NZ524365A - Hydroxamate derivatives useful as deacetylase inhibitors - Google Patents
Hydroxamate derivatives useful as deacetylase inhibitorsInfo
- Publication number
- NZ524365A NZ524365A NZ524365A NZ52436501A NZ524365A NZ 524365 A NZ524365 A NZ 524365A NZ 524365 A NZ524365 A NZ 524365A NZ 52436501 A NZ52436501 A NZ 52436501A NZ 524365 A NZ524365 A NZ 524365A
- Authority
- NZ
- New Zealand
- Prior art keywords
- alkyl
- aryl
- heteroaryl
- cycloalkyl
- substituted
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 341
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 161
- 150000001875 compounds Chemical class 0.000 claims abstract description 131
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 120
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 112
- -1 R2 is H Chemical group 0.000 claims abstract description 103
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 101
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract description 98
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 88
- 125000001424 substituent group Chemical group 0.000 claims abstract description 87
- 125000002252 acyl group Chemical group 0.000 claims abstract description 53
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims abstract description 50
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 44
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 43
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 41
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 40
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 16
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims abstract description 12
- 230000002062 proliferating effect Effects 0.000 claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims description 52
- 150000003839 salts Chemical class 0.000 claims description 51
- 210000004027 cell Anatomy 0.000 claims description 46
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 125000004122 cyclic group Chemical group 0.000 claims description 32
- 125000003282 alkyl amino group Chemical group 0.000 claims description 30
- 125000005842 heteroatom Chemical group 0.000 claims description 28
- 229910052760 oxygen Chemical group 0.000 claims description 28
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 25
- 125000002619 bicyclic group Chemical group 0.000 claims description 25
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 23
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
- 150000001721 carbon Chemical group 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 18
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 11
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 11
- 150000002825 nitriles Chemical class 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 210000004881 tumor cell Anatomy 0.000 claims description 9
- BWDQBBCUWLSASG-MDZDMXLPSA-N (e)-n-hydroxy-3-[4-[[2-hydroxyethyl-[2-(1h-indol-3-yl)ethyl]amino]methyl]phenyl]prop-2-enamide Chemical compound C=1NC2=CC=CC=C2C=1CCN(CCO)CC1=CC=C(\C=C\C(=O)NO)C=C1 BWDQBBCUWLSASG-MDZDMXLPSA-N 0.000 claims description 7
- 101100160255 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) YLR154C-H gene Proteins 0.000 claims description 7
- 230000006907 apoptotic process Effects 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 101150020251 NR13 gene Proteins 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 230000012010 growth Effects 0.000 claims description 6
- 125000006763 (C3-C9) cycloalkyl group Chemical group 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 239000001301 oxygen Chemical group 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 238000010186 staining Methods 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000004532 benzofuran-3-yl group Chemical group O1C=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- FPOHNWQLNRZRFC-ZHACJKMWSA-N panobinostat Chemical compound CC=1NC2=CC=CC=C2C=1CCNCC1=CC=C(\C=C\C(=O)NO)C=C1 FPOHNWQLNRZRFC-ZHACJKMWSA-N 0.000 claims description 4
- 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
- 241000124008 Mammalia Species 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 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
- 230000025084 cell cycle arrest Effects 0.000 claims description 2
- 210000002950 fibroblast Anatomy 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- ZLUZDKXBTNQWOL-MDZDMXLPSA-N (e)-n-hydroxy-3-[4-[[2-(1h-indol-3-yl)ethylamino]methyl]phenyl]prop-2-enamide Chemical compound C1=CC(/C=C/C(=O)NO)=CC=C1CNCCC1=CNC2=CC=CC=C12 ZLUZDKXBTNQWOL-MDZDMXLPSA-N 0.000 claims 3
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 2
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 230000033228 biological regulation Effects 0.000 claims 1
- 230000022131 cell cycle Effects 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 231100001160 nonlethal Toxicity 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
- 206010028980 Neoplasm Diseases 0.000 description 35
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- 102000003964 Histone deacetylase Human genes 0.000 description 17
- 108090000353 Histone deacetylase Proteins 0.000 description 17
- 239000000203 mixture Substances 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 13
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 101000711846 Homo sapiens Transcription factor SOX-9 Proteins 0.000 description 10
- 101100232371 Hordeum vulgare IAT3 gene Proteins 0.000 description 10
- 102100034204 Transcription factor SOX-9 Human genes 0.000 description 10
- 230000005764 inhibitory process Effects 0.000 description 10
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 9
- 229910004373 HOAc Inorganic materials 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 9
- 150000001412 amines Chemical group 0.000 description 8
- 238000011109 contamination Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
- 201000011510 cancer Diseases 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 108090000672 Annexin A5 Proteins 0.000 description 6
- 102000004121 Annexin A5 Human genes 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000003556 assay Methods 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 230000037396 body weight Effects 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000012981 Hank's balanced salt solution Substances 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 239000003638 chemical reducing agent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 108010033040 Histones Proteins 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 241000204031 Mycoplasma Species 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- KVXMLLMZXPRPNG-VOTSOKGWSA-N methyl (e)-3-(4-formylphenyl)prop-2-enoate Chemical compound COC(=O)\C=C\C1=CC=C(C=O)C=C1 KVXMLLMZXPRPNG-VOTSOKGWSA-N 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- 230000003612 virological effect Effects 0.000 description 4
- LBOUHDMYVURTMA-AATRIKPKSA-N (e)-3-(4-formylphenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=C(C=O)C=C1 LBOUHDMYVURTMA-AATRIKPKSA-N 0.000 description 3
- PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 3
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 102000006947 Histones Human genes 0.000 description 3
- 206010027476 Metastases Diseases 0.000 description 3
- 229930189037 Trapoxin Natural products 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000010261 cell growth Effects 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 208000029742 colonic neoplasm Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 208000020816 lung neoplasm Diseases 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 235000018102 proteins Nutrition 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 108010060597 trapoxin A Proteins 0.000 description 3
- RTKIYFITIVXBLE-QEQCGCAPSA-N trichostatin A Chemical compound ONC(=O)/C=C/C(/C)=C/[C@@H](C)C(=O)C1=CC=C(N(C)C)C=C1 RTKIYFITIVXBLE-QEQCGCAPSA-N 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- DUCBSHDQTBWWLC-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl-(1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonyl)amino]-n-hydroxypropanamide Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)N(C(C)C(=O)NO)CC1=CC=CC=C1Cl DUCBSHDQTBWWLC-UHFFFAOYSA-N 0.000 description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 2
- 208000026310 Breast neoplasm Diseases 0.000 description 2
- 229940122964 Deacetylase inhibitor Drugs 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- 206010016654 Fibrosis Diseases 0.000 description 2
- 230000037057 G1 phase arrest Effects 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- RTKIYFITIVXBLE-UHFFFAOYSA-N Trichostatin A Natural products ONC(=O)C=CC(C)=CC(C)C(=O)C1=CC=C(N(C)C)C=C1 RTKIYFITIVXBLE-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 230000006229 amino acid addition Effects 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000004663 cell proliferation Effects 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000008355 dextrose injection Substances 0.000 description 2
- 230000004069 differentiation Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000004761 fibrosis Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 208000014829 head and neck neoplasm Diseases 0.000 description 2
- 238000002513 implantation Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- 208000032839 leukemia Diseases 0.000 description 2
- 238000012417 linear regression Methods 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 208000037841 lung tumor Diseases 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000009401 metastasis Effects 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- KVXMLLMZXPRPNG-UHFFFAOYSA-N methyl 3-(4-formylphenyl)prop-2-enoate Chemical compound COC(=O)C=CC1=CC=C(C=O)C=C1 KVXMLLMZXPRPNG-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229940026778 other chemotherapeutics in atc Drugs 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- 230000000644 propagated effect Effects 0.000 description 2
- XJMOSONTPMZWPB-UHFFFAOYSA-M propidium iodide Chemical compound [I-].[I-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CCC[N+](C)(CC)CC)=C1C1=CC=CC=C1 XJMOSONTPMZWPB-UHFFFAOYSA-M 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- 208000023958 prostate neoplasm Diseases 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000006268 reductive amination reaction Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000008054 sulfonate salts Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- GLUABPSZMHYCNO-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydropyrrolo[3,2-b]pyrrole Chemical compound N1CCC2NCCC21 GLUABPSZMHYCNO-UHFFFAOYSA-N 0.000 description 1
- PIHAUZGWAXLKCA-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydro-1,8-naphthyridine Chemical compound N1CCCC2CCCNC21 PIHAUZGWAXLKCA-UHFFFAOYSA-N 0.000 description 1
