JP2015512939A5 - - Google Patents
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- Publication number
- JP2015512939A5 JP2015512939A5 JP2015505789A JP2015505789A JP2015512939A5 JP 2015512939 A5 JP2015512939 A5 JP 2015512939A5 JP 2015505789 A JP2015505789 A JP 2015505789A JP 2015505789 A JP2015505789 A JP 2015505789A JP 2015512939 A5 JP2015512939 A5 JP 2015512939A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- dihydro
- hydroxyacrylamide
- hydroxyamino
- ethyl
- 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.)
- Granted
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- -1 N-hydroxyaminocarbonyl Chemical group 0.000 claims description 74
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 4
- DWWXXRKGLLUOGK-YRNVUSSQSA-N (e)-3-[2-ethyl-3-[2-(4-methoxyphenyl)ethyl]-4-oxoquinazolin-7-yl]-n-hydroxyprop-2-enamide Chemical compound CCC1=NC2=CC(\C=C\C(=O)NO)=CC=C2C(=O)N1CCC1=CC=C(OC)C=C1 DWWXXRKGLLUOGK-YRNVUSSQSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 238000000034 method Methods 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
- 206010028980 Neoplasm Diseases 0.000 claims 9
- 201000011510 cancer Diseases 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 4
- 230000003013 cytotoxicity Effects 0.000 claims 4
- 231100000135 cytotoxicity Toxicity 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 230000001939 inductive effect Effects 0.000 claims 4
- 239000003937 drug carrier Substances 0.000 claims 3
- 230000002401 inhibitory effect Effects 0.000 claims 3
- 239000003981 vehicle Substances 0.000 claims 3
- DROCPQHWNIUOQA-CSKARUKUSA-N (e)-3-(3-benzyl-2-methyl-4-oxoquinazolin-7-yl)-n-hydroxyprop-2-enamide Chemical compound CC1=NC2=CC(\C=C\C(=O)NO)=CC=C2C(=O)N1CC1=CC=CC=C1 DROCPQHWNIUOQA-CSKARUKUSA-N 0.000 claims 2
- KOGSPXQDGNAZKQ-YRNVUSSQSA-N (e)-3-[2-cyclopropyl-4-oxo-3-(2-phenylethyl)quinazolin-7-yl]-n-hydroxyprop-2-enamide Chemical compound C=1C(/C=C/C(=O)NO)=CC=C(C(N2CCC=3C=CC=CC=3)=O)C=1N=C2C1CC1 KOGSPXQDGNAZKQ-YRNVUSSQSA-N 0.000 claims 2
- HKISHKJJYBCZQL-UXBLZVDNSA-N (e)-3-[2-ethyl-3-[2-(4-fluorophenyl)ethyl]-4-oxoquinazolin-7-yl]-n-hydroxyprop-2-enamide Chemical compound CCC1=NC2=CC(\C=C\C(=O)NO)=CC=C2C(=O)N1CCC1=CC=C(F)C=C1 HKISHKJJYBCZQL-UXBLZVDNSA-N 0.000 claims 2
- AULBTEVAVDTQLP-PKNBQFBNSA-N (e)-3-[2-ethyl-4-oxo-3-(2-phenylethyl)quinazolin-7-yl]-n-hydroxyprop-2-enamide Chemical compound CCC1=NC2=CC(\C=C\C(=O)NO)=CC=C2C(=O)N1CCC1=CC=CC=C1 AULBTEVAVDTQLP-PKNBQFBNSA-N 0.000 claims 2
- OSGSDDYIACXJCX-ACCUITESSA-N (e)-3-[2-ethyl-4-oxo-3-(3-phenylpropyl)quinazolin-7-yl]-n-hydroxyprop-2-enamide Chemical compound CCC1=NC2=CC(\C=C\C(=O)NO)=CC=C2C(=O)N1CCCC1=CC=CC=C1 OSGSDDYIACXJCX-ACCUITESSA-N 0.000 claims 2
- KUKBDBQCXIHWRC-ZHACJKMWSA-N (e)-n-hydroxy-3-(2-methyl-4-oxo-3-phenylquinazolin-5-yl)prop-2-enamide Chemical compound CC1=NC2=CC=CC(\C=C\C(=O)NO)=C2C(=O)N1C1=CC=CC=C1 KUKBDBQCXIHWRC-ZHACJKMWSA-N 0.000 claims 2
