ES2446358T3 - Derivados de imidazo[4,5-c]quinolina como inhibidores de los bromodominios - Google Patents
Derivados de imidazo[4,5-c]quinolina como inhibidores de los bromodominios Download PDFInfo
- Publication number
- ES2446358T3 ES2446358T3 ES10771770.4T ES10771770T ES2446358T3 ES 2446358 T3 ES2446358 T3 ES 2446358T3 ES 10771770 T ES10771770 T ES 10771770T ES 2446358 T3 ES2446358 T3 ES 2446358T3
- Authority
- ES
- Spain
- Prior art keywords
- dimethyl
- isoxazolyl
- methyloxy
- compound
- imidazo
- 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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- 102000001805 Bromodomains Human genes 0.000 title description 23
- 108050009021 Bromodomains Proteins 0.000 title description 21
- 239000003112 inhibitor Substances 0.000 title description 16
- ITIRVXDSMXFTPW-UHFFFAOYSA-N 1H-imidazo[4,5-c]quinoline Chemical class C1=CC=CC2=C(NC=N3)C3=CN=C21 ITIRVXDSMXFTPW-UHFFFAOYSA-N 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 236
- 150000003839 salts Chemical class 0.000 claims abstract description 95
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
- 239000001257 hydrogen Substances 0.000 claims abstract description 28
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 229910052705 radium Inorganic materials 0.000 claims abstract description 6
- 229910052701 rubidium Inorganic materials 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims abstract description 4
- 229910052727 yttrium Inorganic materials 0.000 claims abstract description 4
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims abstract description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 3
- 229910003827 NRaRb Inorganic materials 0.000 claims abstract description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims abstract description 3
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- 238000011282 treatment Methods 0.000 claims description 33
- 239000008194 pharmaceutical composition Substances 0.000 claims description 26
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 8
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- 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
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- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 230000001363 autoimmune Effects 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 230000004968 inflammatory condition Effects 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 3
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- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- VUVUVNZRUGEAHB-CYBMUJFWSA-N 7-(3,5-dimethyl-4-isoxazolyl)-8-methoxy-1-[(1R)-1-(2-pyridinyl)ethyl]-3H-imidazo[4,5-c]quinolin-2-one Chemical compound C1([C@@H](C)N2C3=C4C=C(C(=CC4=NC=C3NC2=O)C2=C(ON=C2C)C)OC)=CC=CC=N1 VUVUVNZRUGEAHB-CYBMUJFWSA-N 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- -1 * R2a represents: H Chemical group 0.000 abstract description 203
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 275
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
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- 210000004027 cell Anatomy 0.000 description 22
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 21
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- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 20
- 238000001819 mass spectrum Methods 0.000 description 20
- 201000010099 disease Diseases 0.000 description 19
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- 238000005481 NMR spectroscopy Methods 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 14
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Classifications
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- 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
- C07D471/02—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 two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0919423 | 2009-11-05 | ||
| GBGB0919423.4A GB0919423D0 (en) | 2009-11-05 | 2009-11-05 | Novel compounds |
| PCT/EP2010/066699 WO2011054846A1 (en) | 2009-11-05 | 2010-11-03 | Imidazo [4, 5-c] quinoline derivates as bromodomain inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2446358T3 true ES2446358T3 (es) | 2014-03-07 |
Family
ID=41501966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10771770.4T Active ES2446358T3 (es) | 2009-11-05 | 2010-11-03 | Derivados de imidazo[4,5-c]quinolina como inhibidores de los bromodominios |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8557984B2 (https=) |
| EP (1) | EP2496576B1 (https=) |
| JP (1) | JP5766708B2 (https=) |
| ES (1) | ES2446358T3 (https=) |
| GB (1) | GB0919423D0 (https=) |
| WO (1) | WO2011054846A1 (https=) |
Families Citing this family (145)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2571875A4 (en) | 2010-05-14 | 2013-10-30 | Dana Farber Cancer Inst Inc | CONTRACEPTIVE COMPOSITIONS FOR MEN AND METHODS OF USE THEREOF |
| MX354217B (es) | 2010-05-14 | 2018-02-19 | Dana Farber Cancer Inst Inc | Composiciones y metodos para el tratamiento de leucemia. |
| PL2902030T3 (pl) | 2010-05-14 | 2017-07-31 | Dana-Farber Cancer Institute, Inc. | Związki tienotriazolodiazepinowe do leczenia nowotworu |
| US20130225524A1 (en) * | 2010-11-05 | 2013-08-29 | Deping Chai | Chemical Compounds |
| WO2012075456A1 (en) | 2010-12-02 | 2012-06-07 | Constellation Pharmaceuticals | Bromodomain inhibitors and uses thereof |
| AR084070A1 (es) | 2010-12-02 | 2013-04-17 | Constellation Pharmaceuticals Inc | Inhibidores del bromodominio y usos de los mismos |
| US20130310374A1 (en) * | 2010-12-06 | 2013-11-21 | Piramal Enterprises Limited` | Substituted Imidazoquinoline Derivatives |
| US9422292B2 (en) | 2011-05-04 | 2016-08-23 | Constellation Pharmaceuticals, Inc. | Bromodomain inhibitors and uses thereof |
| WO2012174487A2 (en) | 2011-06-17 | 2012-12-20 | Constellation Pharmaceuticals, Inc. | Bromodomain inhibitors and uses thereof |
| GB201114103D0 (en) | 2011-08-17 | 2011-09-28 | Glaxosmithkline Llc | Novel compounds |
| WO2013027168A1 (en) | 2011-08-22 | 2013-02-28 | Pfizer Inc. | Novel heterocyclic compounds as bromodomain inhibitors |
| WO2013033269A1 (en) * | 2011-08-29 | 2013-03-07 | Coferon, Inc. | Bioorthogonal monomers capable of dimerizing and targeting bromodomains and methods of using same |
| RU2628074C2 (ru) | 2011-09-30 | 2017-08-14 | Си энд Си РИСЕРЧ ЛЭБОРЕТРИЗ | ТРИЦИКЛИЧЕСКИЕ АЗОТСОДЕРЖАЩИЕ ПРОИЗВОДНЫЕ ИМИДАЗО[4,5-с]ПИРИДИНА, ОБЛАДАЮЩИЕ ИНГИБИРУЮЩЕЙ АКТИВНОСТЬЮ В ОТНОШЕНИИ РЕЦЕПТОРА ГИСТАМИНА 4 (hH4R) |
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-
2010
- 2010-11-03 US US13/503,722 patent/US8557984B2/en not_active Expired - Fee Related
- 2010-11-03 WO PCT/EP2010/066699 patent/WO2011054846A1/en not_active Ceased
- 2010-11-03 ES ES10771770.4T patent/ES2446358T3/es active Active
- 2010-11-03 JP JP2012537382A patent/JP5766708B2/ja not_active Expired - Fee Related
- 2010-11-03 EP EP10771770.4A patent/EP2496576B1/en not_active Not-in-force
Also Published As
| Publication number | Publication date |
|---|---|
| EP2496576B1 (en) | 2013-12-18 |
| GB0919423D0 (en) | 2009-12-23 |
| WO2011054846A1 (en) | 2011-05-12 |
| JP5766708B2 (ja) | 2015-08-19 |
| EP2496576A1 (en) | 2012-09-12 |
| US20120232074A1 (en) | 2012-09-13 |
| US8557984B2 (en) | 2013-10-15 |
| JP2013510124A (ja) | 2013-03-21 |
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