- QOBTUJBWKJKGCI-UHFFFAOYSA-N 1,2,3,4,6,11-hexahydropyrido[3,2-c][1,5]benzodiazepin-5-one Chemical compound O=C1NC2=CC=CC=C2NC2=C1CCCN2 QOBTUJBWKJKGCI-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 description 1
- JQBOAIAQGAIKBN-UHFFFAOYSA-N 1,5-dihydropyrido[2,3-b][1,4]diazepin-4-one Chemical compound N1C=CC(=O)NC2=NC=CC=C21 JQBOAIAQGAIKBN-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
- HIYWOHBEPVGIQN-UHFFFAOYSA-N 1h-benzo[g]indole Chemical compound C1=CC=CC2=C(NC=C3)C3=CC=C21 HIYWOHBEPVGIQN-UHFFFAOYSA-N 0.000 description 1
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 description 1
- IHKOXYNAMXNNDK-UHFFFAOYSA-N 2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan Chemical compound C1COC2OCCC21 IHKOXYNAMXNNDK-UHFFFAOYSA-N 0.000 description 1
- HCJXTKKLAOJVHJ-UHFFFAOYSA-N 2,3,3a,4a,5,6,7,7a,8,8a-decahydro-1h-dicyclopenta[2,1-b:2',1'-f]pyran Chemical compound C1C2CCCC2OC2CCCC21 HCJXTKKLAOJVHJ-UHFFFAOYSA-N 0.000 description 1
- URDIRPDCQWYRTI-UHFFFAOYSA-N 2,3,3a,5,6,6a-hexahydrothieno[3,2-b]thiophene Chemical compound S1CCC2SCCC21 URDIRPDCQWYRTI-UHFFFAOYSA-N 0.000 description 1
- GBCQLGDTLMHVHU-UHFFFAOYSA-N 2,3,4,4a,5,6,7,8,9,9a-decahydro-1h-benzo[7]annulene Chemical compound C1CCCCC2CCCCC21 GBCQLGDTLMHVHU-UHFFFAOYSA-N 0.000 description 1
- CPVSLHQIPGTMLH-UHFFFAOYSA-N 2-(2-methyl-1h-indol-3-yl)ethanamine Chemical compound C1=CC=C2C(CCN)=C(C)NC2=C1 CPVSLHQIPGTMLH-UHFFFAOYSA-N 0.000 description 1
- XARVANDLQOZMMJ-CHHVJCJISA-N 2-[(z)-[1-(2-amino-1,3-thiazol-4-yl)-2-oxo-2-(2-oxoethylamino)ethylidene]amino]oxy-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)O\N=C(/C(=O)NCC=O)C1=CSC(N)=N1 XARVANDLQOZMMJ-CHHVJCJISA-N 0.000 description 1
- SOBMVBSSEJZEBX-UHFFFAOYSA-N 2-[2,2-bis(2-octadecanoyloxyethoxymethyl)butoxy]ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCOCC(CC)(COCCOC(=O)CCCCCCCCCCCCCCCCC)COCCOC(=O)CCCCCCCCCCCCCCCCC SOBMVBSSEJZEBX-UHFFFAOYSA-N 0.000 description 1
- JBKINHFZTVLNEM-UHFFFAOYSA-N 2-bromoethoxy-tert-butyl-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OCCBr JBKINHFZTVLNEM-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- LYUQWQRTDLVQGA-UHFFFAOYSA-N 3-phenylpropylamine Chemical compound NCCCC1=CC=CC=C1 LYUQWQRTDLVQGA-UHFFFAOYSA-N 0.000 description 1
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 1
- OMGNOSZSCQGCGV-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1,4]benzodiazepine Chemical compound C1NC2=CC=CC=C2NC2=CC=CC=C12 OMGNOSZSCQGCGV-UHFFFAOYSA-N 0.000 description 1
- CCKWMCUOHJAVOL-UHFFFAOYSA-N 7-hydroxy-4-(trifluoromethyl)chromen-2-one Chemical compound FC(F)(F)C1=CC(=O)OC2=CC(O)=CC=C21 CCKWMCUOHJAVOL-UHFFFAOYSA-N 0.000 description 1
- ZIUYHTQZEPDUCZ-UHFFFAOYSA-N 7h-pyrrolo[2,3-h]quinoline Chemical compound C1=CN=C2C(C=CN3)=C3C=CC2=C1 ZIUYHTQZEPDUCZ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 108010039627 Aprotinin Proteins 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 206010005003 Bladder cancer Diseases 0.000 description 1
- 208000003174 Brain Neoplasms Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 208000002699 Digestive System Neoplasms Diseases 0.000 description 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 206010017993 Gastrointestinal neoplasms Diseases 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 108010043121 Green Fluorescent Proteins Proteins 0.000 description 1
- 101001067880 Homo sapiens Histone H4 Proteins 0.000 description 1
- 238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 208000008839 Kidney Neoplasms Diseases 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- GDBQQVLCIARPGH-UHFFFAOYSA-N Leupeptin Natural products CC(C)CC(NC(C)=O)C(=O)NC(CC(C)C)C(=O)NC(C=O)CCCN=C(N)N GDBQQVLCIARPGH-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 125000001429 N-terminal alpha-amino-acid group Chemical group 0.000 description 1
- 206010029260 Neuroblastoma Diseases 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 208000031481 Pathologic Constriction Diseases 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 239000012614 Q-Sepharose Substances 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 206010038389 Renal cancer Diseases 0.000 description 1
- 201000000582 Retinoblastoma Diseases 0.000 description 1
- 239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000006859 Swern oxidation reaction Methods 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 108091023040 Transcription factor Proteins 0.000 description 1
- 102000040945 Transcription factor Human genes 0.000 description 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
- 208000008385 Urogenital Neoplasms Diseases 0.000 description 1
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000004947 alkyl aryl amino group Chemical group 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000033115 angiogenesis Effects 0.000 description 1
- 238000002399 angioplasty Methods 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229960004405 aprotinin Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 230000003833 cell viability Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 230000036755 cellular response Effects 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- PJQCANLCUDUPRF-UHFFFAOYSA-N dibenzocycloheptene Chemical compound C1CC2=CC=CC=C2CC2=CC=CC=C12 PJQCANLCUDUPRF-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000007877 drug screening Methods 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 1
- BVSRWCMAJISCTD-UHFFFAOYSA-N ethyl 2-diethoxyphosphorylpropanoate Chemical compound CCOC(=O)C(C)P(=O)(OCC)OCC BVSRWCMAJISCTD-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000000799 fluorescence microscopy Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- YRTCKZIKGWZNCU-UHFFFAOYSA-N furo[3,2-b]pyridine Chemical compound C1=CC=C2OC=CC2=N1 YRTCKZIKGWZNCU-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 1
- 230000006195 histone acetylation Effects 0.000 description 1
- BNRNAKTVFSZAFA-UHFFFAOYSA-N hydrindane Chemical compound C1CCCC2CCCC21 BNRNAKTVFSZAFA-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 206010020718 hyperplasia Diseases 0.000 description 1
- 230000003463 hyperproliferative effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- ZPNFWUPYTFPOJU-LPYSRVMUSA-N iniprol Chemical compound C([C@H]1C(=O)NCC(=O)NCC(=O)N[C@H]2CSSC[C@H]3C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(N[C@H](C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC=4C=CC=CC=4)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=4C=CC=CC=4)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC2=O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]2N(CCC2)C(=O)[C@@H](N)CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N2[C@@H](CCC2)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N2[C@@H](CCC2)C(=O)N3)C(=O)NCC(=O)NCC(=O)N[C@@H](C)C(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@H](C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H](C(=O)N1)C(C)C)[C@@H](C)O)[C@@H](C)CC)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 ZPNFWUPYTFPOJU-LPYSRVMUSA-N 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 239000013038 irreversible inhibitor Substances 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 201000010982 kidney cancer Diseases 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- GDBQQVLCIARPGH-ULQDDVLXSA-N leupeptin Chemical compound CC(C)C[C@H](NC(C)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C=O)CCCN=C(N)N GDBQQVLCIARPGH-ULQDDVLXSA-N 0.000 description 1
- 108010052968 leupeptin Proteins 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 201000005296 lung carcinoma Diseases 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 208000026037 malignant tumor of neck Diseases 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- RFKMCNOHBTXSMU-UHFFFAOYSA-N methoxyflurane Chemical compound COC(F)(F)C(Cl)Cl RFKMCNOHBTXSMU-UHFFFAOYSA-N 0.000 description 1
- 229960002455 methoxyflurane Drugs 0.000 description 1
- RPLQUEPXYREGMA-VAWYXSNFSA-N methyl (e)-3-[4-[[2-(2-methyl-1h-indol-3-yl)ethylamino]methyl]phenyl]prop-2-enoate Chemical compound C1=CC(/C=C/C(=O)OC)=CC=C1CNCCC1=C(C)NC2=CC=CC=C12 RPLQUEPXYREGMA-VAWYXSNFSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000036457 multidrug resistance Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- LOYIGNDQOZNJNZ-UHFFFAOYSA-N n-hydroxy-2-[(4-methoxyphenyl)sulfonyl-[(4-nitrophenyl)methyl]amino]acetamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(CC(=O)NO)CC1=CC=C([N+]([O-])=O)C=C1 LOYIGNDQOZNJNZ-UHFFFAOYSA-N 0.000 description 1
- 230000017095 negative regulation of cell growth Effects 0.000 description 1
- 208000025440 neoplasm of neck Diseases 0.000 description 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 description 1
- NZFHJBSDSXDUAO-UHFFFAOYSA-N o-tritylhydroxylamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(ON)C1=CC=CC=C1 NZFHJBSDSXDUAO-UHFFFAOYSA-N 0.000 description 1
- 208000023983 oral cavity neoplasm Diseases 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 230000029279 positive regulation of transcription, DNA-dependent Effects 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 201000002793 renal fibrosis Diseases 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000013037 reversible inhibitor Substances 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
- 238000013207 serial dilution Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- VPZRWNZGLKXFOE-UHFFFAOYSA-M sodium phenylbutyrate Chemical compound [Na+].[O-]C(=O)CCCC1=CC=CC=C1 VPZRWNZGLKXFOE-UHFFFAOYSA-M 0.000 description 1
- 229960002232 sodium phenylbutyrate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000036262 stenosis Effects 0.000 description 1
- 208000037804 stenosis Diseases 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 229930185603 trichostatin Natural products 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
- C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
- C04B35/632—Organic additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
-
- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Ceramic Engineering (AREA)
- Health & Medical Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Veterinary Medicine (AREA)
- Structural Engineering (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Materials Engineering (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22994300P | 2000-09-01 | 2000-09-01 | |
| US29223201P | 2001-05-18 | 2001-05-18 | |
| PCT/EP2001/010037 WO2002022577A2 (en) | 2000-09-01 | 2001-08-30 | Hydroxamate derivatives useful as deacetylase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ524365A true NZ524365A (en) | 2004-11-26 |
Family
ID=26923760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ524365A NZ524365A (en) | 2000-09-01 | 2001-08-30 | Hydroxamate derivatives useful as deacetylase inhibitors |
Country Status (35)
| Country | Link |
|---|---|
| US (5) | US6552065B2 (Direct) |
| EP (2) | EP1870399A1 (Direct) |
| JP (1) | JP4012819B2 (Direct) |
| KR (1) | KR100585484B1 (Direct) |