- JNOVVOHLHNGPOH-CSKARUKUSA-N (e)-n-hydroxy-3-(2-methyl-4-oxo-3-phenylquinazolin-6-yl)prop-2-enamide Chemical compound CC1=NC2=CC=C(\C=C\C(=O)NO)C=C2C(=O)N1C1=CC=CC=C1 JNOVVOHLHNGPOH-CSKARUKUSA-N 0.000 claims 2
- MDTWRJDWPUJHKT-CSKARUKUSA-N (e)-n-hydroxy-3-(2-methyl-4-oxo-3-phenylquinazolin-7-yl)prop-2-enamide Chemical compound CC1=NC2=CC(\C=C\C(=O)NO)=CC=C2C(=O)N1C1=CC=CC=C1 MDTWRJDWPUJHKT-CSKARUKUSA-N 0.000 claims 2
- STSNTVHQAOSMDW-ZHACJKMWSA-N (e)-n-hydroxy-3-(2-methyl-4-oxo-3-phenylquinazolin-8-yl)prop-2-enamide Chemical compound CC1=NC2=C(\C=C\C(=O)NO)C=CC=C2C(=O)N1C1=CC=CC=C1 STSNTVHQAOSMDW-ZHACJKMWSA-N 0.000 claims 2
- NVEBAMFLYZFKKW-CSKARUKUSA-N (e)-n-hydroxy-3-[2-methyl-4-oxo-3-(2-phenylethyl)quinazolin-7-yl]prop-2-enamide Chemical compound CC1=NC2=CC(\C=C\C(=O)NO)=CC=C2C(=O)N1CCC1=CC=CC=C1 NVEBAMFLYZFKKW-CSKARUKUSA-N 0.000 claims 2
- SDVRJMHVMXPKQZ-PKNBQFBNSA-N (e)-n-hydroxy-3-[4-oxo-3-(2-phenylethyl)-2-propan-2-ylquinazolin-7-yl]prop-2-enamide Chemical compound CC(C)C1=NC2=CC(\C=C\C(=O)NO)=CC=C2C(=O)N1CCC1=CC=CC=C1 SDVRJMHVMXPKQZ-PKNBQFBNSA-N 0.000 claims 2
- VAAWIYIVFTYJRI-VQHVLOKHSA-N (e)-n-hydroxy-3-[4-oxo-3-(2-phenylethyl)quinazolin-7-yl]prop-2-enamide Chemical compound C=1C(/C=C/C(=O)NO)=CC=C(C2=O)C=1N=CN2CCC1=CC=CC=C1 VAAWIYIVFTYJRI-VQHVLOKHSA-N 0.000 claims 2
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims 2
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 206010029098 Neoplasm skin Diseases 0.000 claims 2
- 208000000453 Skin Neoplasms Diseases 0.000 claims 2
- 230000005907 cancer growth Effects 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 201000007270 liver cancer Diseases 0.000 claims 2
- 208000014018 liver neoplasm Diseases 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- RGKDACUEVSPDNA-CMDGGOBGSA-N (e)-3-[2-ethyl-6-fluoro-4-oxo-3-(2-phenylethyl)quinazolin-7-yl]-n-hydroxyprop-2-enamide Chemical compound CCC1=NC2=CC(\C=C\C(=O)NO)=C(F)C=C2C(=O)N1CCC1=CC=CC=C1 RGKDACUEVSPDNA-CMDGGOBGSA-N 0.000 claims 1
- NAMOJMZBPJZNOD-CMDGGOBGSA-N (e)-3-[2-ethyl-7-fluoro-4-oxo-3-(2-phenylethyl)quinazolin-6-yl]-n-hydroxyprop-2-enamide Chemical compound CCC1=NC2=CC(F)=C(\C=C\C(=O)NO)C=C2C(=O)N1CCC1=CC=CC=C1 NAMOJMZBPJZNOD-CMDGGOBGSA-N 0.000 claims 1
- WBEKWMCWJUVKEG-UHFFFAOYSA-N 2-[7-chloro-2-ethyl-4-oxo-3-(2-phenylethyl)quinazolin-6-yl]-N-hydroxyprop-2-enamide Chemical compound ClC1=C(C=C2C(N(C(=NC2=C1)CC)CCC1=CC=CC=C1)=O)C(C(=O)NO)=C WBEKWMCWJUVKEG-UHFFFAOYSA-N 0.000 claims 1
- VERZRJYONMSRFY-UHFFFAOYSA-N 4-[2-ethyl-4-oxo-3-(2-phenylethyl)quinazolin-8-yl]-n-hydroxybenzamide Chemical compound CCC1=NC2=C(C=3C=CC(=CC=3)C(=O)NO)C=CC=C2C(=O)N1CCC1=CC=CC=C1 VERZRJYONMSRFY-UHFFFAOYSA-N 0.000 claims 1
- VLBQAJZSHGGUBQ-UHFFFAOYSA-N 4-[[2-ethyl-4-oxo-3-(2-phenylethyl)quinazolin-6-yl]methyl]-n-hydroxybenzamide Chemical compound C1=C2C(=O)N(CCC=3C=CC=CC=3)C(CC)=NC2=CC=C1CC1=CC=C(C(=O)NO)C=C1 VLBQAJZSHGGUBQ-UHFFFAOYSA-N 0.000 claims 1
