not_active Expired - Fee Related
- 2003-12-31 AU AU2003300718A patent/AU2003300718A1/en not_active Abandoned
- 2003-12-31 JP JP2005512761A patent/JP4520411B2/ja not_active Expired - Fee Related
- 2003-12-31 WO PCT/IN2003/000462 patent/WO2005063759A1/fr active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| GB2424883A (en) | 2006-10-11 |
| WO2005063759A1 (fr) | 2005-07-14 |
| GB0614750D0 (en) | 2006-09-06 |
| JP2007528343A (ja) | 2007-10-11 |
| GB2424883B (en) | 2008-10-22 |
| AU2003300718A1 (en) | 2005-07-21 |
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