| CN (1) | CN1300110C (Direct) |
| AR (1) | AR035057A1 (Direct) |
| AT (1) | ATE376999T1 (Direct) |
| AU (2) | AU2001282129B2 (Direct) |
| BE (1) | BE2015C062I2 (Direct) |
| BR (1) | BRPI0113669B8 (Direct) |
| CA (1) | CA2420899C (Direct) |
| CY (2) | CY1107839T1 (Direct) |
| CZ (1) | CZ302707B6 (Direct) |
| DE (1) | DE60131179T2 (Direct) |
| DK (1) | DK1318980T3 (Direct) |
| EC (1) | ECSP034492A (Direct) |
| ES (1) | ES2292610T3 (Direct) |
| FR (1) | FR15C0086I2 (Direct) |
| HU (2) | HU229796B1 (Direct) |
| IL (2) | IL154574A0 (Direct) |
| LU (1) | LU92890I2 (Direct) |
| MX (1) | MXPA03001832A (Direct) |
| MY (1) | MY136892A (Direct) |
| NL (1) | NL300778I2 (Direct) |
| NO (2) | NO324942B1 (Direct) |
| NZ (1) | NZ524365A (Direct) |
| PE (1) | PE20020354A1 (Direct) |
| PL (1) | PL221738B1 (Direct) |
| PT (1) | PT1318980E (Direct) |
| RU (1) | RU2302408C3 (Direct) |
| SI (1) | SI1318980T1 (Direct) |
| SK (1) | SK287609B6 (Direct) |
| TW (1) | TWI286544B (Direct) |
| WO (1) | WO2002022577A2 (Direct) |
| ZA (1) | ZA200301423B (Direct) |
Families Citing this family (460)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6777217B1 (en) | 1996-03-26 | 2004-08-17 | President And Fellows Of Harvard College | Histone deacetylases, and uses related thereto |
| US6822267B1 (en) * | 1997-08-20 | 2004-11-23 | Advantest Corporation | Signal transmission circuit, CMOS semiconductor device, and circuit board |
| EP1233958B1 (en) | 1999-11-23 | 2011-06-29 | MethylGene Inc. | Inhibitors of histone deacetylase |
| US20030129724A1 (en) | 2000-03-03 | 2003-07-10 | Grozinger Christina M. | Class II human histone deacetylases, and uses related thereto |
| PE20020354A1 (es) | 2000-09-01 | 2002-06-12 | Novartis Ag | Compuestos de hidroxamato como inhibidores de histona-desacetilasa (hda) |
| DE60115279T2 (de) | 2000-09-29 | 2006-12-28 | Topotarget Uk Ltd., Abingdon | Carbaminsäurederivate enthaltend eine amidgruppe als hdac-inhibitoren |
| US7312247B2 (en) * | 2001-03-27 | 2007-12-25 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors |
| CA2463552C (en) * | 2001-10-16 | 2011-05-17 | Sloan-Kettering Institute For Cancer Research | Treatment of neurodegenerative diseases and cancer of the brain |
| US7402603B2 (en) * | 2001-11-06 | 2008-07-22 | Novartis Ag | Cyclooxygenase-2 inhibitor/histone deacetylase inhibitor combination |
| US7148257B2 (en) | 2002-03-04 | 2006-12-12 | Merck Hdac Research, Llc | Methods of treating mesothelioma with suberoylanilide hydroxamic acid |
| IL163909A0 (en) | 2002-03-04 | 2005-12-18 | Aton Pharma Inc | Methods of inducing terminal differentiation |
| US7456219B2 (en) | 2002-03-04 | 2008-11-25 | Merck Hdac Research, Llc | Polymorphs of suberoylanilide hydroxamic acid |
| US7629343B2 (en) | 2002-04-03 | 2009-12-08 | Topotarget Uk Limited | Carbamic acid compounds comprising a piperazine linkage as HDAC inhibitors |
| US7495022B2 (en) | 2002-04-11 | 2009-02-24 | Sk Chemicals Co., Ltd. | α,β-unsaturated hydroxamic acid derivatives and their use as histone deacetylase inhibitors |
| US20040018968A1 (en) * | 2002-04-15 | 2004-01-29 | George Sgouros | Use of histone deacetylase inhibitors in combination with radiation for the treatment of cancer |
| ATE476995T1 (de) * | 2002-06-10 | 2010-08-15 | Novartis Pharma Gmbh | Epothilone enthaltende kombinationen und deren pharmazeutische verwendungen |
| JP4804004B2 (ja) * | 2002-08-20 | 2011-10-26 | アステラス製薬株式会社 | 関節軟骨細胞外マトリクス分解阻害剤 |
| CA2498210C (en) * | 2002-09-13 | 2011-10-18 | Virginia Commonwealth University | Combination of a) n-{5-[4-(4-methyl-piperazino-methyl)-benzoylamido]-2-methylphenyl}-4-(3-pyridyl)-2-pyrimidine-amine and b) a histone deacetylase inhibitor for the treatment of leukemia |
| US7154002B1 (en) | 2002-10-08 | 2006-12-26 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| US7250514B1 (en) | 2002-10-21 | 2007-07-31 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| WO2004046107A1 (en) * | 2002-11-19 | 2004-06-03 | Takeda Pharmaceutical Company Limited | Indole derivatives as somatostatin agonists or antagonists |
| WO2004052292A2 (en) | 2002-12-06 | 2004-06-24 | University Of South Florida | Histone deacetylase inhibitor enhancement of trail-induced apoptosis |
| US7135493B2 (en) | 2003-01-13 | 2006-11-14 | Astellas Pharma Inc. | HDAC inhibitor |
| CA2513246A1 (en) | 2003-01-17 | 2004-08-05 | Topotarget Uk Limited | Carbamic acid compounds comprising an ester or ketone linkage as hdac inhibitors |
| AU2003900587A0 (en) * | 2003-02-11 | 2003-02-27 | Fujisawa Pharmaceutical Co., Ltd. | Hdac inhibitor |
| AU2003900608A0 (en) * | 2003-02-11 | 2003-02-27 | Fujisawa Pharmaceutical Co., Ltd. | Hdac inhibitor |
| AU2004215624B2 (en) | 2003-02-25 | 2011-06-02 | Topotarget Uk Limited | Hydroxamic acid compounds comprising a bicyclic heteroaryl group as HDAC inhibitors |
| KR20050122210A (ko) | 2003-03-17 | 2005-12-28 | 다케다 샌디에고, 인코포레이티드 | 히스톤 탈아세틸화 효소 억제제 |
| WO2004103358A2 (en) * | 2003-05-21 | 2004-12-02 | Novartis Ag | Combination of histone deacetylase inhibitors with chemotherapeutic agents |
| WO2005011598A2 (en) | 2003-07-31 | 2005-02-10 | University Of South Florida | Leukemia treatment method and composition |
| JP2007501775A (ja) * | 2003-08-07 | 2007-02-01 | ノバルティス アクチエンゲゼルシャフト | 免疫抑制剤としてのヒストンデアセチラーゼ阻害剤 |
| AU2004262927B2 (en) | 2003-08-08 | 2008-05-22 | Novartis Ag | Combinations comprising staurosporines |
| ATE462426T1 (de) | 2003-08-26 | 2010-04-15 | Merck Hdac Res Llc | Verwendung von saha zur behandlung von mesotheliom |
| JP2007504131A (ja) | 2003-08-29 | 2007-03-01 | エートン ファーマ インコーポレーティッド | 癌の組み合わせ処置法 |
| CN100455564C (zh) * | 2003-09-12 | 2009-01-28 | 深圳微芯生物科技有限责任公司 | 组蛋白去乙酰化酶抑制剂及其药用制剂的制备和应用 |
| AU2004271730A1 (en) * | 2003-09-18 | 2005-03-24 | Novartis Ag | Combination of a histone deacetylase inhibitor with a death receptor ligand |
| SI1673349T1 (sl) * | 2003-09-22 | 2010-10-29 | S Bio Pte Ltd | Derivati benzimidazola: priprava in farmacevtske uporabe |
| BRPI0414581C1 (pt) | 2003-09-22 | 2021-05-25 | Mei Pharma Inc | composto, composição farmacêutica compreendendo o referido composto e uso do referido composto |
| KR20060097000A (ko) * | 2003-09-23 | 2006-09-13 | 노파르티스 아게 | 화학요법제와 ｖｅｇｆ 수용체 저해제의 배합물 |
| US20070167499A1 (en) * | 2003-10-27 | 2007-07-19 | A*Bio Pte Ltd. | Biaryl linked hydroxamates: preparation and pharmaceutical applications |
| AU2004296764B2 (en) * | 2003-12-02 | 2011-04-28 | The Ohio State University Research Foundation | Zn2+ -chelating motif-tethered short -chain fatty acids as a novel class of histone deacetylase inhibitors |
| EP1541549A1 (en) | 2003-12-12 | 2005-06-15 | Exonhit Therapeutics S.A. | Tricyclic hydroxamate and benzaminde derivatives, compositions and methods |
| WO2005066151A2 (en) * | 2003-12-19 | 2005-07-21 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| WO2005065681A1 (en) * | 2003-12-19 | 2005-07-21 | Takeda San Diego, Inc. | N- hydroxy-3-(3-(1h-imidazol-2-yl)-phenyl)-acrylamide derivatives and related compounds as histone deacetylase (hdac) inhibitors for the treatment of cancer |
| US20050197336A1 (en) * | 2004-03-08 | 2005-09-08 | Miikana Therapeutics Corporation | Inhibitors of histone deacetylase |
| US7345043B2 (en) * | 2004-04-01 | 2008-03-18 | Miikana Therapeutics | Inhibitors of histone deacetylase |
| TWI417092B (zh) | 2004-04-07 | 2013-12-01 | Novartis Ag | Ｉａｐ抑制劑 |
| US7507858B2 (en) * | 2004-07-19 | 2009-03-24 | Merck & Co., Inc. | Histone deacetylase inhibitors |
| CA2576667A1 (en) * | 2004-08-09 | 2006-02-16 | Astellas Pharma Inc. | Hydroxyamide compounds having activity as inhibitors of histone deacetylase (hdac) |
| ITMI20041869A1 (it) * | 2004-10-01 | 2005-01-01 | Dac Srl | Nuovi inibitori delle istone deacetilasi |
| US8242175B2 (en) | 2004-10-01 | 2012-08-14 | Dac S.R.L. | Class of histone deacetylase inhibitors |
| US20070021612A1 (en) * | 2004-11-04 | 2007-01-25 | University Of Notre Dame Du Lac | Processes and compounds for preparing histone deacetylase inhibitors and intermediates thereof |
| US7235688B1 (en) | 2004-11-04 | 2007-06-26 | University Of Notre Dame Du Lac | Process for preparing histone deacetylase inhibitors and intermediates thereof |
| US7642275B2 (en) | 2004-12-16 | 2010-01-05 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| AU2006214319A1 (en) | 2005-02-14 | 2006-08-24 | Miikana Therapeutics, Inc. | Fused heterocyclic compounds useful as inhibitors of histone deacetylase |
| US7666880B2 (en) | 2005-03-21 | 2010-02-23 | S*Bio Pte Ltd. | Imidazo[1,2-A]pyridine derivatives: preparation and pharmaceutical applications |
| AU2006226861B2 (en) | 2005-03-22 | 2012-08-16 | Dana-Farber Cancer Institute, Inc. | Treatment of protein degradation disorders |
| GB0509223D0 (en) * | 2005-05-05 | 2005-06-15 | Chroma Therapeutics Ltd | Enzyme inhibitors |
| GB0509225D0 (en) | 2005-05-05 | 2005-06-15 | Chroma Therapeutics Ltd | Inhibitors of enzymatic activity |
| EP1896436A2 (en) | 2005-05-11 | 2008-03-12 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| TWI365068B (en) | 2005-05-20 | 2012-06-01 | Merck Sharp & Dohme | Formulations of suberoylanilide hydroxamic acid and methods for producing same |
| GB0510390D0 (en) | 2005-05-20 | 2005-06-29 | Novartis Ag | Organic compounds |
| EA200800321A1 (ru) | 2005-07-14 | 2008-06-30 | Такеда Сан Диего, Инк. | Ингибиторы гистондеацетилазы |
| WO2007016532A2 (en) * | 2005-08-02 | 2007-02-08 | Novartis Ag | Mutations and polymorphisms of hdac4 |
| KR101354237B1 (ko) | 2005-08-03 | 2014-01-22 | 노파르티스 아게 | 골수종 치료를 위한 ｈｄａｃ 저해제의 용도 |
| EP1915141A1 (en) * | 2005-08-10 | 2008-04-30 | Novartis AG | Method of use of deacetylase inhibitors |
| KR20080044277A (ko) * | 2005-08-11 | 2008-05-20 | 노파르티스 아게 | 유기 화합물의 조합물 |
| EP2258357A3 (en) | 2005-08-26 | 2011-04-06 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| KR20080052611A (ko) * | 2005-08-26 | 2008-06-11 | 메틸진 인크. | 히스톤 탈아세틸 효소의 벤조디아제핀 및 벤조피페라진유도체 억제제 |
| WO2007025177A2 (en) | 2005-08-26 | 2007-03-01 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| WO2007030455A2 (en) * | 2005-09-07 | 2007-03-15 | Novartis Ag | Mutations and polymorphisms of hdac10 |
| WO2007030454A2 (en) * | 2005-09-07 | 2007-03-15 | Novartis Ag | Mutations and polymorphisms of hdac9 |
| WO2007038073A2 (en) * | 2005-09-22 | 2007-04-05 | Novartis Ag | Mutations and polymorphisms of hdac11 |
| WO2007038459A2 (en) | 2005-09-27 | 2007-04-05 | Novartis Ag | Carboxyamine compounds and their use in the treatment of hdac dependent diseases |
| WO2007047998A2 (en) * | 2005-10-21 | 2007-04-26 | Novartis Ag | Mutations and polymorphisms of hdac2 |
| JP2009512711A (ja) | 2005-10-21 | 2009-03-26 | ブレインセルス，インコーポレイティド | Ｐｄｅ阻害による神経新生の調節 |
| JP2009512732A (ja) * | 2005-10-24 | 2009-03-26 | ノバルティス アクチエンゲゼルシャフト | ヒストンデアセチラーゼ阻害剤および照射の組合せ |
| EP1942879A1 (en) | 2005-10-31 | 2008-07-16 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| WO2007053502A2 (en) * | 2005-11-01 | 2007-05-10 | Novartis Ag | Mutations and polymorphisms of hdac5 |
