JP2008540574A - ヒストンデアセチラーゼ阻害剤 - Google Patents
ヒストンデアセチラーゼ阻害剤 Download PDFInfo
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- JP2008540574A JP2008540574A JP2008511453A JP2008511453A JP2008540574A JP 2008540574 A JP2008540574 A JP 2008540574A JP 2008511453 A JP2008511453 A JP 2008511453A JP 2008511453 A JP2008511453 A JP 2008511453A JP 2008540574 A JP2008540574 A JP 2008540574A
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- Prior art keywords
- alkyl
- hetero
- cycloalkyl
- bicycloaryl
- amino
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- 239000003276 histone deacetylase inhibitor Substances 0.000 title description 30
- 229940121372 histone deacetylase inhibitor Drugs 0.000 title description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 133
- 102000003964 Histone deacetylase Human genes 0.000 claims abstract description 58
- 108090000353 Histone deacetylase Proteins 0.000 claims abstract description 58
- 238000000034 method Methods 0.000 claims abstract description 37
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 1727
- 125000005842 heteroatom Chemical group 0.000 claims description 898
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 704
- -1 sulfone amide Chemical class 0.000 claims description 681
- 125000001072 heteroaryl group Chemical group 0.000 claims description 367
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 360
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 338
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 329
- 125000003118 aryl group Chemical group 0.000 claims description 220
- 229910052739 hydrogen Inorganic materials 0.000 claims description 181
- 239000001257 hydrogen Substances 0.000 claims description 181
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 174
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 172
- 125000003545 alkoxy group Chemical group 0.000 claims description 170
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 169
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 169
- 125000003282 alkyl amino group Chemical group 0.000 claims description 168
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 167
- 125000004104 aryloxy group Chemical group 0.000 claims description 163
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 157
- 150000002431 hydrogen Chemical class 0.000 claims description 85
- 125000005843 halogen group Chemical group 0.000 claims description 60
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 57
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 41
- 201000010099 disease Diseases 0.000 claims description 38
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 38
- 125000004429 atom Chemical group 0.000 claims description 34
- 229940124530 sulfonamide Drugs 0.000 claims description 30
- 150000003456 sulfonamides Chemical class 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 29
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 21
- 238000001727 in vivo Methods 0.000 claims description 18
- 125000005647 linker group Chemical group 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 230000007170 pathology Effects 0.000 claims description 15
- 230000002401 inhibitory effect Effects 0.000 claims description 13
- 206010028980 Neoplasm Diseases 0.000 claims description 12
- 201000011510 cancer Diseases 0.000 claims description 12
- 230000000694 effects Effects 0.000 claims description 12
- 150000001408 amides Chemical class 0.000 claims description 10
- 125000005549 heteroarylene group Chemical group 0.000 claims description 10
- 102100039999 Histone deacetylase 2 Human genes 0.000 claims description 9
- 102100038715 Histone deacetylase 8 Human genes 0.000 claims description 9
- 101001035011 Homo sapiens Histone deacetylase 2 Proteins 0.000 claims description 9
- 101001032118 Homo sapiens Histone deacetylase 8 Proteins 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000005022 packaging material Substances 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 4
- 238000003860 storage Methods 0.000 claims description 4
- 206010005003 Bladder cancer Diseases 0.000 claims description 2
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- 206010009944 Colon cancer Diseases 0.000 claims description 2
- 206010033128 Ovarian cancer Diseases 0.000 claims description 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 230000003463 hyperproliferative effect Effects 0.000 claims description 2
- 238000001361 intraarterial administration Methods 0.000 claims description 2
- 238000007918 intramuscular administration Methods 0.000 claims description 2
- 238000007912 intraperitoneal administration Methods 0.000 claims description 2
- 238000007913 intrathecal administration Methods 0.000 claims description 2
- 238000001990 intravenous administration Methods 0.000 claims description 2
- 239000002502 liposome Substances 0.000 claims description 2
- 201000001441 melanoma Diseases 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 208000017520 skin disease Diseases 0.000 claims description 2
- 206010041823 squamous cell carcinoma Diseases 0.000 claims description 2
- 238000007920 subcutaneous administration Methods 0.000 claims description 2
- 230000000699 topical effect Effects 0.000 claims description 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 57
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims 12
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 4
- 125000002541 furyl group Chemical group 0.000 claims 2
- 239000012669 liquid formulation Substances 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims 1
- FFBCUULSECUDSE-UHFFFAOYSA-N 2-[(1,1,3-trioxo-4h-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]-1,3-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=COC(CN2S(C3=CC=CC=C3NC2=O)(=O)=O)=N1 FFBCUULSECUDSE-UHFFFAOYSA-N 0.000 claims 1
- HCZJILWHQLGZMD-UHFFFAOYSA-N 2-[(1,1,3-trioxo-4h-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]-1,3-oxazole-5-carboxylic acid Chemical compound O1C(C(=O)O)=CN=C1CN1S(=O)(=O)C2=CC=CC=C2NC1=O HCZJILWHQLGZMD-UHFFFAOYSA-N 0.000 claims 1
- MFZGSEIKQHSGTI-UHFFFAOYSA-N 2-[(1,1,3-trioxo-4h-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC(CN2S(C3=CC=CC=C3NC2=O)(=O)=O)=N1 MFZGSEIKQHSGTI-UHFFFAOYSA-N 0.000 claims 1
- ZNDLSQUXFUFOFV-UHFFFAOYSA-N 2-[(1,1,3-trioxo-4h-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(=O)O)=CN=C1CN1S(=O)(=O)C2=CC=CC=C2NC1=O ZNDLSQUXFUFOFV-UHFFFAOYSA-N 0.000 claims 1
- GAXQCXYAFVRNCL-UHFFFAOYSA-N 4-[(3-amino-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]-n-(2-aminophenyl)benzamide Chemical compound NC1=NC2=CC=CC=C2S(=O)(=O)N1CC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N GAXQCXYAFVRNCL-UHFFFAOYSA-N 0.000 claims 1
- JQMIILCJCAIDET-UHFFFAOYSA-N 4-[(3-amino-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-4-yl)methyl]-n-(2-aminophenyl)benzamide Chemical compound NC1=NS(=O)(=O)C2=CC=CC=C2N1CC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N JQMIILCJCAIDET-UHFFFAOYSA-N 0.000 claims 1
- JOIOVVXGHGRDQK-UHFFFAOYSA-N 4-[[7-(2-aminoethoxy)-1,1,3-trioxo-4h-1$l^{6},2,4-benzothiadiazin-2-yl]methyl]-n-(2-aminophenyl)benzamide Chemical compound O=S1(=O)C2=CC(OCCN)=CC=C2NC(=O)N1CC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N JOIOVVXGHGRDQK-UHFFFAOYSA-N 0.000 claims 1
- RACAIXNNMWKXQL-UHFFFAOYSA-N 4-[[7-(2-aminoethylamino)-1,1,3-trioxo-4h-1$l^{6},2,4-benzothiadiazin-2-yl]methyl]-n-(2-aminophenyl)benzamide Chemical compound O=S1(=O)C2=CC(NCCN)=CC=C2NC(=O)N1CC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N RACAIXNNMWKXQL-UHFFFAOYSA-N 0.000 claims 1