- LQAXATZNWUNYBS-UHFFFAOYSA-N 4-[[2-ethyl-4-oxo-3-(2-phenylethyl)quinazolin-7-yl]methyl]-n-hydroxybenzamide Chemical compound C=1C=C2C(=O)N(CCC=3C=CC=CC=3)C(CC)=NC2=CC=1CC1=CC=C(C(=O)NO)C=C1 LQAXATZNWUNYBS-UHFFFAOYSA-N 0.000 claims 1
- HPCPCLJRBNRLLW-UHFFFAOYSA-N 4-[[2-ethyl-4-oxo-3-(2-phenylethyl)quinazolin-8-yl]methyl]-n-hydroxybenzamide Chemical compound C1=CC=C2C(=O)N(CCC=3C=CC=CC=3)C(CC)=NC2=C1CC1=CC=C(C(=O)NO)C=C1 HPCPCLJRBNRLLW-UHFFFAOYSA-N 0.000 claims 1
- 208000036762 Acute promyelocytic leukaemia Diseases 0.000 claims 1
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims 1
- 208000036832 Adenocarcinoma of ovary Diseases 0.000 claims 1
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 1
- 201000009030 Carcinoma Diseases 0.000 claims 1
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 102000003964 Histone deacetylase Human genes 0.000 claims 1
- 108090000353 Histone deacetylase Proteins 0.000 claims 1
- 206010023774 Large cell lung cancer Diseases 0.000 claims 1
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 1
- 206010061328 Ovarian epithelial cancer Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 206010041067 Small cell lung cancer Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 230000010261 cell growth Effects 0.000 claims 1
- 230000003831 deregulation Effects 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 208000021045 exocrine pancreatic carcinoma Diseases 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 201000005249 lung adenocarcinoma Diseases 0.000 claims 1
- 201000009546 lung large cell carcinoma Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 208000013371 ovarian adenocarcinoma Diseases 0.000 claims 1
- 201000006588 ovary adenocarcinoma Diseases 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 201000001514 prostate carcinoma Diseases 0.000 claims 1
- 201000001475 prostate lymphoma Diseases 0.000 claims 1
- 208000023958 prostate neoplasm Diseases 0.000 claims 1
- 208000000587 small cell lung carcinoma Diseases 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 4
- ACMIJDVJWLMBCX-PXAZEXFGSA-N 4-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-6-fluoro-n-methyl-2-(2-methylpyrimidin-5-yl)oxy-9h-pyrimido[4,5-b]indol-8-amine Chemical compound CNC1=CC(F)=CC(C2=C(N3C[C@@H]4NCC[C@@H]4C3)N=3)=C1NC2=NC=3OC1=CN=C(C)N=C1 ACMIJDVJWLMBCX-PXAZEXFGSA-N 0.000 description 3
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 3
- 125000004442 acylamino group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 3
- 125000001589 carboacyl group Chemical group 0.000 description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 description 3
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 3