| WO2007058992A2 (en) * | 2005-11-14 | 2007-05-24 | Novartis Ag | Mutations and polymorphisms of hdac6 |
| NZ568182A (en) | 2005-11-21 | 2010-08-27 | Novartis Ag | Neuroendocrine tumor treatment using MTOR inhibitors |
| US20070207950A1 (en) * | 2005-12-21 | 2007-09-06 | Duke University | Methods and compositions for regulating HDAC6 activity |
| WO2007084390A2 (en) * | 2006-01-13 | 2007-07-26 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| PT1981877E (pt) * | 2006-02-07 | 2012-05-24 | Astellas Pharma Inc | Compostos de n-hidroxiacrilamida |
| US8222423B2 (en) * | 2006-02-14 | 2012-07-17 | Dana-Farber Cancer Institute, Inc. | Bifunctional histone deacetylase inhibitors |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| GB0605120D0 (en) | 2006-03-14 | 2006-04-26 | Novartis Ag | Organic Compounds |
| CN102671196B (zh) | 2006-04-05 | 2014-12-03 | 诺华股份有限公司 | 用于治疗癌症的治疗剂的组合 |
| KR20080109068A (ko) | 2006-04-05 | 2008-12-16 | 노파르티스 아게 | 암을 치료하기 위한 ｂｃｒ-ａｂｌ/ｃ-ｋｉｔ/ｐｄｇｆ-ｒ ｔｋ 억제제를 포함하는 조합물 |
| EP2447359B1 (en) | 2006-04-14 | 2015-11-04 | Cell Signaling Technology, Inc. | Gene defects and mutant ALK kinase in human solid tumors |
| US8168383B2 (en) | 2006-04-14 | 2012-05-01 | Cell Signaling Technology, Inc. | Gene defects and mutant ALK kinase in human solid tumors |
| CA2649877A1 (en) | 2006-04-24 | 2007-12-21 | Gloucester Pharmaceuticals | Gemcitabine combination therapy |
| US20090018142A9 (en) * | 2006-05-02 | 2009-01-15 | Zhengping Zhuang | Use of phosphatases to treat tumors overexpressing N-CoR |
| EP2272511A1 (en) | 2006-05-09 | 2011-01-12 | Novartis AG | Combination comprising an iron chelator and an anti-neoplastic agent and use thereof |
| CA2651862A1 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | 5 ht receptor mediated neurogenesis |
| EP2382975A3 (en) | 2006-05-09 | 2012-02-29 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| WO2007146730A2 (en) | 2006-06-08 | 2007-12-21 | Gloucester Pharmaceuticals | Deacetylase inhibitor therapy |
| WO2007146716A2 (en) | 2006-06-12 | 2007-12-21 | Novartis Ag | Polymorphs of n-hydroxy-3-[4-[[[2-(2-methyl-1h-indol-3-yl)ethyl]amino]methyl]phenyl]-2e-2-propenamide |
| EP2032531B1 (en) * | 2006-06-12 | 2016-02-10 | Novartis AG | Salts of n-hydroxy-3-[4-[[[2-(2-methyl-1h-indol-3-yl)ethyl]amino]methyl]phenyl]-2e-2-propenamide |
| AU2007257882B2 (en) | 2006-06-12 | 2011-09-08 | Secura Bio Inc. | Process for making salts of N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide |
| CN101466672B (zh) * | 2006-06-12 | 2012-05-16 | 诺瓦提斯公司 | N-羟基-3-[4-[[[2-(2-甲基-1h-吲哚-3-基)乙基]氨基]甲基]苯基]-2e-2-丙烯酰胺的盐 |
| KR101540194B1 (ko) * | 2006-06-12 | 2015-07-28 | 노파르티스 아게 | Ｎ-히드록시-3-［4-［［［2-(2-메틸-1ｈ-인돌-3-일)에틸］아미노］메틸］페닐］-2ｅ-2-프로펜아미드 및 이의 출발 물질의 제조 방법 |
| US20100008923A1 (en) * | 2006-06-26 | 2010-01-14 | Novartis Ag | Organic Compounds |
| US7998971B2 (en) | 2006-09-08 | 2011-08-16 | Braincells Inc. | Combinations containing a 4-acylaminopyridine derivative |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| EP2064211B1 (en) | 2006-09-20 | 2015-11-11 | MEI Pharma, Inc. | Imidazo[1,2-a]pyridine hydroxymate compounds that are inhibitors of histone deacetylase |
| CA2663614A1 (en) * | 2006-09-28 | 2008-04-10 | Merck And Co., Inc. | Amine base salts of saha and polymorphs thereof |
| DE602007013441D1 (de) | 2006-09-29 | 2011-05-05 | Novartis Ag | Pyrazolopyrimidine als pi3k-lipidkinasehemmer |
| GB0619753D0 (en) * | 2006-10-06 | 2006-11-15 | Chroma Therapeutics Ltd | Enzyme inhibitors |
| ES2509342T3 (es) | 2006-10-30 | 2014-10-17 | Chroma Therapeutics Limited | Hidroxamatos como inhibidores de histona desacetilasa |
| CN101677977A (zh) * | 2006-11-10 | 2010-03-24 | 欣达克斯制药公司 | 用于治疗癌症的ERα+配体和组蛋白脱乙酰化酶抑制剂组合 |
| PL2099451T3 (pl) * | 2006-12-04 | 2016-07-29 | Novartis Ag | Kombinacja inhibitora HDAC oraz antymetabolitu |
| EP2099756A1 (en) * | 2006-12-15 | 2009-09-16 | Astellas Pharma Inc. | N-hydroxyacrylamide compounds |
| MX2009007343A (es) * | 2007-01-10 | 2009-07-15 | Novartis Ag | Formulaciones de inhibidores de desacetilasa. |
| CN103788108B (zh) | 2007-02-06 | 2017-04-12 | 利克斯特生物技术公司 | 氧杂双环庚烷和氧杂双环庚烯，它们的制备及用途 |
| JP2010519209A (ja) | 2007-02-15 | 2010-06-03 | ノバルティス アーゲー | 癌を処置するためのｌｂｈ５８９と他の治療剤の組み合わせ剤 |
| CA2680838A1 (en) | 2007-03-28 | 2008-10-16 | Santen Pharmaceutical Co., Ltd. | Intraocular pressure-lowering agent comprising compound having histone deacetylase inhibitory effect as active ingredient |
| WO2008122115A1 (en) | 2007-04-09 | 2008-10-16 | Methylgene Inc. | Inhibitors of histone deacetylase |
| CL2008001269A1 (es) * | 2007-05-04 | 2008-12-19 | Novartis Ag | Uso de un inhibidor de desacetilasa de histona par el tratamiento de canceres gastro intestinales |
| AU2008251499A1 (en) * | 2007-05-11 | 2008-11-20 | Novartis Ag | Use of HDAC inhibitors for the treatment of melanoma |
| WO2008150782A1 (en) * | 2007-05-30 | 2008-12-11 | Novartis Ag | Use of hdac inhibitors for the treatment of bone destruction |
| US7737175B2 (en) | 2007-06-01 | 2010-06-15 | Duke University | Methods and compositions for regulating HDAC4 activity |
| AU2008284364A1 (en) * | 2007-08-03 | 2009-02-12 | Lixte Biotechnology, Inc. | Use of phosphatases to treat neuroblastomas and medulloblastomas |
| CL2008002786A1 (es) * | 2007-09-20 | 2009-05-15 | Novartis Ag | Torta farmceuticamente aceptable, formada por liofilizacion, que comprende: n-hidroxi-3-[4-[[[2-(2-metil-1h-indol-3-il]-etil]-amino]-metil]-fenil]-2e-2-propenamida o una sal, un regulador de ph seleciondo de lactato o acidop lactico, fodfato o acido fosforico o una combinacion y un agente de volumen; proceso de elaboracion. |
| EP2200439B1 (en) | 2007-10-01 | 2017-03-22 | Lixte Biotechnology, Inc. | Hdac inhibitors |
| US8450525B2 (en) * | 2007-10-22 | 2013-05-28 | Orchid Chemicals & Pharmaceuticals Limited | Histone deacetylase inhibitors |
| CN101417967A (zh) * | 2007-10-26 | 2009-04-29 | 浙江海正药业股份有限公司 | 组蛋白去乙酰酶抑制剂、其组合物及其应用 |
| US20090131367A1 (en) * | 2007-11-19 | 2009-05-21 | The Regents Of The University Of Colorado | Combinations of HDAC Inhibitors and Proteasome Inhibitors |
| CA2706750A1 (en) * | 2007-11-27 | 2009-06-04 | Ottawa Health Research Institute | Amplification of cancer-specific oncolytic viral infection by histone deacetylase inhibitors |
| CA2708281A1 (en) | 2007-12-11 | 2009-08-27 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitors using metal binding moieties in combination with targeting moieties |
| ITFI20070288A1 (it) | 2007-12-21 | 2009-06-22 | A I L Firenze Sezione Autonoma | Inibitori delle deacetilasi istoniche |
| EP2100879A1 (en) * | 2008-03-13 | 2009-09-16 | 4Sc Ag | Novel N-substituted tetrahydroisoquinoline/isoindoline hydroxamic acid compounds |
| KR101673621B1 (ko) | 2008-03-24 | 2016-11-07 | 노파르티스 아게 | 아릴술폰아미드-계 매트릭스 메탈로프로테아제 억제제 |
| JP5330498B2 (ja) | 2008-03-26 | 2013-10-30 | ノバルティス アーゲー | 脱アセチル化酵素ｂのヒドロキサメートを基にした阻害剤 |
| AU2009270886A1 (en) * | 2008-07-18 | 2010-01-21 | Novartis Ag | Use of HDAC inhibitors for the treatment of Hodgkin's disease |
| AU2009274549B2 (en) | 2008-07-23 | 2014-05-01 | Dana-Farber Cancer Institute, Inc. | Deacetylase inhibitors and uses thereof |
| US8227473B2 (en) | 2008-08-01 | 2012-07-24 | Lixte Biotechnology, Inc. | Oxabicycloheptanes and oxabicycloheptenes, their preparation and use |
| CA2730148C (en) * | 2008-08-01 | 2018-04-03 | Lixte Biotechnology, Inc. | Neuroprotective agents for the prevention and treatment of neurodegenerative diseases |
| CA2730428A1 (en) * | 2008-08-01 | 2010-02-04 | Lixte Biotechnology, Inc. | Methods for regulating cell mitosis by inhibiting serine/threonine phosphatase |
| WO2010147612A1 (en) | 2009-06-18 | 2010-12-23 | Lixte Biotechnology, Inc. | Methods of modulating cell regulation by inhibiting p53 |
| WO2010083617A1 (en) | 2009-01-21 | 2010-07-29 | Oncalis Ag | Pyrazolopyrimidines as protein kinase inhibitors |
| DK2391366T3 (da) | 2009-01-29 | 2013-01-07 | Novartis Ag | Substituerede benzimidazoler til behandling af astrocytomer |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| GB0903480D0 (en) * | 2009-02-27 | 2009-04-08 | Chroma Therapeutics Ltd | Enzyme Inhibitors |
| KR101168801B1 (ko) | 2009-03-27 | 2012-07-25 | 주식회사종근당 | 신규한 하이드록사메이트 유도체, 이의 제조방법, 및 이를 함유하는 약제학적 조성물 |
| EP2236503B1 (en) | 2009-04-03 | 2014-02-26 | NatureWise Biotech & Medicals Corporation | Cinamic compounds and derivatives therefrom for the inhibition of histone deacetylase |
| US7994357B2 (en) | 2009-04-03 | 2011-08-09 | Naturewise Biotech & Medicals Corporation | Cinamic compounds and derivatives therefrom for the inhibition of histone deacetylase |
| US8901337B2 (en) | 2009-07-16 | 2014-12-02 | Royal College Of Surgeons In Ireland | Metal complexes having dual histone deacetylase inhibitory and DNA-binding activity |
| US8389526B2 (en) | 2009-08-07 | 2013-03-05 | Novartis Ag | 3-heteroarylmethyl-imidazo[1,2-b]pyridazin-6-yl derivatives |
| WO2011019393A2 (en) | 2009-08-11 | 2011-02-17 | President And Fellows Of Harvard College | Class- and isoform-specific hdac inhibitors and uses thereof |
| CA2770873A1 (en) | 2009-08-12 | 2011-02-17 | Novartis Ag | Heterocyclic hydrazone compounds and their uses to treat cancer and inflammation |
| PE20121148A1 (es) | 2009-08-17 | 2012-09-07 | Intellikine Llc | Compuestos heterociclicos y usos de los mismos |
| BR112012008061A2 (pt) | 2009-08-20 | 2016-03-01 | Novartis Ag | compostos de oxima heterocíclica |
| IN2012DN01693A (Direct) | 2009-08-26 | 2015-06-05 | Novartis Ag | |
| US20110053925A1 (en) * | 2009-08-28 | 2011-03-03 | Novartis Ag | Hydroxamate-Based Inhibitors of Deacetylases |
| JO3002B1 (ar) | 2009-08-28 | 2016-09-05 | Irm Llc | مركبات و تركيبات كمثبطات كيناز بروتين |
| WO2011054828A1 (en) | 2009-11-04 | 2011-05-12 | Novartis Ag | Heterocyclic sulfonamide derivatives useful as mek inhibitors |
| BR112012012210B8 (pt) | 2009-11-23 | 2021-05-25 | Cerulean Pharma Inc | conjugado de (cdp)-taxano de polímero contendo ciclodextrina, composição, composição farmacêutica, forma de dosagem, kit e uso de um conjugado de cdp-taxano |
| JP5456908B2 (ja) | 2009-12-08 | 2014-04-02 | ノバルティス アーゲー | ヘテロ環式スルホンアミド誘導体 |
| US8440693B2 (en) | 2009-12-22 | 2013-05-14 | Novartis Ag | Substituted isoquinolinones and quinazolinones |
| CU24130B1 (es) | 2009-12-22 | 2015-09-29 | Novartis Ag | Isoquinolinonas y quinazolinonas sustituidas |
| WO2011084991A2 (en) * | 2010-01-08 | 2011-07-14 | President And Fellows Of Harvard College | Fluorinated hdac inhibitors and uses thereof |
| WO2011088192A1 (en) | 2010-01-13 | 2011-07-21 | Tempero Pharmaceuticals, Inc. | Compounds and methods |
| ES2560627T3 (es) | 2010-01-13 | 2016-02-22 | Tempero Pharmaceuticals, Inc. | Compuestos y procedimientos para la inhibición de HDAC |
| WO2011090940A1 (en) | 2010-01-19 | 2011-07-28 | Cerulean Pharma Inc. | Cyclodextrin-based polymers for therapeutic delivery |