- CCVPLOVTMNISED-UHFFFAOYSA-N 4-[[7-(2-aminoethylsulfanyl)-1,1,3-trioxo-4h-1$l^{6},2,4-benzothiadiazin-2-yl]methyl]-n-(2-aminophenyl)benzamide Chemical compound O=S1(=O)C2=CC(SCCN)=CC=C2NC(=O)N1CC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N CCVPLOVTMNISED-UHFFFAOYSA-N 0.000 claims 1
- SECICSOLRBGEOW-UHFFFAOYSA-N 5-[(1,1,3-trioxo-4h-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]furan-2-carboxylic acid Chemical compound O1C(C(=O)O)=CC=C1CN1S(=O)(=O)C2=CC=CC=C2NC1=O SECICSOLRBGEOW-UHFFFAOYSA-N 0.000 claims 1
- LOTJMCKPFSCZRB-UHFFFAOYSA-N 5-[(1,1,3-trioxo-4h-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1CN1S(=O)(=O)C2=CC=CC=C2NC1=O LOTJMCKPFSCZRB-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 206010003571 Astrocytoma Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- 206010017993 Gastrointestinal neoplasms Diseases 0.000 claims 1
- 208000032612 Glial tumor Diseases 0.000 claims 1
- 206010018338 Glioma Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000007766 Kaposi sarcoma Diseases 0.000 claims 1
- 206010041067 Small cell lung cancer Diseases 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 208000008385 Urogenital Neoplasms Diseases 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- 201000010536 head and neck cancer Diseases 0.000 claims 1
- 208000014829 head and neck neoplasm Diseases 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- ZUZQYYBHXGKXEP-UHFFFAOYSA-N n-(2-amino-5-fluorophenyl)-4-[(1,1,3-trioxo-4h-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]benzamide Chemical compound NC1=CC=C(F)C=C1NC(=O)C(C=C1)=CC=C1CN1S(=O)(=O)C2=CC=CC=C2NC1=O ZUZQYYBHXGKXEP-UHFFFAOYSA-N 0.000 claims 1
- HCWUKZIVAINRQU-UHFFFAOYSA-N n-(2-amino-5-fluorophenyl)-4-[(6-methoxy-1,1-dioxo-3-sulfanylidene-4h-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]benzamide Chemical compound C=1C(OC)=CC=C(S2(=O)=O)C=1NC(=S)N2CC(C=C1)=CC=C1C(=O)NC1=CC(F)=CC=C1N HCWUKZIVAINRQU-UHFFFAOYSA-N 0.000 claims 1
- NPQDLOHJMQJGSD-UHFFFAOYSA-N n-(2-amino-5-morpholin-4-ylphenyl)-4-[(1,1,3-trioxo-4h-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]benzamide Chemical compound C1=C(NC(=O)C=2C=CC(CN3S(C4=CC=CC=C4NC3=O)(=O)=O)=CC=2)C(N)=CC=C1N1CCOCC1 NPQDLOHJMQJGSD-UHFFFAOYSA-N 0.000 claims 1
- SYIAJYHJBLEYLI-UHFFFAOYSA-N n-(2-amino-5-phenylphenyl)-4-[(1,1,3-trioxo-4h-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]benzamide Chemical compound C1=C(NC(=O)C=2C=CC(CN3S(C4=CC=CC=C4NC3=O)(=O)=O)=CC=2)C(N)=CC=C1C1=CC=CC=C1 SYIAJYHJBLEYLI-UHFFFAOYSA-N 0.000 claims 1
- JMDWFDLZJZTRLR-UHFFFAOYSA-N n-(2-amino-5-thiomorpholin-4-ylphenyl)-4-[(1,1,3-trioxo-4h-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]benzamide Chemical compound C1=C(NC(=O)C=2C=CC(CN3S(C4=CC=CC=C4NC3=O)(=O)=O)=CC=2)C(N)=CC=C1N1CCSCC1 JMDWFDLZJZTRLR-UHFFFAOYSA-N 0.000 claims 1
- SOTLMITVZGHQAC-UHFFFAOYSA-N n-(2-aminophenyl)-1-methyl-2-[(1,1,3-trioxo-4h-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]imidazole-4-carboxamide Chemical compound N1=C(CN2S(C3=CC=CC=C3NC2=O)(=O)=O)N(C)C=C1C(=O)NC1=CC=CC=C1N SOTLMITVZGHQAC-UHFFFAOYSA-N 0.000 claims 1
- HAFONOYZGYJGEX-UHFFFAOYSA-N n-(2-aminophenyl)-1-methyl-5-[(1,1,3-trioxo-4h-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]pyrrole-2-carboxamide Chemical compound CN1C(CN2S(C3=CC=CC=C3NC2=O)(=O)=O)=CC=C1C(=O)NC1=CC=CC=C1N HAFONOYZGYJGEX-UHFFFAOYSA-N 0.000 claims 1
- GGVHOWJRPMWSNE-UHFFFAOYSA-N n-(2-aminophenyl)-3-fluoro-4-[(1,1,3-trioxo-4h-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1F)=CC=C1CN1S(=O)(=O)C2=CC=CC=C2NC1=O GGVHOWJRPMWSNE-UHFFFAOYSA-N 0.000 claims 1
- ICORXRWLUDPJNJ-UHFFFAOYSA-N n-(2-aminophenyl)-3-methyl-2-[(1,1,3-trioxo-4h-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]imidazole-4-carboxamide Chemical compound CN1C(CN2S(C3=CC=CC=C3NC2=O)(=O)=O)=NC=C1C(=O)NC1=CC=CC=C1N ICORXRWLUDPJNJ-UHFFFAOYSA-N 0.000 claims 1
- IGNFSQWGYYCBAW-UHFFFAOYSA-N n-(2-aminophenyl)-4-[(1,1,3-trioxo-4h-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1CN1S(=O)(=O)C2=CC=CC=C2NC1=O IGNFSQWGYYCBAW-UHFFFAOYSA-N 0.000 claims 1
- OURMGAFSPQQEME-UHFFFAOYSA-N n-(2-aminophenyl)-4-[(1,1,3-trioxo-4h-pyrido[4,3-e][1,2,4]thiadiazin-2-yl)methyl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1CN1S(=O)(=O)C2=CN=CC=C2NC1=O OURMGAFSPQQEME-UHFFFAOYSA-N 0.000 claims 1
- SPUREBYFGQJFAJ-UHFFFAOYSA-N n-(2-aminophenyl)-4-[(1,1,3-trioxo-7-pyridin-3-yl-4h-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1CN1S(=O)(=O)C2=CC(C=3C=NC=CC=3)=CC=C2NC1=O SPUREBYFGQJFAJ-UHFFFAOYSA-N 0.000 claims 1
- CSUUEZKUXNGQKQ-UHFFFAOYSA-N n-(2-aminophenyl)-4-[(1,1,3-trioxo-7-pyridin-4-yl-4h-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1CN1S(=O)(=O)C2=CC(C=3C=CN=CC=3)=CC=C2NC1=O CSUUEZKUXNGQKQ-UHFFFAOYSA-N 0.000 claims 1
- KQRSYOYCZXMAOA-UHFFFAOYSA-N n-(2-aminophenyl)-4-[(1,1,3-trioxo-7-pyrimidin-5-yl-4h-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1CN1S(=O)(=O)C2=CC(C=3C=NC=NC=3)=CC=C2NC1=O KQRSYOYCZXMAOA-UHFFFAOYSA-N 0.000 claims 1
- XMZALHPBKARPRB-UHFFFAOYSA-N n-(2-aminophenyl)-4-[(1,1,3-trioxo-7-thiophen-2-yl-4h-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1CN1S(=O)(=O)C2=CC(C=3SC=CC=3)=CC=C2NC1=O XMZALHPBKARPRB-UHFFFAOYSA-N 0.000 claims 1
- WQACHYDHMOHTFB-UHFFFAOYSA-N n-(2-aminophenyl)-4-[(1,1,3-trioxo-7-thiophen-3-yl-4h-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1CN1S(=O)(=O)C2=CC(C3=CSC=C3)=CC=C2NC1=O WQACHYDHMOHTFB-UHFFFAOYSA-N 0.000 claims 1
- YSFQTZRFPWSZHQ-UHFFFAOYSA-N n-(2-aminophenyl)-4-[(1,1-dioxo-3-sulfanylidene-4h-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1CN1S(=O)(=O)C2=CC=CC=C2NC1=S YSFQTZRFPWSZHQ-UHFFFAOYSA-N 0.000 claims 1
- WSFPYKBIVXZFKA-UHFFFAOYSA-N n-(2-aminophenyl)-4-[(3-ethylsulfanyl-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]benzamide Chemical compound CCSC1=NC2=CC=CC=C2S(=O)(=O)N1CC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N WSFPYKBIVXZFKA-UHFFFAOYSA-N 0.000 claims 1
- JOCMGYOZTSCQSH-UHFFFAOYSA-N n-(2-aminophenyl)-4-[(3-methyl-2-oxo-4h-quinazolin-1-yl)methyl]benzamide Chemical compound O=C1N(C)CC2=CC=CC=C2N1CC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N JOCMGYOZTSCQSH-UHFFFAOYSA-N 0.000 claims 1
- JFHIAIDFNFNQEE-UHFFFAOYSA-N n-(2-aminophenyl)-4-[(3-methyl-2-sulfanylidene-4h-quinazolin-1-yl)methyl]benzamide Chemical compound S=C1N(C)CC2=CC=CC=C2N1CC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N JFHIAIDFNFNQEE-UHFFFAOYSA-N 0.000 claims 1
- UPRMJMMHAQDMAI-UHFFFAOYSA-N n-(2-aminophenyl)-4-[(3-methylsulfanyl-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]benzamide Chemical compound CSC1=NC2=CC=CC=C2S(=O)(=O)N1CC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N UPRMJMMHAQDMAI-UHFFFAOYSA-N 0.000 claims 1
- YVPPDNSLVOZJFE-UHFFFAOYSA-N n-(2-aminophenyl)-4-[(6-fluoro-1,1-dioxo-3-sulfanylidene-4h-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1CN1S(=O)(=O)C2=CC=C(F)C=C2NC1=S YVPPDNSLVOZJFE-UHFFFAOYSA-N 0.000 claims 1
- IDDIZVJTAKSTIQ-UHFFFAOYSA-N n-(2-aminophenyl)-4-[(6-methoxy-1,1-dioxo-3-sulfanylidene-4h-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]benzamide Chemical compound C=1C(OC)=CC=C(S2(=O)=O)C=1NC(=S)N2CC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N IDDIZVJTAKSTIQ-UHFFFAOYSA-N 0.000 claims 1
- DTMURQYPPAHUAF-UHFFFAOYSA-N n-(2-aminophenyl)-4-[(6-methoxy-3-methylsulfanyl-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-2-yl)methyl]benzamide Chemical compound C=1C(OC)=CC=C(S2(=O)=O)C=1N=C(SC)N2CC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N DTMURQYPPAHUAF-UHFFFAOYSA-N 0.000 claims 1
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- C07D285/15—Six-membered rings
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- C07D285/18—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines