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- DRLAOVNZDDOIAG-CMDGGOBGSA-N (e)-3-[7-chloro-2-ethyl-4-oxo-3-(2-phenylethyl)quinazolin-6-yl]-n-hydroxyprop-2-enamide Chemical compound CCC1=NC2=CC(Cl)=C(\C=C\C(=O)NO)C=C2C(=O)N1CCC1=CC=CC=C1 DRLAOVNZDDOIAG-CMDGGOBGSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000005327 perimidinyl group Chemical group N1C(=NC2=CC=CC3=CC=CC1=C23)* 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004932 phenoxathinyl group Chemical group 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261622127P | 2012-04-10 | 2012-04-10 | |
| US61/622,127 | 2012-04-10 | ||
| PCT/US2013/035004 WO2013154870A1 (en) | 2012-04-10 | 2013-04-02 | Histone deacetylases (hdacs) inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015512939A JP2015512939A (ja) | 2015-04-30 |
| JP2015512939A5 true JP2015512939A5 (https=) | 2016-06-02 |
| JP6258918B2 JP6258918B2 (ja) | 2018-01-10 |
Family
ID=49292802
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015505789A Active JP6258918B2 (ja) | 2012-04-10 | 2013-04-02 | ヒストンデアセチラーゼ（ｈｄａｃｓ）阻害剤 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US9387209B2 (https=) |
| EP (1) | EP2836484B1 (https=) |
| JP (1) | JP6258918B2 (https=) |
| KR (1) | KR101781922B1 (https=) |
| CN (1) | CN104364237B (https=) |
| AU (1) | AU2013246278B2 (https=) |
| BR (1) | BR112014025122B1 (https=) |
| ES (1) | ES2630062T3 (https=) |
| IL (1) | IL235053A (https=) |
| IN (1) | IN2014MN02104A (https=) |
| RU (1) | RU2629947C2 (https=) |
| TW (1) | TWI481597B (https=) |
| WO (1) | WO2013154870A1 (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10052739B2 (en) | 2011-09-12 | 2018-08-21 | Applied Materials, Inc. | Carrier head with composite plastic portions |
| US8940742B2 (en) | 2012-04-10 | 2015-01-27 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| MX2021012208A (es) | 2013-10-04 | 2023-01-19 | Infinity Pharmaceuticals Inc | Compuestos heterocíclicos y usos de los mismos. |
| WO2015051241A1 (en) | 2013-10-04 | 2015-04-09 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| JP2017508798A (ja) | 2014-03-07 | 2017-03-30 | ザ ジョンズ ホプキンス ユニバーシティ | ヒストンリジン特異的デメチラーゼ（ｌｓｄ１）およびヒストンデアセチラーゼ（ｈｄａｃ）の阻害剤 |
| NZ724368A (en) | 2014-03-19 | 2023-07-28 | Infinity Pharmaceuticals Inc | Heterocyclic compounds for use in the treatment of pi3k-gamma mediated disorders |
| WO2015153516A1 (en) | 2014-04-04 | 2015-10-08 | University Of Florida Research Foundation | Hdac inhibitor compounds and methods of treatment |
| WO2016054491A1 (en) | 2014-10-03 | 2016-04-07 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| EP4585268A3 (en) | 2015-09-14 | 2025-10-15 | Twelve Therapeutics, Inc. | Solid forms of isoquinolinone derivatives, process of making, compositions comprising, and methods of using the same |
| US10759806B2 (en) | 2016-03-17 | 2020-09-01 | Infinity Pharmaceuticals, Inc. | Isotopologues of isoquinolinone and quinazolinone compounds and uses thereof as PI3K kinase inhibitors |
| WO2017214269A1 (en) | 2016-06-08 | 2017-12-14 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| CN110621317B (zh) * | 2017-05-16 | 2023-05-12 | 安基生技新药股份有限公司 | 组蛋白去乙酰化酶（hdacs）抑制剂 |