| UY33236A (es) | 2010-02-25 | 2011-09-30 | Novartis Ag | Inhibidores dimericos de las iap |
| US8217079B2 (en) | 2010-03-26 | 2012-07-10 | Italfarmaco Spa | Method for treating Philadelphia-negative myeloproliferative syndromes |
| WO2011119995A2 (en) | 2010-03-26 | 2011-09-29 | Cerulean Pharma Inc. | Formulations and methods of use |
| UA112517C2 (uk) | 2010-07-06 | 2016-09-26 | Новартіс Аг | Тетрагідропіридопіримідинові похідні |
| EP2407164A1 (en) | 2010-07-14 | 2012-01-18 | Dublin Institute of Technology Intellectual Property Ltd | Copper II complexes of phenanthroline and their use in cancer treatment |
| WO2012025701A1 (en) * | 2010-08-25 | 2012-03-01 | Chroma Therapeutics Ltd. | Alpha, alpha - di substituted glycine ester derivatives and their use as hdac inhibitors |
| WO2012025155A1 (en) * | 2010-08-26 | 2012-03-01 | Novartis Ag | Hydroxamate-based inhibitors of deacetylases |
| CN103189353A (zh) * | 2010-08-27 | 2013-07-03 | 诺瓦提斯公司 | 基于异羟肟酸的脱乙酰酶抑制剂 |
| CN103261186A (zh) | 2010-12-13 | 2013-08-21 | 诺瓦提斯公司 | 二聚化iap抑制剂 |
| UY33794A (es) | 2010-12-13 | 2012-07-31 | Novartis Ag | Inhibidores diméricos de las iap |
| EP3239154A1 (en) | 2011-01-10 | 2017-11-01 | Nimbus Iris, Inc. | Irak inhibitors and uses thereof |
| TW201245115A (en) * | 2011-01-24 | 2012-11-16 | Chdi Foundation Inc | Histone deacetylase inhibitors and compositions and methods of use thereof |
| WO2012107500A1 (en) | 2011-02-10 | 2012-08-16 | Novartis Ag | [1, 2, 4] triazolo [4, 3 -b] pyridazine compounds as inhibitors of the c-met tyrosine kinase |
| EP2678016B1 (en) | 2011-02-23 | 2016-08-10 | Intellikine, LLC | Heterocyclic compounds and uses thereof |
| AR085397A1 (es) | 2011-02-23 | 2013-09-25 | Intellikine Inc | Combinacion de inhibidores de quinasa y sus usos |
| PL2683371T3 (pl) | 2011-03-09 | 2021-04-19 | Cereno Scientific Ab | Związki i sposoby poprawy zaburzonej funkcji wewnątrzustrojowej fibrynolizy przy zastosowaniu inhibitorów deacetylazy histonowej |
| EA201391820A1 (ru) | 2011-06-09 | 2014-12-30 | Новартис Аг | Гетероциклические сульфонамидные производные |
| SG195141A1 (en) | 2011-06-14 | 2013-12-30 | Novartis Ag | Combination of panobinostat and ruxolitinib in the treatment of cancer suchas a myeloproliferative neoplasm |
| EP2721007B1 (en) | 2011-06-20 | 2015-04-29 | Novartis AG | Cyclohexyl isoquinolinone compounds |
| EP2721008B1 (en) | 2011-06-20 | 2015-04-29 | Novartis AG | Hydroxy substituted isoquinolinone derivatives as p53 (mdm2 or mdm4) inhibitors |
| KR20140025530A (ko) | 2011-06-27 | 2014-03-04 | 노파르티스 아게 | 테트라히드로-피리도-피리미딘 유도체의 고체 형태 및 염 |
| US12194002B2 (en) | 2011-08-17 | 2025-01-14 | Dennis Brown | Compositions and methods to improve the therapeutic benefit of suboptimally administered chemical compounds including substituted hexitols such as dibromodulcitol |
| KR20140077916A (ko) | 2011-09-15 | 2014-06-24 | 노파르티스 아게 | 티로신 키나제로서의 6-치환된 3-(퀴놀린-6-일티오)-[1,2,4]트리아졸로[4,3-a]피라딘 |
| CA2855243C (en) | 2011-11-11 | 2020-04-14 | Novartis Ag | Method of treating a proliferative disease |
| ES2695099T3 (es) | 2011-11-23 | 2019-01-02 | Array Biopharma Inc | Formulaciones farmacéuticas |
| CN103130673B (zh) * | 2011-11-28 | 2017-05-03 | 重庆医药工业研究院有限责任公司 | 一种阿戈美拉晶型i的制备方法 |
| US8969341B2 (en) | 2011-11-29 | 2015-03-03 | Novartis Ag | Pyrazolopyrrolidine compounds |
| US9408885B2 (en) | 2011-12-01 | 2016-08-09 | Vib Vzw | Combinations of therapeutic agents for treating melanoma |
| SG11201402237WA (en) | 2011-12-22 | 2014-09-26 | Novartis Ag | Dihydro-benzo-oxazine and dihydro-pyrido-oxazine derivatives |
| WO2013093850A1 (en) | 2011-12-22 | 2013-06-27 | Novartis Ag | Quinoline derivatives |
| BR112014015308A8 (pt) | 2011-12-23 | 2017-06-13 | Novartis Ag | compostos para inibição da interação de bcl2 com contrapartes de ligação |
| US20130178520A1 (en) | 2011-12-23 | 2013-07-11 | Duke University | Methods of treatment using arylcyclopropylamine compounds |
| KR20140107578A (ko) | 2011-12-23 | 2014-09-04 | 노파르티스 아게 | Bcl2와 결합 파트너의 상호작용을 억제하기 위한 화합물 |
| AU2012355624A1 (en) | 2011-12-23 | 2014-07-17 | Novartis Ag | Compounds for inhibiting the interaction of BCL2 with binding partners |
| EA201491268A1 (ru) | 2011-12-23 | 2014-11-28 | Новартис Аг | Соединения и композиции для ингибирования взаимодействия bcl2 с партнерами по связыванию |
| EA201491264A1 (ru) | 2011-12-23 | 2014-11-28 | Новартис Аг | Соединения для ингибирования взаимодействия bcl-2 с партнерами по связыванию |
| AU2012362726A1 (en) * | 2011-12-29 | 2014-07-24 | Pharmacyclics Llc | Cinnamic acid hydroxyamides as inhibitors of histone deacetylase 8 |
| CN117736134A (zh) | 2012-01-12 | 2024-03-22 | 耶鲁大学 | 通过e3泛素连接酶增强靶蛋白质及其他多肽降解的化合物和方法 |
| UY34591A (es) | 2012-01-26 | 2013-09-02 | Novartis Ag | Compuestos de imidazopirrolidinona |
| AR092790A1 (es) * | 2012-02-01 | 2015-05-06 | Euro Celtique Sa | Derivados bencimidazolicos del acido hidroxamico |
| JP2015512425A (ja) | 2012-04-03 | 2015-04-27 | ノバルティス アーゲー | チロシンキナーゼ阻害剤との組合せ製品及びそれらの使用 |
| EA026559B1 (ru) | 2012-05-15 | 2017-04-28 | Новартис Аг | Соединения и композиции для ингибирования активности abl1, abl2 и bcr-abl1 |
| WO2013171640A1 (en) | 2012-05-15 | 2013-11-21 | Novartis Ag | Benzamide derivatives for inhibiting the activity of abl1, abl2 and bcr-abl1 |
| CA2868958C (en) | 2012-05-15 | 2020-09-01 | Novartis Ag | Benzamide derivatives for inhibiting the activity of abl1, abl2 and bcr-abl1 |
| US9340537B2 (en) | 2012-05-15 | 2016-05-17 | Novatis Ag | Benzamide derivatives for inhibiting the activity of ABL1, ABL2 and BCR-ABL1 |
| CN104321325B (zh) | 2012-05-24 | 2016-11-16 | 诺华股份有限公司 | 吡咯并吡咯烷酮化合物 |
| AU2013274101B2 (en) | 2012-06-15 | 2017-09-07 | The Brigham And Women's Hospital, Inc. | Compositions for treating cancer and methods for making the same |
| AR091773A1 (es) | 2012-07-16 | 2015-02-25 | Chdi Foundation Inc | Inhibidores de la histona desacetilasa y composiciones y sus metodos de uso |
| WO2014025395A1 (en) | 2012-08-06 | 2014-02-13 | Duke University | Compounds and methods for targeting hsp90 |
| CA3095019C (en) | 2012-10-02 | 2022-06-14 | Epitherapeutics Aps | Substituted pyridine derivatives and compositions thereof useful as inhibitors of histone demethylases |
| HRP20200521T1 (hr) | 2012-10-30 | 2020-08-07 | Mei Pharma, Inc. | Kombinacijske terapije za liječenje kemorezistentnih rakova |
| JP6374392B2 (ja) | 2012-11-05 | 2018-08-15 | デイナ ファーバー キャンサー インスティチュート，インコーポレイテッド | Ｘｂｐ１、ｃｄ１３８およびｃｓ１ペプチド、該ペプチドを含有する薬学的組成物、ならびにかかるペプチドおよび組成物を使用する方法 |
| UA115151C2 (uk) | 2012-11-08 | 2017-09-25 | Новартіс Аг | Фармацевтична комбінація, що містить інгібітор b-raf та інгібітор деацетилази гістонів, та її застосування при лікуванні проліферативних захворювань |
| TW201422625A (zh) | 2012-11-26 | 2014-06-16 | Novartis Ag | 二氫－吡啶并－□衍生物之固體形式 |
| US9403827B2 (en) | 2013-01-22 | 2016-08-02 | Novartis Ag | Substituted purinone compounds |
| US9556180B2 (en) | 2013-01-22 | 2017-01-31 | Novartis Ag | Pyrazolo[3,4-d]pyrimidinone compounds as inhibitors of the P53/MDM2 interaction |
| WO2014128612A1 (en) | 2013-02-20 | 2014-08-28 | Novartis Ag | Quinazolin-4-one derivatives |
| BR112015020650A2 (pt) | 2013-02-27 | 2017-07-18 | Epitherapeutics Aps | inibidores de histona demetilases |
| WO2014151147A1 (en) | 2013-03-15 | 2014-09-25 | Intellikine, Llc | Combination of kinase inhibitors and uses thereof |
| WO2014155268A2 (en) | 2013-03-25 | 2014-10-02 | Novartis Ag | Fgf-r tyrosine kinase activity inhibitors - use in diseases associated with lack of or reduced snf5 activity |
| JP2016519684A (ja) | 2013-04-08 | 2016-07-07 | デニス エム ブラウン | 準最適に投与された薬物療法の有効性を改善するための及び／又は副作用を低減するための方法および組成物 |
| JP2016516772A (ja) | 2013-04-09 | 2016-06-09 | リクスト・バイオテクノロジー，インコーポレイテッド | オキサシクロヘプタン及びオキサビシクロヘプテンの配合物 |
| WO2014178606A1 (en) | 2013-04-29 | 2014-11-06 | Chong Kun Dang Pharmaceutical Corp. | Novel compounds for selective histone deacetylase inhibitors, and pharmaceutical composition comprising the same |
| US20150018376A1 (en) | 2013-05-17 | 2015-01-15 | Novartis Ag | Pyrimidin-4-yl)oxy)-1h-indole-1-carboxamide derivatives and use thereof |
| GB201311891D0 (en) | 2013-07-03 | 2013-08-14 | Glaxosmithkline Ip Dev Ltd | Novel compound |
| GB201311888D0 (en) | 2013-07-03 | 2013-08-14 | Glaxosmithkline Ip Dev Ltd | Novel compounds |
| UY35675A (es) | 2013-07-24 | 2015-02-27 | Novartis Ag | Derivados sustituidos de quinazolin-4-ona |
| EP3024457A4 (en) | 2013-07-26 | 2017-06-28 | Update Pharma Inc. | Compositions to improve the therapeutic benefit of bisantrene |
| WO2015022663A1 (en) | 2013-08-14 | 2015-02-19 | Novartis Ag | Compounds and compositions as inhibitors of mek |
| WO2015022664A1 (en) | 2013-08-14 | 2015-02-19 | Novartis Ag | Compounds and compositions as inhibitors of mek |
| US9227969B2 (en) | 2013-08-14 | 2016-01-05 | Novartis Ag | Compounds and compositions as inhibitors of MEK |
| RU2683793C2 (ru) | 2013-09-22 | 2019-04-02 | Калитор Сайенсез, ЛЛС | Замещенные аминопиримидиновые соединения и способы их использования |
| EP3049442A4 (en) | 2013-09-26 | 2017-06-28 | Costim Pharmaceuticals Inc. | Methods for treating hematologic cancers |
| CN103467359B (zh) * | 2013-09-27 | 2015-04-22 | 山东大学 | 一种含有吲哚的肉桂酰胺类组蛋白去乙酰化酶抑制剂及其制备方法和应用 |
| TW201605450A (zh) | 2013-12-03 | 2016-02-16 | 諾華公司 | Ｍｄｍ２抑制劑與ＢＲＡＦ抑制劑之組合及其用途 |
| CN103664734B (zh) * | 2013-12-10 | 2015-09-23 | 广州康缔安生物科技有限公司 | 杂环羟肟酸类化合物及其药用组合物和应用 |
| TR201900057T4 (tr) | 2013-12-12 | 2019-01-21 | Chong Kun Dang Pharmaceutical Corp | Selektif histon deasetilaz (HDAC) inhibitörleri olarak yeni azaindol deriveleri ve bunları içeren farmasötik bileşimler. |
| KR101685639B1 (ko) | 2014-01-03 | 2016-12-12 | 주식회사 종근당 | 신규한 인돌 유도체 화합물 및 이를 포함하는 약제학적 조성물 |
| JOP20200094A1 (ar) | 2014-01-24 | 2017-06-16 | Dana Farber Cancer Inst Inc | جزيئات جسم مضاد لـ pd-1 واستخداماتها |
| JOP20200096A1 (ar) | 2014-01-31 | 2017-06-16 | Children’S Medical Center Corp | جزيئات جسم مضاد لـ tim-3 واستخداماتها |
| AU2015222865B2 (en) | 2014-02-28 | 2019-06-20 | Takeda Pharmaceutical Company Limited | TYK2 inhibitors and uses thereof |
| TWI898718B (zh) | 2014-03-14 | 2025-09-21 | 瑞士商諾華公司 | 針對lag-3之抗體分子及其用途 |
| WO2015148714A1 (en) | 2014-03-25 | 2015-10-01 | Duke University | Heat shock protein 70 (hsp-70) receptor ligands |
| EP3327006B1 (en) | 2014-03-28 | 2020-05-20 | Calitor Sciences, LLC | Substituted heteroaryl compounds and methods of use |
| AR099890A1 (es) | 2014-03-31 | 2016-08-24 | Epitherapeutics Aps | Inhibidores de histona demetilasas |
| AU2015241198A1 (en) | 2014-04-03 | 2016-11-17 | Invictus Oncology Pvt. Ltd. | Supramolecular combinatorial therapeutics |
| JP6778114B2 (ja) | 2014-04-14 | 2020-10-28 | アルビナス・オペレーションズ・インコーポレイテッドＡｒｖｉｎａｓ Ｏｐｅｒａｔｉｏｎｓ， Ｉｎｃ． | イミド系タンパク質分解モジュレーター及び関連する使用方法 |
| US20180228907A1 (en) | 2014-04-14 | 2018-08-16 | Arvinas, Inc. | Cereblon ligands and bifunctional compounds comprising the same |
| GB201409485D0 (en) | 2014-05-28 | 2014-07-09 | Euro Celtique Sa | Pharmaceutical composition |