- C07D285/20—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems
- C07D285/22—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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| JP2012510512A (ja) * | 2008-12-03 | 2012-05-10 | マサチューセッツ インスティテュート オブ テクノロジー | 記憶を推進するためのｈｄａｃ２の阻害 |
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Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2465978C (en) | 2001-09-14 | 2015-04-07 | Soon Hyung Woo | Inhibitors of histone deacetylase |
| US6897220B2 (en) | 2001-09-14 | 2005-05-24 | Methylgene, Inc. | Inhibitors of histone deacetylase |
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| EP1824831A2 (en) | 2004-12-16 | 2007-08-29 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
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| TW200911757A (en) * | 2007-01-18 | 2009-03-16 | Takeda San Diego Inc | Crystalline forms of histone deacetylase inhibitors |
| US8030344B2 (en) | 2007-03-13 | 2011-10-04 | Methylgene Inc. | Inhibitors of histone deacetylase |
| CN103087043A (zh) * | 2007-03-16 | 2013-05-08 | 中国人民解放军军事医学科学院放射与辐射医学研究所 | 具有抗增殖活性的苯甲酰胺类衍生物及其药用制剂 |
| AU2008338631A1 (en) * | 2007-12-14 | 2009-06-25 | Georgetown University | Histone deacetylase inhibitors |
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| ES2620027T3 (es) | 2008-09-03 | 2017-06-27 | Biomarin Pharmaceutical Inc. | Composiciones que incluyen derivados del ácido 6-aminohexanoico como inhibidores de HDAC |
| TW201118081A (en) * | 2009-10-07 | 2011-06-01 | Siena Biotech Spa | Wnt pathway antagonists |
| CN102584741A (zh) * | 2011-01-06 | 2012-07-18 | 中国科学院上海药物研究所 | 酰胺类化合物及其制备方法、组合物和用途 |
| US10059723B2 (en) | 2011-02-28 | 2018-08-28 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
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| ES2719266T3 (es) | 2011-07-22 | 2019-07-09 | Massachusetts Inst Technology | Activadores de histona desacetilasas de clase I (HDACS), y usos de los mismos |
| KR20150132345A (ko) | 2013-03-15 | 2015-11-25 | 바이오마린 파머수티컬 인크. | Hdac 저해제 |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003024448A2 (en) * | 2001-09-14 | 2003-03-27 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| JP2003137866A (ja) * | 2001-11-01 | 2003-05-14 | Sankyo Co Ltd | フェニレンジアミン誘導体 |
Family Cites Families (326)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4482571A (en) | 1982-06-21 | 1984-11-13 | University Of Pittsburgh | Sickle cell anemia treatment and compound |
| GB8524157D0 (en) | 1984-10-19 | 1985-11-06 | Ici America Inc | Heterocyclic amides |
| GB8607294D0 (en) | 1985-04-17 | 1986-04-30 | Ici America Inc | Heterocyclic amide derivatives |
| EP0227241B1 (en) | 1985-10-17 | 1996-09-11 | Zeneca Inc. | Medicinal indole and indazole keto sulphone derivatives |
| US4964895A (en) | 1987-06-08 | 1990-10-23 | Monsanto Company | Substituted 4-(4-nitrophenoxy) pyrazoles and their use as herbicides |
| US4997815A (en) | 1988-11-01 | 1991-03-05 | Children's Hospital Medical Center Of Northern California | Method for augmenting fetal hemoglobin by treatment with activin and/or inhibin |
| CA2046628A1 (en) | 1989-02-08 | 1990-08-09 | Dee W. Brooks | 4-hydroxythiazoles as 5-lipoxygenase inhibitors |
| US5216004A (en) | 1990-09-13 | 1993-06-01 | Children's Hospital Medical Center Of North California | Method for preventing malaria |
| US5656644A (en) | 1994-07-20 | 1997-08-12 | Smithkline Beecham Corporation | Pyridyl imidazoles |
| US5439939A (en) | 1992-03-17 | 1995-08-08 | Children's Hospital Medical Center Of Northern California | Pharmaceutical compositions and methods using isobutyramide for treating betaglobin disorders |
| AU696167B2 (en) | 1993-10-29 | 1998-09-03 | Trustees Of Boston University | Physiologically stable compositions of butyric acid, and butyric acid salts and derivatives as anti-neoplastic agents |
| CA2175249A1 (en) | 1993-11-10 | 1995-05-18 | Harold L. Newmark | Butyric ester cyto-differentiating agents |
| US5569675A (en) | 1994-03-07 | 1996-10-29 | Bar Ilan University | Methods of using carboxylic acid esters to increase fetal-hemoglobin levels |
| US6071923A (en) | 1994-09-16 | 2000-06-06 | Bar-Ilan University | Retinoyloxy aryl-substituted alkylene butyrates useful for the treatment of cancer and other proliferative diseases |
| US6040342A (en) | 1994-09-16 | 2000-03-21 | Bar-Ilan University | Retinoyloxy (alkyl-substituted) methyl butyrates useful for the treatment of cancer and other proliferative diseases |
| US5789434A (en) | 1994-11-15 | 1998-08-04 | Bayer Corporation | Derivatives of substituted 4-biarylbutyric acid as matrix metalloprotease inhibitors |
| US6011000A (en) | 1995-03-03 | 2000-01-04 | Perrine; Susan P. | Compositions for the treatment of blood disorders |
| US5700826A (en) | 1995-06-07 | 1997-12-23 | Ontogen Corporation | 1,2,4,5-tetra substituted imidazoles as modulators of multi-drug resistance |
| JP3964478B2 (ja) | 1995-06-30 | 2007-08-22 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ヘテロ環含有カルボン酸誘導体及びそれを含有する医薬 |
| US5922837A (en) | 1995-09-20 | 1999-07-13 | Merck & Co., Inc. | Antiprotozoal cyclic tetrapeptides |
| US6110697A (en) | 1995-09-20 | 2000-08-29 | Merck & Co., Inc. | Histone deacetylase as target for antiprotozoal agents |
| EP0855024A4 (en) | 1995-09-20 | 2001-08-22 | Merck & Co Inc | HISTONE DEACETYLASE AS THE ATTACK POINT FOR ANTIPROTOZOIC ACTIVE SUBSTANCES |
| US20030219832A1 (en) | 1996-03-11 | 2003-11-27 | Klein Elliott S. | Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities |
| US6777217B1 (en) | 1996-03-26 | 2004-08-17 | President And Fellows Of Harvard College | Histone deacetylases, and uses related thereto |
| WO1997047307A1 (en) | 1996-06-14 | 1997-12-18 | The Uab Research Foundation | Use of histone deacetylase inhibitors to activate transgene expression |
| JP2002514161A (ja) | 1996-07-02 | 2002-05-14 | バー イラン ユニバーシティー | ガンおよび他の細胞増殖性疾患の治療に有用なレチノイルオキシ（置換）アルキレンブチレート |
| US6197743B1 (en) | 1996-07-26 | 2001-03-06 | The Trustees Of Boston University | Compositions and methods for the treatment of viral disorders |
| US5939456A (en) | 1996-07-26 | 1999-08-17 | Perrine; Susan P. | Pulsed administration of compositions for the treatment of blood disorders |
| EP0827742A1 (en) | 1996-09-04 | 1998-03-11 | Vrije Universiteit Brussel | Use of histone deacetylase inhibitors for treating fribosis or cirrhosis |
| US6068987A (en) | 1996-09-20 | 2000-05-30 | Merck & Co., Inc. | Histone deacetylase as target for antiprotozoal agents |
| US6794392B1 (en) | 1996-09-30 | 2004-09-21 | Schering Aktiengesellschaft | Cell differentiation inducer |
| US6174905B1 (en) | 1996-09-30 | 2001-01-16 | Mitsui Chemicals, Inc. | Cell differentiation inducer |
| EP0946508B1 (en) | 1996-12-23 | 2009-09-23 | Bristol-Myers Squibb Pharma Company | NITROGEN CONTAINING HETEROAROMATICS AS FACTOR Xa INHIBITORS |
| EP0961614A4 (en) | 1996-12-30 | 2002-07-24 | Univ Bar Ilan | OXYALKYLESTERS CONTAINING AND USING THE TRICARBOXYL ACIDS |
| US6235474B1 (en) | 1996-12-30 | 2001-05-22 | The Johns Hopkins University | Methods and kits for diagnosing and determination of the predisposition for diseases |
| US6130248A (en) | 1996-12-30 | 2000-10-10 | Bar-Ilan University | Tricarboxylic acid-containing oxyalkyl esters and uses thereof |
| US7062219B2 (en) | 1997-01-31 | 2006-06-13 | Odyssey Thera Inc. | Protein fragment complementation assays for high-throughput and high-content screening |
| US5939455A (en) | 1997-03-11 | 1999-08-17 | Beacon Laboratories, Inc. | Therapeutic augmentation of oxyalkylene diesters and butyric acid derivatives |