| GB201820450D0 (en) | 2018-12-14 | 2019-01-30 | Z Factor Ltd | Compound and its use for the treatment of alpha1-antitryspin deficiency |
| GB201918404D0 (en) * | 2019-12-13 | 2020-01-29 | Z Factor Ltd | Compounds and their use for the treatment of aplha1-antitrypsin deficiency |
| KR20210116830A (ko) * | 2020-03-17 | 2021-09-28 | 충북대학교 산학협력단 | 신규한 4-옥소퀴나졸린-기반 n-하이드록시프로펜아미드 및 이의 용도 |
| CN111517977B (zh) * | 2020-05-28 | 2023-05-23 | 爱斯特（成都）生物制药股份有限公司 | 一种合成2,4-二氟-3-三甲基乙酰胺基苯甲酸的方法 |
| JP2023530788A (ja) * | 2020-06-08 | 2023-07-19 | アンジー ファーマシューティカル カンパニー リミテッド | 選択的ｈｄａｃ６阻害剤として有用なキナゾリン誘導体 |
| WO2023159155A1 (en) * | 2022-02-18 | 2023-08-24 | Pivalent Therapeutics, Inc. | Inhibitors of phosphoinositide 3-kinase (pi3k) and uses thereof |
| IL326137A (en) | 2023-07-28 | 2026-03-01 | Cogent Biosciences Inc | PI3K inhibitors |
| AU2024364867A1 (en) * | 2023-10-18 | 2025-07-24 | Gilva Therapeutics Co., Ltd. | Quinazolinone derivatives for hdac inhibition |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE666424A (https=) * | 1965-05-12 | 1966-01-05 | ||
| FR6001M (https=) * | 1966-12-02 | 1968-04-29 | ||
| ZA705270B (en) * | 1969-08-02 | 1971-04-28 | Sumitomo Chemical Co | Novel quinazolinone derivatives and a process for production thereof |
| US4054658A (en) * | 1974-02-06 | 1977-10-18 | William H. Rorer, Inc. | Therapeutic compositions containing methaqualone |
| NZ192392A (en) | 1978-12-19 | 1983-02-15 | M Ishikawa | 3-(substituted (phenyl or pyridyl)) -3,4-dihydroquinazolin-4-ones |
| JP3488890B2 (ja) * | 1993-11-09 | 2004-01-19 | アグロカネショウ株式会社 | ３−ｎ−置換キナゾリノン誘導体、その製造法および該化合物を含有する除草剤 |
| AU2001248701A1 (en) * | 2000-03-24 | 2001-10-03 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| EP1524262A1 (en) * | 2000-03-24 | 2005-04-20 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| CA2502302A1 (en) * | 2002-11-04 | 2004-05-21 | Nps Pharmaceuticals, Inc. | Quinazolinone compounds as calcilytics |
| ITMI20041869A1 (it) | 2004-10-01 | 2005-01-01 | Dac Srl | Nuovi inibitori delle istone deacetilasi |
| WO2007011623A1 (en) * | 2005-07-15 | 2007-01-25 | Schering Corporation | Quinazoline derivatives useful in cancer treatment |
| CN101287706A (zh) | 2005-09-21 | 2008-10-15 | 尼科梅德有限责任公司 | 作为组蛋白脱乙酰基酶抑制剂的磺酰基吡咯盐酸盐 |
| GB0525068D0 (en) * | 2005-12-08 | 2006-01-18 | Novartis Ag | Organic compounds |
| GB0619753D0 (en) | 2006-10-06 | 2006-11-15 | Chroma Therapeutics Ltd | Enzyme inhibitors |
| GB0624187D0 (en) | 2006-12-04 | 2007-01-10 | Jackson William P | HDAC inhibitors |
| WO2008087514A2 (en) | 2007-01-17 | 2008-07-24 | Orchid Research Laboratories Limited | Hdac inhibitors |
| US20100261710A1 (en) | 2007-08-21 | 2010-10-14 | Arqule, Inc. | HDAC Inhibitors |
| JP5730575B2 (ja) | 2007-10-01 | 2015-06-10 | リクスト・バイオテクノロジー，インコーポレイテッド | Ｈｄａｃ阻害剤 |
| US8431538B2 (en) | 2009-07-22 | 2013-04-30 | The Board Of Trustees Of The University Of Illinois | HDAC inhibitors and therapeutic methods of using same |
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