| GB201409488D0 (en) | 2014-05-28 | 2014-07-09 | Euro Celtique Sa | Pharmaceutical composition |
| GB201409471D0 (en) | 2014-05-28 | 2014-07-09 | Euro Celtique Sa | Pharmaceutical composition |
| WO2016011658A1 (en) | 2014-07-25 | 2016-01-28 | Novartis Ag | Combination therapy |
| CN107207510B (zh) | 2014-07-31 | 2019-11-29 | 诺华股份有限公司 | 联合疗法 |
| US10071164B2 (en) | 2014-08-11 | 2018-09-11 | Yale University | Estrogen-related receptor alpha based protac compounds and associated methods of use |
| JP6749890B2 (ja) | 2014-08-12 | 2020-09-02 | モナッシュ ユニバーシティ | リンパ指向プロドラッグ |
| BR112017003442A2 (pt) | 2014-08-27 | 2017-11-28 | Gilead Sciences Inc | compostos e métodos para inibir histona desmetilases |
| EP2995630A1 (en) | 2014-09-09 | 2016-03-16 | Dublin Institute of Technology | Hybrid compounds formed from ionic liquids and uses thereof in ion selective electrodes |
| WO2016040892A1 (en) | 2014-09-13 | 2016-03-17 | Novartis Ag | Combination therapies |
| AU2015327868A1 (en) | 2014-10-03 | 2017-04-20 | Novartis Ag | Combination therapies |
| PL3215518T3 (pl) | 2014-10-29 | 2021-08-23 | Bicyclerd Limited | Bicykliczne ligandy peptydowe swoiste wobec MT1-MMP |
| EP3262049B1 (en) | 2015-02-27 | 2022-07-20 | Nimbus Lakshmi, Inc. | Tyk2 inhibitors and uses thereof |
| JP6692826B2 (ja) | 2015-03-10 | 2020-05-13 | アドゥロ バイオテック，インク． | 「インターフェロン遺伝子刺激因子」依存性シグナル伝達の活性化のための組成物及び方法 |
| MA41677A (fr) | 2015-03-13 | 2021-06-02 | Forma Therapeutics Inc | Composés alpha-cinnamide et compositions comme inhibiteurs de hdac8 |
| KR20230175343A (ko) | 2015-03-18 | 2023-12-29 | 아비나스 오퍼레이션스, 인코포레이티드 | 타겟화된 단백질들의 향상된 분해를 위한 화합물들 및 방법들 |
| PL3297992T3 (pl) | 2015-05-22 | 2020-07-27 | Chong Kun Dang Pharmaceutical Corp. | Heterocykloalkilowe związki pochodne jako selektywne inhibitory deacetylazy histonowej oraz zawierające je kompozycje farmaceutyczne |
| WO2017004133A1 (en) | 2015-06-29 | 2017-01-05 | Nimbus Iris, Inc. | Irak inhibitors and uses thereof |
| WO2017004134A1 (en) | 2015-06-29 | 2017-01-05 | Nimbus Iris, Inc. | Irak inhibitors and uses thereof |
| WO2017024318A1 (en) | 2015-08-06 | 2017-02-09 | Dana-Farber Cancer Institute, Inc. | Targeted protein degradation to attenuate adoptive t-cell therapy associated adverse inflammatory responses |
| WO2017032281A1 (zh) * | 2015-08-21 | 2017-03-02 | 苏州晶云药物科技有限公司 | 帕比司他乳酸盐的新晶型 |
| WO2017040757A1 (en) | 2015-09-02 | 2017-03-09 | Nimbus Lakshmi, Inc. | Tyk2 inhibitors and uses thereof |
| EP3347340A4 (en) | 2015-09-08 | 2019-01-23 | Monash University | LYMPHENLEITUNGSPRODRUGS |
| US9938257B2 (en) | 2015-09-11 | 2018-04-10 | Calitor Sciences, Llc | Substituted heteroaryl compounds and methods of use |
| CA3234750A1 (en) | 2015-10-23 | 2017-04-27 | Navitor Pharmaceuticals, Inc. | Modulators of sestrin-gator2 interaction and uses thereof |
| US9938264B2 (en) | 2015-11-02 | 2018-04-10 | Yale University | Proteolysis targeting chimera compounds and methods of preparing and using same |
| ITUB20155193A1 (it) | 2015-11-03 | 2017-05-03 | Italfarmaco Spa | Sospensioni orali di Givinostat fisicamente e chimicamente stabili |
| ES2907489T3 (es) | 2015-12-14 | 2022-04-25 | X4 Pharmaceuticals Inc | Métodos para el tratamiento del cáncer |
| WO2017106332A1 (en) | 2015-12-14 | 2017-06-22 | X4 Pharmaceuticals, Inc. | Methods for treating cancer |
| EP3389664A4 (en) | 2015-12-14 | 2020-01-08 | Raze Therapeutics Inc. | MTHFD2 CAFFEIN INHIBITORS AND USES THEREOF |
| CN108883091A (zh) | 2015-12-22 | 2018-11-23 | X4 制药有限公司 | 用于治疗免疫缺陷病的方法 |
| CN105732467A (zh) * | 2016-01-13 | 2016-07-06 | 深圳市康立生生物科技有限公司 | 一种panobinostat(帕比司他)的制备方法 |
| PT3426243T (pt) | 2016-03-09 | 2021-08-19 | Raze Therapeutics Inc | Inibidores de 3-fosfoglicerato desidrogenase e utilizações dos mesmos |
| EP3426244B1 (en) | 2016-03-09 | 2023-06-07 | Raze Therapeutics, Inc. | 3-phosphoglycerate dehydrogenase inhibitors and uses thereof |
| SG10201913331VA (en) | 2016-03-15 | 2020-03-30 | Oryzon Genomics Sa | Combinations of lsd1 inhibitors for use in the treatment of solid tumors |
| EP3429570A1 (en) | 2016-03-15 | 2019-01-23 | Oryzon Genomics, S.A. | Combinations of lsd1 inhibitors for the treatment of hematological malignancies |
| CN109153722A (zh) | 2016-04-08 | 2019-01-04 | X4 制药有限公司 | 用于治疗癌症的方法 |
| US11261187B2 (en) | 2016-04-22 | 2022-03-01 | Duke University | Compounds and methods for targeting HSP90 |
| AR108257A1 (es) | 2016-05-02 | 2018-08-01 | Mei Pharma Inc | Formas polimórficas de 3-[2-butil-1-(2-dietilamino-etil)-1h-bencimidazol-5-il]-n-hidroxi-acrilamida y usos de las mismas |
| WO2017197036A1 (en) | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | Spirocyclic degronimers for target protein degradation |
| EP3455218A4 (en) | 2016-05-10 | 2019-12-18 | C4 Therapeutics, Inc. | C3 CARBON-BASED GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN REDUCTION |
| WO2017197055A1 (en) | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | Heterocyclic degronimers for target protein degradation |
| EP3455219A4 (en) | 2016-05-10 | 2019-12-18 | C4 Therapeutics, Inc. | AMINE-RELATED C3-GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN REDUCTION |
| WO2017223239A1 (en) | 2016-06-21 | 2017-12-28 | X4 Pharmaceuticals, Inc. | Cxcr4 inhibitors and uses thereof |
| US11332470B2 (en) | 2016-06-21 | 2022-05-17 | X4 Pharmaceuticals, Inc. | CXCR4 inhibitors and uses thereof |
| EP3471726A4 (en) | 2016-06-21 | 2019-10-09 | X4 Pharmaceuticals, Inc. | CXCR4 INHIBITORS AND USES THEREOF |
| AU2017280099A1 (en) * | 2016-06-21 | 2019-01-17 | The University Of Melbourne | Activators of HIV latency |
| WO2018015493A1 (en) | 2016-07-20 | 2018-01-25 | Royal College Of Surgeons In Ireland | Metal complexes having therapeutic applications |
| WO2018039203A1 (en) | 2016-08-23 | 2018-03-01 | Oncopep, Inc. | Peptide vaccines and durvalumab for treating multiple myeloma |
| CA3034666A1 (en) | 2016-08-23 | 2018-03-01 | Oncopep, Inc. | Peptide vaccines and durvalumab for treating breast cancer |
| WO2018054960A1 (en) | 2016-09-21 | 2018-03-29 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for predicting and treating resistance to chemotherapy in npm-alk(+) alcl |
| US10927083B2 (en) | 2016-09-29 | 2021-02-23 | Duke University | Substituted benzimidazoles as inhibitors of transforming growth factor-β kinase |
| US10207998B2 (en) | 2016-09-29 | 2019-02-19 | Duke University | Substituted benzimidazole and substituted benzothiazole inhibitors of transforming growth factor-β kinase and methods of use thereof |
| CA3040155C (en) | 2016-10-11 | 2024-01-16 | Euro-Celtique S.A. | Compound for use in the treatment of hodgkin lymphoma |
| CN109952303B (zh) | 2016-10-14 | 2022-10-21 | 林伯士拉克许米公司 | Tyk2抑制剂及其用途 |
| US10647713B2 (en) | 2016-10-21 | 2020-05-12 | Nimbus Lakshmi, Inc. | TYK2 inhibitors and uses thereof |
| WO2018089499A1 (en) | 2016-11-08 | 2018-05-17 | Navitor Pharmaceuticals, Inc. | PHENYL AMINO PIPERIDINE mTORC INHIBITORS AND USES THEREOF |
| EP3548005A4 (en) | 2016-11-29 | 2020-06-17 | Puretech Health LLC | Exosomes for delivery of therapeutic agents |
| WO2018106636A1 (en) | 2016-12-05 | 2018-06-14 | Raze Therapeutics, Inc. | Shmt inhibitors and uses thereof |
| CN110234647B (zh) | 2016-12-08 | 2023-05-23 | 利克斯特生物技术公司 | 用于调节免疫应答的氧杂双环庚烷 |
| JP2020502238A (ja) | 2016-12-23 | 2020-01-23 | バイスクルアールディー・リミテッド | 新規連結構造を有するペプチド誘導体 |
| WO2018127699A1 (en) | 2017-01-06 | 2018-07-12 | Bicyclerd Limited | Compounds for treating cancer |
| IL312367A (en) | 2017-01-31 | 2024-06-01 | Arvinas Operations Inc | Cereblon ligands and bifunctional compounds comprising the same |
| WO2018148440A1 (en) | 2017-02-08 | 2018-08-16 | Dana-Farber Cancer Institute, Inc. | Regulating chimeric antigen receptors |
| AU2018230737B2 (en) | 2017-03-08 | 2022-09-22 | Takeda Pharmaceutical Company Limited | Tyk2 inhibitors, uses, and methods for production thereof |
| EP3375778A1 (en) | 2017-03-14 | 2018-09-19 | Artax Biopharma Inc. | Aryl-piperidine derivatives |
| EP3375784A1 (en) | 2017-03-14 | 2018-09-19 | Artax Biopharma Inc. | Aza-dihydro-acridone derivatives |
| US11339144B2 (en) | 2017-04-10 | 2022-05-24 | Navitor Pharmaceuticals, Inc. | Heteroaryl Rheb inhibitors and uses thereof |
| JOP20180036A1 (ar) | 2017-04-18 | 2019-01-30 | Vifor Int Ag | أملاح لمثبطات فروبورتين جديدة |
| WO2018197893A1 (en) | 2017-04-27 | 2018-11-01 | Bicycletx Limited | Bicyclic peptide ligands and uses thereof |
| UY37695A (es) | 2017-04-28 | 2018-11-30 | Novartis Ag | Compuesto dinucleótido cíclico bis 2’-5’-rr-(3’f-a)(3’f-a) y usos del mismo |
| CN107141244B (zh) * | 2017-05-08 | 2019-11-19 | 潍坊医学院 | 吲哚丁酸类组蛋白去乙酰酶抑制剂及其制备方法和应用 |
| GB201709405D0 (en) | 2017-06-13 | 2017-07-26 | Euro Celtique Sa | Compounds for treating ovarian cancer |
| GB201709402D0 (en) | 2017-06-13 | 2017-07-26 | Euro Celtique Sa | Compounds for treating t-pll |
| GB201709406D0 (en) | 2017-06-13 | 2017-07-26 | Euro-Cletique S A | Compounds for treating TNBC |
| GB201709403D0 (en) | 2017-06-13 | 2017-07-26 | Euro Celtique Sa | Compounds for treating sarcoma |
| CN118440096A (zh) | 2017-06-20 | 2024-08-06 | C4医药公司 | 用于蛋白降解的n/o-连接的降解决定子和降解决定子体 |
| JP7301757B2 (ja) | 2017-06-26 | 2023-07-03 | バイスクルアールディー・リミテッド | 検出可能部分を持つ二環式ペプチドリガンドおよびその使用 |
| EP4438117A3 (en) | 2017-07-28 | 2024-12-18 | Takeda Pharmaceutical Company Limited | Tyk2 inhibitors and uses thereof |
| CN118772242A (zh) | 2017-08-04 | 2024-10-15 | 拜斯科技术开发有限公司 | Cd137特异性的双环肽配体 |
| KR101977970B1 (ko) | 2017-08-04 | 2019-05-14 | 중원대학교 산학협력단 | 신규한 벤즈아미드계 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 암 예방 또는 치료용 약학 조성물 |
| WO2019034868A1 (en) | 2017-08-14 | 2019-02-21 | Bicyclerd Limited | CONJUGATES PEPTIDE BICYCLIC-LIGAND PPR-A AND USES THEREOF |
| US20200291096A1 (en) | 2017-08-14 | 2020-09-17 | Bicyclerd Limited | Bicyclic peptide ligand sting conjugates and uses thereof |
| US11883497B2 (en) | 2017-08-29 | 2024-01-30 | Puretech Lyt, Inc. | Lymphatic system-directing lipid prodrugs |
| EP4306524A3 (en) | 2017-08-29 | 2024-09-11 | PureTech LYT, Inc. | Lymphatic system-directing lipid prodrugs |
| WO2019060693A1 (en) | 2017-09-22 | 2019-03-28 | Kymera Therapeutics, Inc. | CRBN LIGANDS AND USES THEREOF |
| IL295603B2 (en) | 2017-09-22 | 2024-03-01 | Kymera Therapeutics Inc | Protein degraders and uses thereof |
| EP3461488A1 (en) | 2017-09-27 | 2019-04-03 | Onxeo | Combination of a dbait molecule and a hdac inhibitor for treating cancer |
| EP3461480A1 (en) | 2017-09-27 | 2019-04-03 | Onxeo | Combination of a dna damage response cell cycle checkpoint inhibitors and belinostat for treating cancer |
| WO2019084026A1 (en) | 2017-10-24 | 2019-05-02 | Genentech, Inc. | (4-HYDROXYPYRROLIDIN-2-YL) -HETEROCYCLIC COMPOUNDS AND METHODS OF USE |
| WO2019083960A1 (en) | 2017-10-24 | 2019-05-02 | Oncopep, Inc. | PEPTIDE VACCINES AND HDAC INHIBITORS FOR THE TREATMENT OF MULTIPLE MYELOMA |