| US6124495A (en) | 1997-03-11 | 2000-09-26 | Beacon Laboratories, Inc. | Unsaturated oxyalkylene esters and uses thereof |
| US6110955A (en) | 1997-03-11 | 2000-08-29 | Beacon Laboratories, Inc. | Metabolically stabilized oxyalkylene esters and uses thereof |
| US6110970A (en) | 1997-03-11 | 2000-08-29 | Beacon Laboratories, Inc. | Nitrogen-containing oxyalkylene esters and uses thereof |
| US6043389A (en) | 1997-03-11 | 2000-03-28 | Mor Research Applications, Ltd. | Hydroxy and ether-containing oxyalkylene esters and uses thereof |
| US6030961A (en) | 1997-03-11 | 2000-02-29 | Bar-Ilan Research & Development Co., Ltd. | Oxyalkylene phosphate compounds and uses thereof |
| US6387673B1 (en) | 1997-05-01 | 2002-05-14 | The Salk Institute For Biological Studies | Compounds useful for the modulation of processes mediated by nuclear hormone receptors, methods for the identification and use of such compounds |
| US6231880B1 (en) | 1997-05-30 | 2001-05-15 | Susan P. Perrine | Compositions and administration of compositions for the treatment of blood disorders |
| AUPO721997A0 (en) | 1997-06-06 | 1997-07-03 | Queensland Institute Of Medical Research, The | Anticancer compounds |
| AUPO864097A0 (en) | 1997-08-19 | 1997-09-11 | Peplin Pty Ltd | Anti-cancer compounds |
| KR20010023449A (ko) | 1997-09-02 | 2001-03-26 | 나가시마 카쭈시게, 노미야마 아키히코 | 신규한 환상 테트라펩티드 유도체 및 그 의약 용도 |
| WO1999023885A1 (en) | 1997-11-10 | 1999-05-20 | The Salk Institute For Biological Studies | Methods for the use of inhibitors of co-repressors for the treatment of neoplastic diseases |
| US6884597B1 (en) | 1998-01-20 | 2005-04-26 | Medical & Biological Laboratories, Co., Ltd. | Method for detecting acetyltransferase and deacetylase activities and method for screening inhibitors or enhancers of these enzymes |
| US6262116B1 (en) | 1998-01-23 | 2001-07-17 | Sloan-Kettering Institute For Cancer Research | Transcription therapy for cancers |
| CA2324426A1 (en) | 1998-02-11 | 1999-08-19 | Douglas V. Faller | Compositions and methods for the treatment of cystic fibrosis |
| US6287843B1 (en) | 1998-04-03 | 2001-09-11 | Pioneer Hi-Bred International, Inc. | Maize histone deacetylases and their use |
| US6288063B1 (en) | 1998-05-27 | 2001-09-11 | Bayer Corporation | Substituted 4-biarylbutyric and 5-biarylpentanoic acid derivatives as matrix metalloprotease inhibitors |
| US20030236204A1 (en) | 2002-06-14 | 2003-12-25 | Isis Pharmaceuticals Inc. | Antisense modulation of histone deacetylase 2 expression |
| AUPP505798A0 (en) | 1998-08-04 | 1998-08-27 | Fujisawa Pharmaceutical Co., Ltd. | Novel compound fr225497 substance |
| JP2002523029A (ja) | 1998-08-21 | 2002-07-30 | スミスクライン ビーチャム コーポレーション | ヒトヒストンデアセチラーゼ遺伝子ｈｄ４ |
| DE19842506A1 (de) | 1998-09-17 | 2000-03-23 | Volkswagen Ag | Verfahren und Vorrichtung zur Überwachung von Signalen bei vernetzten Systemen |
| JP2002527449A (ja) | 1998-10-13 | 2002-08-27 | 藤沢薬品工業株式会社 | 環状テトラペプチド化合物およびその用途 |
| AU6339399A (en) | 1998-10-16 | 2000-05-08 | Novartis Ag | Promotion of self-renewal and improved gene transduction of hematopoietic stem cells by histone deacetylase inhibitors |
| CA2350086A1 (en) | 1998-11-10 | 2000-05-18 | Board Of Regents, The University Of Texas System | Methods for preventing cardiac hypertrophy and heart failure by inhibition of mef2 transcription factor |
| US6287790B1 (en) | 1998-11-30 | 2001-09-11 | The Regents Of The University Of California | Utilization of nuclear structural proteins for targeted therapy and detection of proliferative and differentiation disorders |
| US6335170B1 (en) | 1999-02-22 | 2002-01-01 | Torben F. Orntoft | Gene expression in bladder tumors |
| JP4269041B2 (ja) | 1999-03-02 | 2009-05-27 | 国立大学法人九州工業大学 | 新規な環状テトラペプチド誘導体とその医薬用途 |
| EP1164198B1 (en) | 1999-03-23 | 2006-06-07 | Chugai Seiyaku Kabushiki Kaisha | Method for screening anticancer agent |
| US6518012B1 (en) | 1999-04-02 | 2003-02-11 | Health Research, Inc. | Method for regulating the expression of MHC antigens and CD40 by inhibitors of histone deacetylation |
| DE60001229T2 (de) | 1999-04-09 | 2003-10-30 | Smithkline Beecham Corp., Philadelphia | Triarylimidazole |
| US20030078216A1 (en) | 1999-05-03 | 2003-04-24 | Macleod A. Robert | Inhibition of histone deactylase |
| JP2003500052A (ja) | 1999-05-03 | 2003-01-07 | メチルジーン インコーポレイテッド | ヒストン脱アセチル酵素の抑制 |
| US20030078369A1 (en) | 1999-07-23 | 2003-04-24 | Meinke Peter T. | Apicidin-derived cyclic tetrapeptides |
| EP1204411A1 (en) | 1999-07-23 | 2002-05-15 | Merck & Co., Inc. | Apicidin-derived cyclic tetrapeptides |
| WO2001014581A2 (en) | 1999-08-20 | 2001-03-01 | Board Of Regents, The University Of Texas System | Hdac4 and hdac5 in the regulation of cardiac gene expression |
| JP2001081031A (ja) | 1999-08-30 | 2001-03-27 | Schering Ag | 溶解性および経口吸収性を改善したベンズアミド誘導体含有製剤 |
| WO2001017514A1 (en) | 1999-09-03 | 2001-03-15 | The Salk Institute For Biological Studies | Modulation of gene expression by modulating histone acetylation |
| US6511990B1 (en) | 1999-09-08 | 2003-01-28 | Sloan-Kettering Institute For Cancer Research | Class of cytodifferentiating agents and histone deacetylase inhibitors, and methods of use thereof |
| DE60034688T2 (de) | 1999-09-08 | 2008-01-17 | Sloan-Kettering Institute For Cancer Research | Kristallstruktur einer deacetylase und deren inhibitoren |
| JP2003511054A (ja) | 1999-10-08 | 2003-03-25 | メルク エンド カムパニー インコーポレーテッド | 抗原虫ヒストンアセチルトランスフェラーゼインヒビター |
| US6541661B1 (en) | 1999-11-23 | 2003-04-01 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| JP2001149081A (ja) | 1999-11-29 | 2001-06-05 | Cyclex Co Ltd | 脱アセチル化酵素の活性測定方法、並びにこれら酵素の阻害剤もしくは促進剤のスクリーニング方法 |
| CA2291367A1 (en) | 1999-12-06 | 2001-06-06 | Isabelle Henry | Genetic constructions having a reduced or an increased number of epigenetic control regions and methods of use thereof |
| US6875598B1 (en) | 1999-12-08 | 2005-04-05 | Applera Corporation | Histone deacetylase-8 proteins, nuclei acids, and methods for use |
| ES2347284T3 (es) | 1999-12-08 | 2010-10-27 | Cyclacel Pharmaceuticals, Inc. | Uso de depsipeptido y congeneres del mismo como inmunosupresores en la prevencion o tratamiento del rechazo que sigue a un transplante y para inducir la apoptosis de celulas t cd4 o cd8 activadas. |
| WO2001042437A2 (en) | 1999-12-08 | 2001-06-14 | Axys Pharmaceuticals, Inc. | Histone deacetylase-8 proteins, nucleic acids, and methods of use |
| US6828302B1 (en) | 1999-12-08 | 2004-12-07 | Xcyte Therapies, Inc. | Therapeutic uses of depsipeptides and congeners thereof |
| US7452664B2 (en) | 1999-12-15 | 2008-11-18 | Massachusetts Institute Of Technology | Methods for identifying agents which alter histone protein acetylation |
| US6544957B2 (en) | 2000-01-04 | 2003-04-08 | The Johns Hopkins University | Methods and reagents for facilitating transcription |
| JP5047437B2 (ja) | 2000-02-08 | 2012-10-10 | サンガモ バイオサイエンシーズ， インコーポレイテッド | 薬物の発見のための細胞 |
| CA2401778C (en) | 2000-02-29 | 2010-12-21 | Cor Therapeutics, Inc. | Benzamides and related inhibitors of factor xa |
| US20030129724A1 (en) | 2000-03-03 | 2003-07-10 | Grozinger Christina M. | Class II human histone deacetylases, and uses related thereto |
| GB0005199D0 (en) | 2000-03-04 | 2000-04-26 | Imp College Innovations Ltd | Modulation of histone deacetylase |
| ATE489360T1 (de) | 2000-03-24 | 2010-12-15 | Methylgene Inc | Inhibitoren der histon-deacetylase |
| WO2003006652A2 (en) | 2000-03-24 | 2003-01-23 | Methylgene, Inc. | Inhibition of specific histone deacetylase isoforms |
| GB0007217D0 (en) | 2000-03-24 | 2000-05-17 | Europ I Of Oncology | Materials and methods relating to the treatment of leukaemias |
