DK2646446T3 - Bromodomain Inhibitors and Uses thereof - Google Patents

Info

Publication number

DK2646446T3

DK2646446T3 DK11844513.9T DK11844513T DK2646446T3 DK 2646446 T3 DK2646446 T3 DK 2646446T3 DK 11844513 T DK11844513 T DK 11844513T DK 2646446 T3 DK2646446 T3 DK 2646446T3

Authority

DK

Denmark

Prior art keywords

cancer

optionally substituted

mmol

compound

chlorophenyl

Prior art date

2010-12-02

Links

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• 102000001805 Bromodomains Human genes 0.000 title description 52
• 239000003112 inhibitor Substances 0.000 title description 24
• 108050009021 Bromodomains Proteins 0.000 title description 8
• 150000001875 compounds Chemical class 0.000 claims description 297
• 239000000203 mixture Substances 0.000 claims description 91
• -1 5-chloropyridin-2-yl Chemical group 0.000 claims description 90
• 125000001072 heteroaryl group Chemical group 0.000 claims description 88
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 77
• 125000000623 heterocyclic group Chemical group 0.000 claims description 75
• 208000035475 disorder Diseases 0.000 claims description 41
• 229910052739 hydrogen Inorganic materials 0.000 claims description 40
• 239000001257 hydrogen Substances 0.000 claims description 40
• 229910052736 halogen Inorganic materials 0.000 claims description 37
• 201000010099 disease Diseases 0.000 claims description 36
• 150000002367 halogens Chemical class 0.000 claims description 35
• 238000011282 treatment Methods 0.000 claims description 35
• 206010028980 Neoplasm Diseases 0.000 claims description 34
• 125000000217 alkyl group Chemical group 0.000 claims description 34
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
• 150000003839 salts Chemical class 0.000 claims description 29
• 150000002431 hydrogen Chemical class 0.000 claims description 26
• 125000001424 substituent group Chemical group 0.000 claims description 23
• 201000011510 cancer Diseases 0.000 claims description 17
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 230000002062 proliferating effect Effects 0.000 claims description 9
• 239000002671 adjuvant Substances 0.000 claims description 8
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 8
• 208000027866 inflammatory disease Diseases 0.000 claims description 7
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 206010040047 Sepsis Diseases 0.000 claims description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 5
• 201000009030 Carcinoma Diseases 0.000 claims description 4
• 208000007913 Pituitary Neoplasms Diseases 0.000 claims description 4
• 208000036142 Viral infection Diseases 0.000 claims description 4
• 206010044412 transitional cell carcinoma Diseases 0.000 claims description 4
• 230000009385 viral infection Effects 0.000 claims description 4
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 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
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
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• 208000018084 Bone neoplasm Diseases 0.000 claims description 3
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• 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 3
• 208000032612 Glial tumor Diseases 0.000 claims description 3
• 206010018338 Glioma Diseases 0.000 claims description 3
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• 206010039491 Sarcoma Diseases 0.000 claims description 3
• 206010041067 Small cell lung cancer Diseases 0.000 claims description 3
• 208000005718 Stomach Neoplasms Diseases 0.000 claims description 3
• 208000009956 adenocarcinoma Diseases 0.000 claims description 3
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
• 201000004101 esophageal cancer Diseases 0.000 claims description 3
• 206010017758 gastric cancer Diseases 0.000 claims description 3
• 125000001188 haloalkyl group Chemical group 0.000 claims description 3
• 201000002313 intestinal cancer Diseases 0.000 claims description 3
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 3
• 208000000587 small cell lung carcinoma Diseases 0.000 claims description 3
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• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 3
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• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([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
• 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 2
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 2
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• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
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• 208000017604 Hodgkin disease Diseases 0.000 claims description 2
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• 208000005016 Intestinal Neoplasms Diseases 0.000 claims description 2
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• 208000003445 Mouth Neoplasms Diseases 0.000 claims description 2
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 2
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• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
• 201000010881 cervical cancer Diseases 0.000 claims description 2
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• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
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• 201000003741 Gastrointestinal carcinoma Diseases 0.000 claims 1
• 208000000389 T-cell leukemia Diseases 0.000 claims 1
• 208000028530 T-cell lymphoblastic leukemia/lymphoma Diseases 0.000 claims 1
• 230000001154 acute effect Effects 0.000 claims 1
• 208000025113 myeloid leukemia Diseases 0.000 claims 1
• 210000001328 optic nerve Anatomy 0.000 claims 1
• 201000011096 spinal cancer Diseases 0.000 claims 1
• 208000014618 spinal cord cancer Diseases 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 264
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 137
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• 229920006395 saturated elastomer Polymers 0.000 description 96
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 93
• 239000011593 sulfur Chemical group 0.000 description 93
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 91
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• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 88
• 238000006243 chemical reaction Methods 0.000 description 86
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 86
• 238000000034 method Methods 0.000 description 73
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• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
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• 102100029894 Bromodomain testis-specific protein Human genes 0.000 description 28
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