| WO2019084030A1 (en) | 2017-10-24 | 2019-05-02 | Genentech, Inc. | (4-HYDROXYPYRROLIDIN-2-YL) -HYDROXAMATE COMPOUNDS AND METHODS OF USE |
| AU2018353984A1 (en) | 2017-10-24 | 2020-05-07 | Oncopep, Inc. | Peptide vaccines and pembrolizumab for treating breast cancer |
| WO2019099311A1 (en) | 2017-11-19 | 2019-05-23 | Sunshine Lake Pharma Co., Ltd. | Substituted heteroaryl compounds and methods of use |
| US10537585B2 (en) | 2017-12-18 | 2020-01-21 | Dexcel Pharma Technologies Ltd. | Compositions comprising dexamethasone |
| US11304954B2 (en) | 2017-12-19 | 2022-04-19 | Puretech Lyt, Inc. | Lipid prodrugs of mycophenolic acid and uses thereof |
| US11608345B1 (en) | 2017-12-19 | 2023-03-21 | Puretech Lyt, Inc. | Lipid prodrugs of rapamycin and its analogs and uses thereof |
| US11602534B2 (en) | 2017-12-21 | 2023-03-14 | Hefei Institutes Of Physical Science, Chinese Academy Of Sciences | Pyrimidine derivative kinase inhibitors |
| IL315310A (en) | 2017-12-26 | 2024-10-01 | Kymera Therapeutics Inc | Irak degraders and uses thereof |
| US11512080B2 (en) | 2018-01-12 | 2022-11-29 | Kymera Therapeutics, Inc. | CRBN ligands and uses thereof |
| US11485743B2 (en) | 2018-01-12 | 2022-11-01 | Kymera Therapeutics, Inc. | Protein degraders and uses thereof |
| AU2019209960B2 (en) | 2018-01-20 | 2023-11-23 | Sunshine Lake Pharma Co., Ltd. | Substituted aminopyrimidine compounds and methods of use |
| BR112020015328A2 (pt) | 2018-01-29 | 2020-12-08 | Merck Patent Gmbh | Inibidores de gcn2 e usos dos mesmos |
| CN117659010A (zh) | 2018-01-29 | 2024-03-08 | 默克专利股份有限公司 | Gcn2抑制剂及其用途 |
| FI3752182T3 (fi) | 2018-02-12 | 2024-07-30 | Inimmune Corp | Tollin kaltaisen reseptorin ligandeja |
| BR112020014576A2 (pt) | 2018-02-23 | 2020-12-08 | Bicycletx Limited | Ligantes peptídicos bicíclicos multiméricos |
| EP3759086A1 (en) | 2018-02-27 | 2021-01-06 | Artax Biopharma Inc. | Chromene derivatives as inhibitors of tcr-nck interaction |
| WO2019183523A1 (en) | 2018-03-23 | 2019-09-26 | Genentech, Inc. | Hetero-bifunctional degrader compounds and their use as modulators of targeted ubiquination (vhl) |
| MX2020010571A (es) | 2018-04-13 | 2021-01-08 | Arvinas Operations Inc | Ligandos de cereblon y compuestos bifuncionales que los comprenden. |
| US11059826B2 (en) | 2018-04-24 | 2021-07-13 | Vertex Pharmaceuticals Incorporated | Pteridinone compounds and uses thereof |
| PT3784666T (pt) | 2018-04-24 | 2022-06-06 | Merck Patent Gmbh | Compostos antiproliferação e utilizações dos mesmos |
| EP3807263A1 (en) | 2018-06-13 | 2021-04-21 | Amphista Therapeutics Ltd | Bifunctional molecules for targeting uchl5 |
| JP2021527137A (ja) | 2018-06-13 | 2021-10-11 | アンフィスタ セラピューティクス リミテッド | Ｒｐｎ１１を標的化するための二機能性分子 |
| WO2019238886A1 (en) | 2018-06-13 | 2019-12-19 | University Of Dundee | Bifunctional molecules for targeting usp14 |
| LT3813946T (lt) | 2018-06-15 | 2024-07-10 | Janssen Pharmaceutica Nv | Rapamicino analogai ir jų panaudojimas |
| US11180531B2 (en) | 2018-06-22 | 2021-11-23 | Bicycletx Limited | Bicyclic peptide ligands specific for Nectin-4 |
| EP3817822A4 (en) | 2018-07-06 | 2022-07-27 | Kymera Therapeutics, Inc. | PROTEIN DEGRADANTS AND USES THEREOF |
| WO2020010177A1 (en) | 2018-07-06 | 2020-01-09 | Kymera Therapeutics, Inc. | Tricyclic crbn ligands and uses thereof |
| CN108752255A (zh) * | 2018-07-19 | 2018-11-06 | 重庆医科大学 | 一种帕比司他及其关键中间体的制备方法 |
| EP3826988A4 (en) | 2018-07-24 | 2023-03-22 | Hygia Pharmaceuticals, LLC | COMPOUNDS, DERIVATIVES AND ANALOGUES FOR CANCER |
| US10548889B1 (en) | 2018-08-31 | 2020-02-04 | X4 Pharmaceuticals, Inc. | Compositions of CXCR4 inhibitors and methods of preparation and use |
| US12030875B2 (en) | 2018-09-07 | 2024-07-09 | PIC Therapeutics, Inc. | EIF4E inhibitors and uses thereof |
| EP3866789A4 (en) | 2018-10-15 | 2022-07-06 | Nimbus Lakshmi, Inc. | TYK2 INHIBITORS AND USES THEREOF |
| CN112955459A (zh) | 2018-10-23 | 2021-06-11 | 拜斯科技术开发有限公司 | 双环肽配体和其用途 |
| CN109574936B (zh) * | 2018-11-23 | 2022-02-22 | 沈阳药科大学 | 一种具有hdac6抑制活性的异羟肟酸类化合物及其应用 |
| CA3120866A1 (en) | 2018-11-30 | 2020-06-04 | Nimbus Lakshmi, Inc. | Tyk2 inhibitors and uses thereof |
| PH12021500026A1 (en) | 2018-11-30 | 2022-05-11 | Kymera Therapeutics Inc | Irak degraders and uses thereof |
| GB201820288D0 (en) | 2018-12-13 | 2019-01-30 | Bicycle Tx Ltd | Bicycle peptide ligaands specific for MT1-MMP |
| GB201820325D0 (en) | 2018-12-13 | 2019-01-30 | Bicyclerd Ltd | Bicyclic peptide ligands specific for psma |
| GB201820295D0 (en) | 2018-12-13 | 2019-01-30 | Bicyclerd Ltd | Bicyclic peptide ligands specific for MT1-MMP |
| EP3897626B1 (en) | 2018-12-18 | 2025-09-10 | Mundipharma International Corporation Limited | Tinostamustine for treating multiple myeloma |
| CN120698985A (zh) | 2018-12-20 | 2025-09-26 | C4医药公司 | 靶向蛋白降解 |
| EP3670659A1 (en) | 2018-12-20 | 2020-06-24 | Abivax | Biomarkers, and uses in treatment of viral infections, inflammations, or cancer |
| JP2022514618A (ja) | 2018-12-21 | 2022-02-14 | バイスクルテクス・リミテッド | Ｐｄ－ｌ１に特異的な二環式ペプチドリガンド |
| WO2020154474A1 (en) | 2019-01-23 | 2020-07-30 | Nimbus Lakshmi, Inc. | Tyk2 inhibitors and uses thereof |
| WO2020165600A1 (en) | 2019-02-14 | 2020-08-20 | Bicycletx Limited | Bicyclic peptide ligand sting conjugates and uses thereof |
| US20220184222A1 (en) | 2019-04-02 | 2022-06-16 | Bicycletx Limited | Bicycle toxin conjugates and uses thereof |
| CN113939300A (zh) | 2019-04-05 | 2022-01-14 | 凯麦拉医疗公司 | Stat降解剂和其用途 |
| US11458149B1 (en) | 2019-05-31 | 2022-10-04 | Ikena Oncology, Inc. | TEAD inhibitors and uses thereof |
| GB201913124D0 (en) | 2019-09-11 | 2019-10-23 | Seald As | Compositions and methods for treatment of cholangiocarcinoma |
| GB201913121D0 (en) | 2019-09-11 | 2019-10-23 | Seald As | Compositions and methods for treatment of cholangiocarcinoma |
| GB201913122D0 (en) | 2019-09-11 | 2019-10-23 | Seald As | Compositions and methods for treatment of cholangiocarcinoma |
| GB201913123D0 (en) | 2019-09-11 | 2019-10-23 | Seald As | Compositions and methods for treatment of cholangiocarcinoma |
| CN115038688A (zh) | 2019-09-11 | 2022-09-09 | 文森雷生物科学股份有限公司 | Usp30抑制剂及其用途 |
| AU2020347274A1 (en) | 2019-09-13 | 2022-03-31 | Nimbus Saturn, Inc. | HPK1 antagonists and uses thereof |
| EP3798250A1 (en) | 2019-09-25 | 2021-03-31 | University College Dublin | Hyperbranched cationic polymers useful as nucleic acid delivery vectors for transfecting |
| BR112022005412A2 (pt) | 2019-09-25 | 2022-06-21 | Univ Dublin | Composições nanoparticuladas para terapia gênica |
| CA3152582A1 (en) * | 2019-11-06 | 2021-05-14 | Dana-Farber Cancer Institute, Inc. | Selective histone deacetylase (hdac) degraders and methods of use thereof |
| KR20220128345A (ko) | 2019-12-05 | 2022-09-20 | 아나쿠리아 테라퓨틱스, 인코포레이티드 | 라파마이신 유사체 및 이의 용도 |
| US11591332B2 (en) | 2019-12-17 | 2023-02-28 | Kymera Therapeutics, Inc. | IRAK degraders and uses thereof |
| IL293917A (en) | 2019-12-17 | 2022-08-01 | Kymera Therapeutics Inc | Irak degraders and uses thereof |
| CR20220353A (es) | 2019-12-19 | 2022-10-20 | Arvinas Operations Inc | Compuestos y métodos para la degradación dirigida del receptor de andrógenos |
| BR112022012410A2 (pt) | 2019-12-23 | 2022-08-30 | Kymera Therapeutics Inc | Degradadores smarca e usos dos mesmos |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| IL295362A (en) | 2020-02-05 | 2022-10-01 | Puretech Lyt Inc | Lipid prodrugs of neurosteroids |
| IT202000004075A1 (it) * | 2020-02-27 | 2021-08-27 | Flamma Spa | Processo per la preparazione di panobinostat |
| TW202146393A (zh) | 2020-03-03 | 2021-12-16 | 美商皮克醫療公司 | Eif4e抑制劑及其用途 |
| EP4117662A4 (en) | 2020-03-10 | 2024-04-03 | X4 Pharmaceuticals, Inc. | METHODS OF TREATING NEUTROPENIA |
| WO2021185844A1 (en) | 2020-03-16 | 2021-09-23 | Pvac Medical Technologies Ltd | Use of substance and pharmaceutical composition thereof, and medical treatments or uses thereof |
| WO2021233534A1 (en) | 2020-05-20 | 2021-11-25 | Pvac Medical Technologies Ltd | Use of substance and pharmaceutical composition thereof, and medical treatments or uses thereof |
| PH12022552458A1 (en) | 2020-03-19 | 2024-01-22 | Kymera Therapeutics Inc | Mdm2 degraders and uses thereof |
| US12359208B2 (en) | 2020-04-15 | 2025-07-15 | California Institute Of Technology | Thermal control of T-cell immunotherapy through molecular and physical actuation |
| US20230250110A1 (en) | 2020-06-03 | 2023-08-10 | Kymera Therapeutics, Inc. | Deuterated irak degraders and uses thereof |
| TW202210483A (zh) | 2020-06-03 | 2022-03-16 | 美商凱麥拉醫療公司 | Irak降解劑之結晶型 |
| EP4192509A1 (en) | 2020-08-05 | 2023-06-14 | Ellipses Pharma Ltd | Treatment of cancer using a cyclodextrin-containing polymer-topoisomerase inhibitor conjugate and a parp inhibitor |
| JP2023538906A (ja) | 2020-08-17 | 2023-09-12 | バイシクルティーエクス・リミテッド | ネクチン－４に特異的な二環コンジュゲート及びその使用 |
| WO2022047259A1 (en) | 2020-08-28 | 2022-03-03 | California Institute Of Technology | Synthetic mammalian signaling circuits for robust cell population control |
| WO2022087634A1 (en) | 2020-10-23 | 2022-04-28 | Nimbus Clotho, Inc. | Ctps1 inhibitors and uses thereof |
| WO2022120354A1 (en) | 2020-12-02 | 2022-06-09 | Ikena Oncology, Inc. | Tead inhibitors and uses thereof |
| WO2022120353A1 (en) | 2020-12-02 | 2022-06-09 | Ikena Oncology, Inc. | Tead inhibitors and uses thereof |
| MX2023007032A (es) | 2020-12-18 | 2023-07-18 | Amphista Therapeutics Ltd | Moléculas bifuncionales novedosas para la degradación de proteínas dirigidas. |
| GB202020359D0 (en) | 2020-12-22 | 2021-02-03 | Midatech Pharma Wales Ltd | Pharmaceutical compositions and use thereof in combination therapy for brain cancer |
| CN116867758A (zh) | 2020-12-30 | 2023-10-10 | 凯麦拉医疗公司 | Irak降解剂和其用途 |
| CA3206501A1 (en) | 2021-02-02 | 2022-08-11 | Shaun Abbott | Gpr84 antagonists and uses thereof |
| WO2022167445A1 (en) | 2021-02-02 | 2022-08-11 | Liminal Biosciences Limited | Gpr84 antagonists and uses thereof |
| MX2023009527A (es) | 2021-02-15 | 2023-08-24 | Kymera Therapeutics Inc | Degradadores de la cinasa 4 asociada al receptor de interleucina 1 (irak4) y usos de los mismos. |
| WO2022217276A1 (en) | 2021-04-09 | 2022-10-13 | Nimbus Clio, Inc. | Cbl-b modulators and uses thereof |
| IL307673A (en) | 2021-04-16 | 2023-12-01 | Ikena Oncology Inc | MEK inhibitors and their use |
| AU2022271290A1 (en) | 2021-05-07 | 2023-11-23 | Kymera Therapeutics, Inc. | Cdk2 degraders and uses thereof |
| EP4392421A1 (en) | 2021-08-25 | 2024-07-03 | PIC Therapeutics, Inc. | Eif4e inhibitors and uses thereof |
| CA3229560A1 (en) | 2021-08-25 | 2023-03-02 | Christopher L. Vandeusen | Eif4e inhibitors and uses thereof |
| US20250134952A1 (en) | 2021-09-20 | 2025-05-01 | Institut National de la Santé et de la Recherche Médicale | Methods for improving the efficacy of hdac inhibitor therapy and predicting the response to treatment with hdac inhibitor |
| GB2611043A (en) | 2021-09-22 | 2023-03-29 | Univ Dublin City | A cis-platinum(II)-oligomer hybrid |