| US20020137162A1 (en) | 2000-03-24 | 2002-09-26 | Zuomei Li | Antisense oligonucleotide inhibition of specific histone deacetylase isoforms |
| EP1268534A2 (en) | 2000-03-24 | 2003-01-02 | Filgen Biosciences, Inc. | Peptides binding to non-acetylated h3 and h4 histones for cancer therapy |
| GB0007405D0 (en) | 2000-03-27 | 2000-05-17 | Smithkline Beecham Corp | Compounds |
| US6458589B1 (en) | 2000-04-27 | 2002-10-01 | Geron Corporation | Hepatocyte lineage cells derived from pluripotent stem cells |
| EP1170008A1 (en) | 2000-07-07 | 2002-01-09 | Chemotherapeutisches Forschungsinstitut Georg-Speyer-Haus | Valproic acid and derivatives thereof as histone deacetylase inhibitors |
| ES2321584T3 (es) | 2000-07-17 | 2009-06-09 | Astellas Pharma Inc. | Fk228 reducido y su uso. |
| US20020164752A1 (en) | 2000-07-21 | 2002-11-07 | Meyers Rachel A. | 47508, a novel human histone deacetylase family member and uses thereof |
| EP1310485A4 (en) | 2000-07-28 | 2005-07-20 | Sumitomo Pharma | pyrrole |
| US6673587B1 (en) | 2000-08-11 | 2004-01-06 | The Salk Institute For Biological Studies | Histone deacetylase, and uses therefor |
| EP1182263A1 (en) | 2000-08-11 | 2002-02-27 | Evotec OAI AG | Process for detecting threonine/serine kinase activity |
| AU2001285042A1 (en) | 2000-08-18 | 2002-03-04 | The Governement Of The United States Of America, Represented By The Secretary, Department Of Health And Human Services | Methods of treating cutaneous and peripheral t-cell lymphoma by a histone deacetylase inhibitor |
| PE20020354A1 (es) | 2000-09-01 | 2002-06-12 | Novartis Ag | Compuestos de hidroxamato como inhibidores de histona-desacetilasa (hda) |
| US20050004007A1 (en) | 2000-09-12 | 2005-01-06 | Steven Grant | Promotion of adoptosis in cancer cells by co-administration of cyclin dependent kinase inhibitiors and cellular differentiation agents |
| US6538030B2 (en) | 2000-09-20 | 2003-03-25 | Yih-Lin Chung | Treating radiation fibrosis |
| WO2002030879A2 (en) | 2000-09-29 | 2002-04-18 | Prolifix Limited | Carbamic acid compounds comprising a sulfonamide linkage as hdac inhibitors |
| GB0023983D0 (en) | 2000-09-29 | 2000-11-15 | Prolifix Ltd | Therapeutic compounds |
| EP2083005A1 (en) | 2000-09-29 | 2009-07-29 | TopoTarget UK Limited | Carbamic acid compounds comprising an amide linkage as HDAC inhibitors |
| AU2002215018A1 (en) | 2000-10-13 | 2002-04-22 | Bayer Aktiengesellschaft | Human histone deacetylase gene |
| DE10053474A1 (de) | 2000-10-24 | 2002-05-02 | Schering Ag | Schwefelhaltige Indirubinderivate, deren Herstellung und Verwendung |
| US20020103192A1 (en) | 2000-10-26 | 2002-08-01 | Curtin Michael L. | Inhibitors of histone deacetylase |
| WO2002036783A2 (en) | 2000-10-31 | 2002-05-10 | Bayer Aktiengesellschaft | Regulation of human histone deacetylase |
| US7439359B2 (en) | 2000-11-02 | 2008-10-21 | Sloan-Kettering Institute For Cancer Research | Small molecule compositions for binding to hsp90 |
| WO2002055017A2 (en) | 2000-11-21 | 2002-07-18 | Wake Forest University | Method of treating autoimmune diseases |
| DE10061162A1 (de) | 2000-11-30 | 2002-07-11 | Schering Ag | Aryl-substituierte Indirubinderivate, deren Herstellung und Verwendung |
| AR035659A1 (es) | 2000-12-07 | 2004-06-23 | Hoffmann La Roche | Hidroxiamidas de acido (1-oxo-1,2,3,4-tetrahidro-naftalen-2-il)-alcanoico, proceso para la manufactura de estos compuestos, composiciones farmaceuticas que contienen dichos compuestos y los usos de los mismos |
| US6376508B1 (en) | 2000-12-13 | 2002-04-23 | Academia Sinica | Treatments for spinal muscular atrophy |
| US20040005574A1 (en) | 2002-07-08 | 2004-01-08 | Leonard Guarente | SIR2 activity |
| WO2002048310A2 (en) | 2000-12-15 | 2002-06-20 | Genetics Institute, Llc | Methods and compositions for diagnosing and treating rheumatoid arthritis |
| US20050171042A1 (en) | 2000-12-19 | 2005-08-04 | Monia Brett P. | Compositions and their uses directed to binding proteins |
| US20040204373A1 (en) | 2000-12-19 | 2004-10-14 | Isis Pharmaceuticals Inc. | Antisense modulation of histone deacetylase I expression |
| WO2002050285A2 (en) | 2000-12-20 | 2002-06-27 | Novartis Ag | Histone deacetylase-related gene and protein |
| US6693132B2 (en) | 2000-12-21 | 2004-02-17 | Beacon Laboratories, Inc. | Methods for using alkanoyloxymethyl esters |
| US6562995B1 (en) | 2000-12-21 | 2003-05-13 | Beacon Laboratories, Inc. | Delta dicarbonyl compounds and methods for using the same |
| US6720445B2 (en) | 2000-12-21 | 2004-04-13 | Beacon Laboratories, Inc. | Acetyloxymethyl esters and methods for using the same |
| JP2004516328A (ja) | 2000-12-22 | 2004-06-03 | ヒャン ウー リー | アピシジン誘導体、その合成方法、及び該誘導体を含む抗癌剤組成物 |
| AR035513A1 (es) | 2000-12-23 | 2004-06-02 | Hoffmann La Roche | Derivados de tetrahidropiridina, proceso para prepararlos, composiciones farmaceuticas que los contienen, y uso de dichos compuestos en la preparacion de medicamentos |
| AU2002249938B2 (en) | 2001-01-10 | 2006-12-21 | The Government Of The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Histone deacetylase inhibitors in diagnosis and treatment of thyroid neoplasms |
| US20030148970A1 (en) | 2001-01-12 | 2003-08-07 | Besterman Jeffrey M. | Methods for specifically inhibiting histone deacetylase-4 |
| KR20040018328A (ko) | 2001-01-12 | 2004-03-03 | 메틸진, 인크. | 히스톤 디아세틸라제-4를 특이적으로 억제하는 방법 |
| US20030152557A1 (en) | 2001-01-12 | 2003-08-14 | Besterman Jeffrey M. | Methods for inhibiting histone deacetylase-4 |
| US6756200B2 (en) | 2001-01-26 | 2004-06-29 | The Johns Hopkins University School Of Medicine | Aberrantly methylated genes as markers of breast malignancy |
| AR035417A1 (es) | 2001-01-27 | 2004-05-26 | Hoffmann La Roche | Derivados triciclicos de lactama y sultama, procesos para su elaboracion, medicamentos que los contienen, y el uso de dichos compuestos en la preparacion de medicamentos |
| US20020183388A1 (en) | 2001-02-01 | 2002-12-05 | Gudas Lorraine J. | Use of retinoids plus histone deacetylase inhibitors to inhibit the growth of solid tumors |
| US20040091967A1 (en) | 2001-02-05 | 2004-05-13 | Kohler Ranier H | Regulation of human histone acetyltranseferase |
| US20020177594A1 (en) | 2001-03-14 | 2002-11-28 | Curtin Michael L. | Inhibitors of histone deacetylase |
| US7193105B2 (en) | 2002-05-22 | 2007-03-20 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors based on trihalomethylcarbonyl compounds |
| US8026280B2 (en) | 2001-03-27 | 2011-09-27 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors |
| CA2442366C (en) | 2001-03-27 | 2012-09-25 | Circagen Pharmaceutical, Llc | Histone deacetylase inhibitors |
| US6495719B2 (en) | 2001-03-27 | 2002-12-17 | Circagen Pharmaceutical | Histone deacetylase inhibitors |
| US7312247B2 (en) | 2001-03-27 | 2007-12-25 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors |
| DE60113645T2 (de) | 2001-04-10 | 2006-07-06 | Deutsches Krebsforschungszentrum Stiftung des öffentlichen Rechts | Verwendung von Histonedeacetylasehemmern zur Behandlung von Papillomaviren assoziierte Krankheiten |
| AR035455A1 (es) | 2001-04-23 | 2004-05-26 | Hoffmann La Roche | Derivados triciclicos de alquilhidroxamato , procesos para su elaboracion, composiciones farmaceuticas que los contienen, y el uso de dichos compuestos en la preparacion de medicamentos |
| 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 |
| WO2002090534A1 (en) | 2001-05-02 | 2002-11-14 | The Regents Of The University Of California | Method for treating neurodegenerative, psychiatric and other disorders with deacetylase inhibitors |