| KR20240110592A (ko) | 2021-10-29 | 2024-07-15 | 카이메라 쎄라퓨틱스 인코포레이티드 | Irak4 분해제 및 이의 합성 |
| CN118632688A (zh) | 2021-11-19 | 2024-09-10 | 布朗卡布努斯有限公司 | 一种包含包装在药物递送载体中的治疗活性剂的组合物 |
| WO2023114984A1 (en) | 2021-12-17 | 2023-06-22 | Ikena Oncology, Inc. | Tead inhibitors and uses thereof |
| CA3243560A1 (en) | 2022-01-31 | 2023-08-03 | Kymera Therapeutics, Inc. | Iraqi Degradation Agents and Their Uses |
| WO2023173053A1 (en) | 2022-03-10 | 2023-09-14 | Ikena Oncology, Inc. | Mek inhibitors and uses thereof |
| WO2023173057A1 (en) | 2022-03-10 | 2023-09-14 | Ikena Oncology, Inc. | Mek inhibitors and uses thereof |
| WO2023194441A1 (en) | 2022-04-05 | 2023-10-12 | Istituto Nazionale Tumori Irccs - Fondazione G. Pascale | Combination of hdac inhibitors and statins for use in the treatment of pancreatic cancer |
| GB2617409B (en) | 2022-04-27 | 2024-06-26 | Cancertain Ltd | Method for predicting responsiveness to therapy |
| WO2023211889A1 (en) | 2022-04-25 | 2023-11-02 | Ikena Oncology, Inc. | Polymorphic compounds and uses thereof |
| TW202404581A (zh) | 2022-05-25 | 2024-02-01 | 美商醫肯納腫瘤學公司 | Ｍｅｋ抑制劑及其用途 |
| CN119384408A (zh) | 2022-06-16 | 2025-01-28 | 安菲斯塔治疗有限责任公司 | 用于靶向蛋白降解的双功能分子 |
| KR20250065819A (ko) | 2022-08-02 | 2025-05-13 | 국립대학법인 홋가이도 다이가쿠 | 소기관 복합체를 이용한 세포 치료 개선 방법 |
| KR20250057800A (ko) | 2022-08-02 | 2025-04-29 | 리미널 바이오사이언시스 리미티드 | 헤테로아릴 카복스아마이드 및 관련 gpr84 길항제 및 이의 용도 |
| CN119894873A (zh) | 2022-08-02 | 2025-04-25 | 里米诺生物科学有限公司 | 芳基三唑基和相关gpr84拮抗剂及其用途 |
| IL318576A (en) | 2022-08-02 | 2025-03-01 | Liminal Biosciences Ltd | Pyridoxine-substituted GPR84 antagonists and their uses |
| WO2024041744A1 (en) | 2022-08-26 | 2024-02-29 | Biodexa Ltd. | Combination therapy for brain cancer |
| WO2024112894A1 (en) | 2022-11-22 | 2024-05-30 | PIC Therapeutics, Inc. | Eif4e inhibitors and uses thereof |
| CN120916756A (zh) | 2023-03-03 | 2025-11-07 | 伊昂克图拉股份有限公司 | 用于治疗血液恶性肿瘤的罗吉诺利西布与hdac抑制剂的组合 |
| EP4620470A3 (en) | 2023-06-23 | 2025-10-08 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| WO2025026925A1 (en) | 2023-07-28 | 2025-02-06 | Ospedale San Raffaele S.R.L. | Gtf2i inhibitors and uses thereof |
| CN119490449B (zh) * | 2023-08-16 | 2025-11-21 | 沈阳药科大学 | 含n-苄基-2-(5-苯基吡啶-2-基)乙酰胺的异羟肟酸类化合物及制备方法和应用 |
| WO2025062372A1 (en) | 2023-09-21 | 2025-03-27 | Takeda Pharmaceutical Company Limited | Tyk2 inhibitors for use in the treatment of inflammatory bowel disease |
| WO2025078542A1 (en) | 2023-10-11 | 2025-04-17 | Technological University Dublin | Coumarin-metal complexes and uses thereof |
| CN118027033A (zh) * | 2024-01-26 | 2024-05-14 | 四川大学 | 一种hdac6抑制剂及其制备方法和在抗炎和溃疡性结肠炎中的用途 |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5700811A (en) * | 1991-10-04 | 1997-12-23 | Sloan-Kettering Institute For Cancer Research | Potent inducers of terminal differentiation and method of use thereof |
| WO1993012075A1 (fr) | 1991-12-10 | 1993-06-24 | Shionogi & Co., Ltd. | Derive d'acide hydroxamique a base de sulfonamide aromatique |
| GB9215665D0 (en) * | 1992-07-23 | 1992-09-09 | British Bio Technology | Compounds |
| US5569668A (en) * | 1995-03-29 | 1996-10-29 | Webster; John M. | Indole derivatives with antibacterial and antimycotic properties |
| US5722242A (en) * | 1995-12-15 | 1998-03-03 | Borealis Technical Limited | Method and apparatus for improved vacuum diode heat pump |
| US6777217B1 (en) | 1996-03-26 | 2004-08-17 | President And Fellows Of Harvard College | Histone deacetylases, and uses related thereto |
| JPH10182583A (ja) | 1996-12-25 | 1998-07-07 | Mitsui Chem Inc | 新規ヒドロキサム酸誘導体 |
| AUPO721997A0 (en) * | 1997-06-06 | 1997-07-03 | Queensland Institute Of Medical Research, The | Anticancer compounds |
| US6127392A (en) * | 1997-08-05 | 2000-10-03 | American Home Products Corporation | Anthranilic acid analogs |
| BR9811845A (pt) | 1997-08-05 | 2000-08-08 | American Home Prod | Análogos do ácido antranìlico |
| JP2002528391A (ja) | 1998-10-19 | 2002-09-03 | メチルジェン，インク． | 組合せ治療による遺伝子発現の修飾 |
| US6110922A (en) | 1998-12-29 | 2000-08-29 | Abbott Laboratories | Cell adhesion-inhibiting antiinflammatory and immune-suppressive compounds |
| UA74781C2 (en) | 1999-04-02 | 2006-02-15 | Abbott Lab | Antiinflammatory and immumosuppressive compounds inhibiting cell adhesion |
| UA74345C2 (uk) | 1999-09-08 | 2005-12-15 | Слоан-Кеттерінг Інстітьют Фо Кансер Рісерч | Засоби клітинної диференціації і інгібітори гістонової деацетилази та способи їх використання |
| GB9922173D0 (en) | 1999-09-21 | 1999-11-17 | Zeneca Ltd | Chemical compounds |
| EP1233958B1 (en) * | 1999-11-23 | 2011-06-29 | MethylGene Inc. | Inhibitors of histone deacetylase |
| JP2003516144A (ja) | 1999-12-08 | 2003-05-13 | アクシス・ファーマシューティカルズ・インコーポレイテッド | ヒストン脱アセチル化酵素−８のタンパク質、核酸およびその使用方法 |
| TW427572U (en) * | 1999-12-17 | 2001-03-21 | Hon Hai Prec Ind Co Ltd | Electrical connector |
| WO2001070675A2 (en) | 2000-03-24 | 2001-09-27 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| CA2408385A1 (en) * | 2000-03-24 | 2001-09-24 | Methylgene, Inc. | Inhibition of specific histone deacetylase isoforms |
| AU2001280167A1 (en) * | 2000-08-31 | 2002-03-13 | Wakunaga Pharmaceutical Co.,Ltd | Novel propenohydroxamic acid derivatives |
| PE20020354A1 (es) | 2000-09-01 | 2002-06-12 | Novartis Ag | Compuestos de hidroxamato como inhibidores de histona-desacetilasa (hda) |
| IL155196A0 (en) | 2000-10-05 | 2003-11-23 | Fujisawa Pharmaceutical Co | Benzamide derivatives and pharmaceutical compositions containing the same |
| SE0101386D0 (sv) | 2001-04-20 | 2001-04-20 | Astrazeneca Ab | New compounds |
| US6905669B2 (en) | 2001-04-24 | 2005-06-14 | Supergen, Inc. | Compositions and methods for reestablishing gene transcription through inhibition of DNA methylation and histone deacetylase |
| EE200400061A (et) | 2001-08-11 | 2004-04-15 | Bristol-Myers Squibb Pharma Company | Trifenüületüleeni derivaadid kui selektiivsed östrogeeniretseptori modulaatorid ja neid sisaldavad ravimkoostised |
| US6706686B2 (en) * | 2001-09-27 | 2004-03-16 | The Regents Of The University Of Colorado | Inhibition of histone deacetylase as a treatment for cardiac hypertrophy |
| DE10152764A1 (de) * | 2001-10-29 | 2003-05-08 | Linde Ag | Ventil für kryogene Medien |
-
2001
- 2001-08-28 PE PE2001000866A patent/PE20020354A1/es not_active Application Discontinuation
- 2001-08-30 SK SK242-2003A patent/SK287609B6/sk not_active IP Right Cessation
- 2001-08-30 PT PT01960717T patent/PT1318980E/pt unknown
- 2001-08-30 NZ NZ524365A patent/NZ524365A/en not_active IP Right Cessation
- 2001-08-30 MY MYPI20014079A patent/MY136892A/en unknown
- 2001-08-30 AR ARP010104140A patent/AR035057A1/es active IP Right Grant
- 2001-08-30 CZ CZ20030573A patent/CZ302707B6/cs not_active IP Right Cessation
- 2001-08-30 PL PL361408A patent/PL221738B1/pl unknown
- 2001-08-30 AU AU2001282129A patent/AU2001282129B2/en not_active Ceased
- 2001-08-30 IL IL15457401A patent/IL154574A0/xx unknown
- 2001-08-30 HU HU0300880A patent/HU229796B1/hu active Protection Beyond IP Right Term
- 2001-08-30 MX MXPA03001832A patent/MXPA03001832A/es active IP Right Grant
- 2001-08-30 CA CA2420899A patent/CA2420899C/en not_active Expired - Lifetime
- 2001-08-30 SI SI200130803T patent/SI1318980T1/sl unknown
- 2001-08-30 AT AT01960717T patent/ATE376999T1/de active
- 2001-08-30 BR BRPI0113669A patent/BRPI0113669B8/pt not_active IP Right Cessation
- 2001-08-30 AU AU8212901A patent/AU8212901A/xx active Pending
- 2001-08-30 RU RU2003108857A patent/RU2302408C3/ru not_active IP Right Cessation
- 2001-08-30 ES ES01960717T patent/ES2292610T3/es not_active Expired - Lifetime
- 2001-08-30 JP JP2002526830A patent/JP4012819B2/ja not_active Expired - Lifetime
- 2001-08-30 EP EP07115019A patent/EP1870399A1/en not_active Withdrawn
- 2001-08-30 EP EP01960717A patent/EP1318980B1/en not_active Expired - Lifetime
- 2001-08-30 CN CNB018150675A patent/CN1300110C/zh not_active Expired - Lifetime
- 2001-08-30 WO PCT/EP2001/010037 patent/WO2002022577A2/en not_active Ceased
- 2001-08-30 KR KR1020037002446A patent/KR100585484B1/ko not_active Expired - Fee Related
- 2001-08-30 DE DE60131179T patent/DE60131179T2/de not_active Expired - Lifetime
- 2001-08-30 DK DK01960717T patent/DK1318980T3/da active
- 2001-08-31 US US09/944,275 patent/US6552065B2/en not_active Expired - Lifetime
- 2001-08-31 TW TW090121617A patent/TWI286544B/zh not_active IP Right Cessation
-
2002
- 2002-11-19 US US10/299,518 patent/US6833384B2/en active Active
-
2003
- 2003-02-20 IL IL154574A patent/IL154574A/en active IP Right Grant
- 2003-02-21 ZA ZA200301423A patent/ZA200301423B/en unknown
- 2003-02-25 EC EC2003004492A patent/ECSP034492A/es unknown
- 2003-02-25 NO NO20030867A patent/NO324942B1/no not_active IP Right Cessation
-
2004
- 2004-11-09 US US10/984,501 patent/US7067551B2/en not_active Expired - Lifetime
-
2006
- 2006-04-20 US US11/408,129 patent/US20060189674A1/en not_active Abandoned
-
2007
- 2007-12-19 CY CY20071101619T patent/CY1107839T1/el unknown
-
2008
- 2008-03-11 US US12/045,885 patent/US20080176849A1/en not_active Abandoned
-
2015
- 2015-11-30 NL NL300778C patent/NL300778I2/nl unknown
- 2015-12-01 LU LU92890C patent/LU92890I2/xx unknown
- 2015-12-03 BE BE2015C062C patent/BE2015C062I2/fr unknown
- 2015-12-08 FR FR15C0086C patent/FR15C0086I2/fr active Active
- 2015-12-10 NO NO2015026C patent/NO2015026I2/no not_active IP Right Cessation
- 2015-12-14 CY CY2015053C patent/CY2015053I2/el unknown
- 2015-12-16 HU HUS1500068C patent/HUS1500068I1/hu unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NZ524365A (en) | Hydroxamate derivatives useful as deacetylase inhibitors | |
| AU2001282129A1 (en) | Hydroxamate derivatives useful as deacetylase inhibitors | |
| CN102656141B (zh) | 模拟造血生长因子的小分子化合物及其用途 | |
| EP3154982A1 (en) | Compounds comprising 1,1',2,5'-tetrahydrospiro[indole-3,2'-pyrrole]-2,5'-dione system as inhibitors p53-mdm2 protein-protein interaction | |
| CA2617636A1 (en) | Use of histone deacetylase inhibitors for treating cardiac hypertrophy and heart failure | |
| WO2015004610A1 (en) | 1,5-dihydropyrrol-2-one derivatives as inhibitors of p53-mdm2/mdm4 protein-protein interaction | |
| HK1057746B (en) | Hydroxamate derivatives useful as deacetylase inhibitors | |
| CN117304182A (zh) | 一类具有嘧啶并六元环结构的化合物、包含其的药物组合物及其应用 | |
| CN111548286B (zh) | 一种具有hdac3抑制活性的psa衍生物及其应用 | |
| CN110066236A (zh) | 1h-吡咯衍生物、其制备方法、药物组合物及应用 | |
| WO2025242233A1 (zh) | 一种酰胺吲嗪类化合物及其制备方法和应用 | |
| CA2533433A1 (en) | Novel n-substituted indolyl-3-glyoxylic acid amides, use thereof as a medicament, and method for the production thereof | |
| HK1122270A (en) | Novel fluorene derivatives, composition containing said derivatives and the use thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 7 YEARS UNTIL 30 AUG 2021 BY CPA GLOBAL Effective date: 20140717 |
|
| ASS | Change of ownership |
Owner name: SECURA BIO, INC., US Effective date: 20190827 |
|
| EXPY | Patent expired |