| US20030187027A1 (en) | 2001-05-09 | 2003-10-02 | Schreiber Stuart L. | Dioxanes and uses thereof |
| US7244853B2 (en) | 2001-05-09 | 2007-07-17 | President And Fellows Of Harvard College | Dioxanes and uses thereof |
| US7063973B2 (en) | 2001-06-14 | 2006-06-20 | Sloan-Kettering Institute For Cancer Research | HDAC9 polypeptides and polynucleotides and uses thereof |
| AU2002318364A1 (en) | 2001-06-14 | 2003-01-02 | Bristol-Myers Squibb Company | Novel human histone deacetylases |
| US7241743B2 (en) | 2001-06-15 | 2007-07-10 | The Trustees Of Columbia University In The City Of New York | Sir2α-based therapeutic and prophylactic methods |
| US6784173B2 (en) | 2001-06-15 | 2004-08-31 | Hoffmann-La Roche Inc. | Aromatic dicarboxylic acid derivatives |
| EP1407049A4 (en) | 2001-06-19 | 2005-03-23 | David Gladstone Inst | HISTON DEACETYLASE AND METHOD OF USE THEREOF |
| CA2451654A1 (en) | 2001-06-22 | 2003-01-03 | Ceres, Inc. | Chimeric histone acetyltransferase polypeptides |
| US20040186274A1 (en) | 2001-07-03 | 2004-09-23 | Allis C. David | Methylation of histone h4 at arginine 3 |
| WO2003014340A2 (en) | 2001-08-03 | 2003-02-20 | Novartis Ag | Human histone deacetylase-related gene and protein hdac10 |
| US20040266718A1 (en) | 2001-08-06 | 2004-12-30 | Zuomei Li | Inhibition of specific histone deacetylase isoforms |
| ITMI20011733A1 (it) | 2001-08-07 | 2003-02-07 | Italfarmaco Spa | Derivati dell'acido idrossamico inibitori degli enzimi istone deacetilasi, quali nuovi farmaci antiinfiammatori inibenti la sintesi di citoc |
| AR034897A1 (es) | 2001-08-07 | 2004-03-24 | Hoffmann La Roche | Derivados n-monoacilados de o-fenilendiaminas, sus analogos heterociclicos de seis miembros y su uso como agentes farmaceuticos |
| ATE526029T1 (de) | 2001-08-21 | 2011-10-15 | Astellas Pharma Inc | Medizinische verwendung eines histon-deacetylase- hemmers und verfahren zur beurteilung seiner antitumoralen wirkung |
| US20040259772A1 (en) | 2001-08-24 | 2004-12-23 | Antonio Fojo | Use of a histone deacetylase inhibitor to increase the entry of an adenoviral agent into a cell |
| EP1291015A1 (en) | 2001-09-10 | 2003-03-12 | Lunamed AG | Dosage forms having prolonged active ingredient release |
| US6897220B2 (en) | 2001-09-14 | 2005-05-24 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| US7868204B2 (en) | 2001-09-14 | 2011-01-11 | Methylgene Inc. | Inhibitors of histone deacetylase |
| EP1293205A1 (en) | 2001-09-18 | 2003-03-19 | G2M Cancer Drugs AG | Valproic acid and derivatives thereof for the combination therapy of human cancers, for the treatment of tumour metastasis and minimal residual disease |
| DE10148618B4 (de) | 2001-09-25 | 2007-05-03 | Schering Ag | Substituierte N-(1,4,5,6-Tetrahydro-cyclopentapyrazol-3-yl)-Derivate, deren Herstellung und Verwendung als Arzneimittel |
| 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 |
| GB0123664D0 (en) | 2001-10-02 | 2001-11-21 | Inst Of Cancer Res The | Histone deacetylase 9 |
| JP4638148B2 (ja) | 2001-10-16 | 2011-02-23 | スローン − ケタリング・インスティテュート・フォー・キャンサー・リサーチ | 神経変性疾患および脳の癌の処置 |
| WO2003033678A2 (en) | 2001-10-18 | 2003-04-24 | The Government Of The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Methods of using deacetylase inhibitors to promote cell differentiation and regeneration |
| RU2311200C2 (ru) | 2001-11-06 | 2007-11-27 | Новартис Аг | Комбинация ингибитора циклооксигеназы-2 и ингибитора гистондезацетилазы |
| CN1310937C (zh) | 2001-11-21 | 2007-04-18 | 犹太大学阿尔伯特爱因斯坦医学院 | Sir2产物及活性 |
| WO2003046207A2 (en) | 2001-11-27 | 2003-06-05 | Fred Hutchinson Cancer Research Center | Methods for inhibiting deacetylase activity |
| US20050227300A1 (en) | 2001-12-07 | 2005-10-13 | Atadja Peter W | Use of alpha-tubulin acetylation levels as a biomarker for protein deacetylase inhibitors |
| AU2002351898A1 (en) | 2001-12-21 | 2003-07-09 | Universite Libre De Bruxelles | Method for obtaining the elimination of integrated and functional viruses from infected mammal cells |
| US20060229236A1 (en) | 2001-12-28 | 2006-10-12 | Fujisawa Pharmaceutical Co. Ltd. | Cyclic tetrapeptide compound and use thereof |
| ITRM20020016A1 (it) | 2002-01-15 | 2003-07-15 | Sigma Tau Ind Farmaceuti | Derivati di acidi fenil(alchil)carbossilici e derivati fenilalchileterociclici dionici, loro uso come medicamenti ad attivita' ipoglicemizza |
| US20030165956A1 (en) | 2002-01-25 | 2003-09-04 | Board Of Regents, The University Of Texas System | Electrophoretic assay to predict risk of cancer and the efficacy and toxicity of cancer therapy |
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| CA2473505A1 (en) | 2002-02-07 | 2003-08-14 | Ellen M. Leahy | Novel bicyclic hydroxamates as inhibitors of histone deacetylase |
| WO2003066885A2 (en) | 2002-02-08 | 2003-08-14 | Novartis Ag | Method for screening for compounds having hdac inhibitory activity |
| EP1482962A4 (en) | 2002-02-15 | 2009-12-23 | Sloan Kettering Inst Cancer | METHOD OF TREATING THIOREDOXIN-MEDIATED DISEASES (TRX) |
| JP4274946B2 (ja) | 2002-02-20 | 2009-06-10 | 国立大学法人九州工業大学 | ヒストン脱アセチル化酵素阻害剤およびその製造方法 |
| WO2003070691A1 (en) | 2002-02-21 | 2003-08-28 | Osaka Industrial Promotion Organization | N-hydroxycarboxamide derivative |
| US7456219B2 (en) | 2002-03-04 | 2008-11-25 | Merck Hdac Research, Llc | Polymorphs of suberoylanilide hydroxamic acid |
| EP2322160A1 (en) | 2002-03-04 | 2011-05-18 | Merck HDAC Research, LLC | Methods of inducing terminal differentiation |
| US20040132825A1 (en) | 2002-03-04 | 2004-07-08 | Bacopoulos Nicholas G. | Methods of treating cancer with HDAC inhibitors |
| US7148257B2 (en) | 2002-03-04 | 2006-12-12 | Merck Hdac Research, Llc | Methods of treating mesothelioma with suberoylanilide hydroxamic acid |
| US7781161B2 (en) | 2002-03-07 | 2010-08-24 | The Johns Hopkins University School Of Medicine | Genomic screen for epigenetically silenced tumor suppressor genes |
| EP1497462A4 (en) | 2002-03-07 | 2007-11-07 | Univ Johns Hopkins Med | GENOMIC SCREEN ON EPIGENETIC MUTED CANCER ASSOCIATED GENES |
| AU2003218735B2 (en) | 2002-03-13 | 2009-03-12 | Janssen Pharmaceutica N.V. | Piperazinyl-, piperidinyl- and morpholinyl-derivatives as novel inhibitors of histone deacetylase |
| CN1305850C (zh) | 2002-03-13 | 2007-03-21 | 詹森药业有限公司 | 作为组蛋白脱乙酰酶新颖抑制剂的磺酰基氨基衍生物 |
| EA006707B1 (ru) | 2002-03-13 | 2006-02-24 | Янссен Фармацевтика Н. В. | Сульфонилпроизводные в качестве новых ингибиторов гистон-деацетилазы |
| OA12790A (en) | 2002-03-13 | 2006-07-10 | Janssen Pharmaceutica Nv | New inhibitors of histone deacetylase. |
| PL205531B1 (pl) | 2002-03-13 | 2010-04-30 | Janssen Pharmaceutica Nv | Pochodna karbonyloaminowa, jej zastosowanie i sposób wytwarzania oraz kompozycja farmaceutyczna |
| EP1488005A1 (fr) | 2002-03-26 | 2004-12-22 | Exhonit Therapeutics SA | Histone deacetylase : nouvelle cible moleculaire de la neurotoxicite |
| US20040077591A1 (en) | 2002-03-28 | 2004-04-22 | The Brigham And Women's Hospital, Inc. | Histone deacetylase inhibitors for the treatment of multiple sclerosis, amyotrophic lateral sclerosis and Alzheimer's Disease |
| US6841565B1 (en) | 2002-03-29 | 2005-01-11 | The Ohio State University | Treatment of patients with chronic lymphocytic leukemia |
| NZ536116A (en) | 2002-04-03 | 2007-01-26 | Topotarget Uk Ltd | Carbamic acid compounds comprising a piperazine linkage as HDAC inhibitors |
| WO2003084611A1 (en) | 2002-04-05 | 2003-10-16 | Fujisawa Pharmaceutical Co., Ltd. | Depsipeptide for therapy of kidney cancer |
| TWI319387B (en) | 2002-04-05 | 2010-01-11 | Astrazeneca Ab | Benzamide derivatives |
| WO2003087066A1 (en) | 2002-04-11 | 2003-10-23 | Sk Chemicals, Co., Ltd. | α,β-UNSATURATED HYDROXAMIC ACID DERIVATIVES AND THEIR USE AS HISTONE DEACETYLASE INHIBITORS |
| MY134200A (en) | 2002-04-12 | 2007-11-30 | Kowa Co | Method for treating cancer |
| MXPA04010199A (es) | 2002-04-15 | 2005-07-05 | Sloan Kettering Inst Cancer | Terapia en combinacion para el tratamiento de cancer. |
| US6620838B1 (en) | 2002-04-19 | 2003-09-16 | Signal Pharmaceuticals, Inc. | Benzopyrazone compounds, compositions thereof, and methods of treatment therewith |
| US20030206946A1 (en) | 2002-04-26 | 2003-11-06 | Yih-Lin Chung | Methods for therapy of connective tissue disease |
| US6809118B2 (en) | 2002-07-25 | 2004-10-26 | Yih-Lin Chung | Methods for therapy of radiation cutaneous syndrome |
| GB0209715D0 (en) | 2002-04-27 | 2002-06-05 | Astrazeneca Ab | Chemical compounds |
| US20040018522A1 (en) | 2002-05-09 | 2004-01-29 | Brigham And Women's Hospital, Inc. | Identification of dysregulated genes in patients with multiple sclerosis |
| EP1362914A3 (en) | 2002-05-15 | 2004-05-06 | Schering AG | Histone deacetylase inhibitor and use thereof |
| US7351542B2 (en) | 2002-05-20 | 2008-04-01 | The Regents Of The University Of California | Methods of modulating tubulin deacetylase activity |
| EP1511729A4 (en) | 2002-05-22 | 2006-09-06 | Errant Gene Therapeutics Llc | HISTONDEACETYLASEINHIBITORS BASED ON ALPHACHALCOGEN METHYL CARBONYL COMPOUNDS |
| EP1511477A4 (en) | 2002-05-22 | 2008-04-09 | Errant Gene Therapeutics Llc | HISTONE DEACETYLASE INHIBITORS BASED ON ALPHA-KETO-EPOXYDE COMPOUNDS |
| ATE497015T1 (de) | 2002-05-23 | 2011-02-15 | Univ California | Verfahren zum auswählen von modulatoren der mitochondrialen nad-abhängigen deacetylase, sirt3 |
| US20030224473A1 (en) | 2002-05-23 | 2003-12-04 | Mccafferty Dewey G. | Methods for screening for histone deacetylase activity and for identifying histone deacetylase inhibitors |
| US20040002447A1 (en) | 2002-06-04 | 2004-01-01 | Regents Of The University Of California | Induction of insulin expression |
| AU2003242646A1 (en) | 2002-06-10 | 2003-12-22 | Novartis Ag | Combinations comprising epothilones and pharmaceutical uses thereof |
| WO2004001072A2 (en) | 2002-06-19 | 2003-12-31 | Oncotherapy Science, Inc. | Method for diagnosis of colorectal tumors |
| US20050084967A1 (en) | 2002-06-28 | 2005-04-21 | Xcyte Therapies, Inc. | Compositions and methods for eliminating undesired subpopulations of T cells in patients with immunological defects related to autoimmunity and organ or hematopoietic stem cell transplantation |
| MXPA05000255A (es) | 2002-07-01 | 2005-07-15 | Pharmacia & Upjohn Co Llc | Inhibidores de polimerasa de ns5b de hcv. |
| US20040072770A1 (en) | 2002-07-03 | 2004-04-15 | Besterman Jeffrey M. | Methods for specifically inhibiting histone deacetylase-7 and 8 |
| SE0202157D0 (sv) | 2002-07-09 | 2002-07-09 | Biovitrum Ab | Methods for identification of compounds modulating insulin resistance |
| GB0215844D0 (en) | 2002-07-09 | 2002-08-14 | Novartis Ag | Organic compounds |
| WO2004009092A1 (en) | 2002-07-17 | 2004-01-29 | Chemgenex Pharmaceuticals Limited | Formulations and methods of administration of cephalotaxines, including homoharringtonine |
| NZ537759A (en) | 2002-07-17 | 2006-10-27 | Titan Pharmaceuticals Inc | Combination of chemotherapeutic drugs for increasing antitumor activity |
| US20050176686A1 (en) | 2002-07-23 | 2005-08-11 | 4Sc Ag | Novel compounds as histone deacetylase inhibitors |
| DE10233412A1 (de) | 2002-07-23 | 2004-02-12 | 4Sc Ag | Neue Verbindungen als Histondeacetylase-Inhibitoren |
| US20050065596A1 (en) | 2002-07-24 | 2005-03-24 | Xufan Tseng | Stents capable of controllably releasing histone deacetylase inhibitors |
| US20080145928A1 (en) | 2002-07-25 | 2008-06-19 | Shuki Mizutani | Factor Taking Part in Transcription Control |
| RU2005105696A (ru) | 2002-08-02 | 2005-11-10 | Арджента Дискавери Лимитед (Gb) | Замещенные тиенилгидроксамовые кислоты в качестве ингибиторов гистондеацетилазы |
| WO2004017996A1 (ja) | 2002-08-20 | 2004-03-04 | Yamanouchi Pharmaceutical Co., Ltd. | 関節軟骨細胞外マトリクス分解阻害剤 |
| EP1548026A4 (en) | 2002-08-30 | 2006-03-22 | Yamanouchi Pharma Co Ltd | NEW DEPSIPEPTID CONNECTION |
| AU2003259521A1 (en) | 2002-09-13 | 2004-04-30 | Mcguire Va Medical Center 111K | 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 |
| EP1400806A1 (en) | 2002-09-18 | 2004-03-24 | G2M Cancer Drugs AG | The use of molecular markers for the preclinical and clinical profiling of inhibitors of enzymes having histone deacetylase activity |
| US20040127571A1 (en) | 2002-09-19 | 2004-07-01 | University Of South Florida | Method of Treating Leukemia with a Combination of Suberoylanilide Hydromaxic Acid and Imatinib Mesylate |
| EP1403639A1 (en) | 2002-09-30 | 2004-03-31 | G2M Cancer Drugs AG | Antibody tools for the diagnostic use in the medical therapy with inhibitors of histone deacetylases |
| US20040077083A1 (en) | 2002-10-17 | 2004-04-22 | Isis Pharmaceuticals Inc. | Antisense modulation of histone deacetylase 4 expression |
| KR20050074487A (ko) | 2002-10-17 | 2005-07-18 | 메틸진, 인크. | 히스톤 데아세틸라아제의 억제제 |
| US20040077084A1 (en) | 2002-10-17 | 2004-04-22 | Isis Pharmaceuticals Inc. | Antisense modulation of histone deacetylase 4 expression |
| JP2006512318A (ja) | 2002-11-12 | 2006-04-13 | アルコン，インコーポレイテッド | 眼の血管新生もしくは水腫状の疾患および障害を処置するためのヒストンデアセチラーゼインヒビター |
| KR20050074547A (ko) | 2002-11-12 | 2005-07-18 | 알콘, 인코퍼레이티드 | 눈의 퇴행성 질환을 치료하기 위한 히스톤 디아세틸라제저해제 |
| AU2003295444A1 (en) | 2002-11-15 | 2004-06-15 | The Board Of Trustees Of The University Of Illinois | Methods for in vitro expansion of hematopoietic stem cells |
| GB0226855D0 (en) | 2002-11-18 | 2002-12-24 | Queen Mary & Westfield College | Histone deacetylase inhibitors |
| JP2006508986A (ja) | 2002-11-20 | 2006-03-16 | エルラント ゲネ セラペウチクス エルエルシー | ヒストンデアセチラーゼ阻害剤による肺細胞の治療方法 |
| WO2004052292A2 (en) | 2002-12-06 | 2004-06-24 | University Of South Florida | Histone deacetylase inhibitor enhancement of trail-induced apoptosis |
| TW200426138A (en) | 2002-12-10 | 2004-12-01 | Hoffmann La Roche | Novel arylene-carboxylic acid (2-amino-phenyl)-amide derivatives, their manufacture and use as pharmaceutical agents |
| EP1590318A2 (en) | 2002-12-12 | 2005-11-02 | Jawaharlal Nehru Centre For Advanced Scientific Research | Modulators (inhibitors/activators) of histone acetyltransferases |
| US7098241B2 (en) | 2002-12-16 | 2006-08-29 | Hoffmann-La Roche Inc. | Thiophene hydroxamic acid derivatives |
| ITMI20022745A1 (it) | 2002-12-23 | 2004-06-24 | Coimex Scrl United Companies | Esteri misti dell'acido ialuronico ad attivita' citostatica e prodifferenziante e procedimento per la loro produzione. |
| WO2004058234A2 (en) | 2002-12-27 | 2004-07-15 | Schering Aktiengesellschaft | Pharmaceutical combinations of phthalazine vegf inhibitors and benzamide hdac inhibitors |
| US20040197888A1 (en) | 2002-12-31 | 2004-10-07 | Armour Christopher D. | Alternatively spliced isoforms of histone deacetylase 3 (HDAC3) |
| ITMI20030025A1 (it) | 2003-01-10 | 2004-07-11 | Italfarmaco Spa | Derivati dell'acido idrossammico ad attivita' antinfiammatoria. |
| US7135493B2 (en) | 2003-01-13 | 2006-11-14 | Astellas Pharma Inc. | HDAC inhibitor |
| WO2004064727A2 (en) | 2003-01-16 | 2004-08-05 | Georgetown University | Method of cancer treatment using hdac inhibitors |
| US7465719B2 (en) | 2003-01-17 | 2008-12-16 | Topotarget Uk Limited | Carbamic acid compounds comprising an ester or ketone linkage as HDAC inhibitors |
| WO2004067480A2 (en) | 2003-01-25 | 2004-08-12 | Oxford Glycosciences (Uk) Ltd | Substituted phenylurea derivatives as hdac inhibitors |
| WO2004069158A2 (en) | 2003-01-27 | 2004-08-19 | Merck & Co., Inc. | Substituted pyrazoles, compositions containing such compounds and methods of use |
| TW200424174A (en) | 2003-02-06 | 2004-11-16 | Hoffmann La Roche | New TP diamide |
| US7208491B2 (en) | 2003-02-07 | 2007-04-24 | Hoffmann-La Roche Inc. | N-monoacylated o-phenylenediamines |
| WO2004072265A2 (en) | 2003-02-11 | 2004-08-26 | Wyeth | Methods for monitoring drug activities in vivo |
| AU2003900608A0 (en) | 2003-02-11 | 2003-02-27 | Fujisawa Pharmaceutical Co., Ltd. | Hdac inhibitor |
| AU2003900587A0 (en) | 2003-02-11 | 2003-02-27 | Fujisawa Pharmaceutical Co., Ltd. | Hdac inhibitor |
| WO2004071464A2 (en) | 2003-02-12 | 2004-08-26 | Johns Hopkins University School Of Medicine | Diagnostic application of differentially-expressed genes in lympho-hematopoietic stem cells |
| WO2004071443A2 (en) | 2003-02-12 | 2004-08-26 | Irm Llc | Methods and compositions for modulating stem cells |
| US7244751B2 (en) | 2003-02-14 | 2007-07-17 | Shenzhen Chipscreen Biosciences Ltd. | Histone deacetylase inhibitors of novel benzamide derivatives with potent differentiation and anti-proliferation activity |
| WO2004074478A1 (ja) | 2003-02-19 | 2004-09-02 | Astellas Pharma Inc. | ヒストンデアセチラーゼ阻害剤の抗腫瘍効果の予測方法 |
| US7652036B2 (en) | 2003-02-25 | 2010-01-26 | Topotarget Uk Limited | Carbamic acid compounds comprising a bicyclic heteroaryl group as HDAC inhibitors |
| CA2518318A1 (en) | 2003-03-17 | 2004-09-30 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| WO2004089293A2 (en) | 2003-04-01 | 2004-10-21 | Memorial Sloan-Kettering Cancer Center | Hydroxamic acid compounds and methods of use thereof |
| TW200424187A (en) | 2003-04-04 | 2004-11-16 | Hoffmann La Roche | New oxime derivatives and their use as pharmaceutically active agents |
| PT1611088E (pt) | 2003-04-07 | 2009-09-24 | Pharmacyclics Inc | Hidroxamatos como agentes terapêuticos |
| CN1809559B (zh) | 2003-04-18 | 2010-06-02 | 记忆药物公司 | 作为磷酸二酯酶4抑制剂的吡唑衍生物 |
| US20040213826A1 (en) | 2003-04-28 | 2004-10-28 | Marx Steven O. | Medical devices and methods for inhibiting proliferation of smooth muscle cells |
| CN1791396A (zh) | 2003-05-21 | 2006-06-21 | 诺瓦提斯公司 | 组蛋白脱乙酰基酶抑制剂与化疗剂的组合 |
| MXPA05012619A (es) | 2003-05-21 | 2006-02-08 | Univ Texas | Inhibicion de la proteina cinasa c-mu como un tratamiento para la hipertrofia cardiaca y la falla cardiaca. |
| PE20050206A1 (es) | 2003-05-26 | 2005-03-26 | Schering Ag | Composicion farmaceutica que contiene un inhibidor de histona deacetilasa |
| US20050020557A1 (en) | 2003-05-30 | 2005-01-27 | Kosan Biosciences, Inc. | Method for treating diseases using HSP90-inhibiting agents in combination with enzyme inhibitors |
| BRPI0411275A (pt) | 2003-06-10 | 2006-08-01 | Kalypsys Inc | compostos de carbonila como inibidores de histona deacetilase para tratamento de doenças; composição farmacêutica; método de modular a atividade catalìtica de hdac; método de tratar doença em um indivìduo; utilização de um composto ou composição; método de inibir hdac |
| US7271195B2 (en) | 2003-06-10 | 2007-09-18 | Kalypsys, Inc. | Carbonyl compounds as inhibitors of histone deacetylase for the treatment of disease |
| US20060235012A1 (en) | 2003-06-16 | 2006-10-19 | Chroma Therapeutics Limited | Carboline and betacarboline derivatives for use as hdac enzyme inhibitors |
| EP1491188A1 (en) | 2003-06-25 | 2004-12-29 | G2M Cancer Drugs AG | Topical use of valproic acid for the prevention or treatment of skin disorders |
| EP1638541B1 (en) | 2003-06-27 | 2010-05-19 | Astellas Pharma Inc. | Therapeutic agent for soft tissue sarcoma |
| AU2004253579B2 (en) | 2003-07-01 | 2010-12-23 | Biomol International L.P. | Sirt1 modulators for manipulating cells/organism lifespan/stress response |
| CA2531253A1 (en) | 2003-07-02 | 2005-02-24 | Vern L. Schramm | Sir2 regulation |
| CA2531661C (en) | 2003-07-07 | 2013-03-12 | Georgetown University | Histone deacetylase inhibitors and methods of use thereof |
| US7842835B2 (en) | 2003-07-07 | 2010-11-30 | Georgetown University | Histone deacetylase inhibitors and methods of use thereof |
| US7723376B2 (en) | 2003-07-15 | 2010-05-25 | Korea Research Institute Of Bioscience And Biotechnology | 2-oxo-heterocyclic compounds and pharmaceutical compositions |
| GB0316889D0 (en) | 2003-07-18 | 2003-08-20 | Univ London | Pharmaceutical agents |
| US20050037992A1 (en) | 2003-07-22 | 2005-02-17 | John Lyons | Composition and method for treating neurological disorders |
| WO2005011598A2 (en) | 2003-07-31 | 2005-02-10 | University Of South Florida | Leukemia treatment method and composition |
| WO2005014588A1 (en) | 2003-08-01 | 2005-02-17 | Argenta Discovery Limited | Substituted thienyl-hydroxamic acids having histone deacetylase activity |
| US20050032794A1 (en) | 2003-08-05 | 2005-02-10 | Padia Janak K. | Diamine derivatives of quinone and uses thereof |
| 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 |
| BRPI0413439A (pt) | 2003-08-08 | 2006-10-17 | Novartis Ag | combinações compreendendo estaurosporinas |
| NZ542711A (en) | 2003-08-20 | 2008-03-28 | Pharmacyclics Inc | Acetylene derivatives as inhibitors of histone deacetylase |
| PT1663194E (pt) | 2003-08-26 | 2010-07-06 | Merck Hdac Res Llc | Utilizaão de saha para o tratamento de mesotelioma |
| CN1964714B (zh) | 2003-08-29 | 2011-09-28 | Hdac默克研究有限责任公司 | 辛二酰苯胺异羟肟酸和吉西他滨在制备用于治疗癌症的药物中的用途 |
| US20050059682A1 (en) | 2003-09-12 | 2005-03-17 | Supergen, Inc., A Delaware Corporation | Compositions and methods for treatment of cancer |
| US8404458B2 (en) | 2003-09-16 | 2013-03-26 | The Rockefeller University | Histone modifications as binary switches controlling gene expression |
| AU2004283196B2 (en) | 2003-09-17 | 2011-08-25 | Janssen Pharmaceutica, N.V. | Fused heterocyclic compounds |
| EP1667720A1 (en) | 2003-09-18 | 2006-06-14 | Novartis AG | Combination of a histone deacetylase inhibitor with a death receptor ligand |
| MY142589A (en) | 2003-09-22 | 2010-12-15 | S Bio Pte Ltd | Benzimidazole derivatives : preparation and pharmaceutical applications |
| WO2005030705A1 (en) | 2003-09-24 | 2005-04-07 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| MXPA06003222A (es) | 2003-09-25 | 2006-05-22 | Astellas Pharma Inc | Agente antitumoral que comprende un inhibidor de histona desacetilasa y un inhibidor de topoisomerasa ii. |
| WO2005034880A2 (en) | 2003-10-09 | 2005-04-21 | Aton Pharma, Inc. | Thiophene and benzothiophene hydroxamic acid derivatives |
| US20050124625A1 (en) | 2003-10-21 | 2005-06-09 | Salvati Mark E. | Piperazine derivatives and their use as modulators of nuclear hormone receptor function |
| JP2007509930A (ja) | 2003-10-27 | 2007-04-19 | エス＊バイオ プライベート リミティッド | アシル尿素およびスルホニル尿素が結合したヒドロキサマート |
| TW200524575A (en) | 2003-10-27 | 2005-08-01 | S Bio Pte Ltd | Biaryl linked hydroxamates: preparation and pharmaceutical applications |
| IN2003CH00929A (enExample) | 2003-11-13 | 2008-10-06 | ||
| WO2005053609A2 (en) | 2003-11-26 | 2005-06-16 | Guilford Pharmaceuticals Inc. | Methods of nad+-dependent deacetylase inhibitors |
| US20090023718A1 (en) | 2003-11-26 | 2009-01-22 | Aton Pharma, Inc. | Diamine and Iminodiacetic Acid Hydroxamic Acid Derivatives |
| US20080004290A1 (en) | 2003-11-28 | 2008-01-03 | The University Of Queensland | Anti-Cancer Agents |
| EP1696898B1 (en) | 2003-12-02 | 2015-11-18 | The Ohio State University Research Foundation | Zn 2+ -chelating motif-tethered short-chain fatty acids as a novel class of histone deacetylase inhibitors |
| EP1713460A2 (en) | 2003-12-10 | 2006-10-25 | Wisconsin Alumni Research Foundation | Fk228 analogs and their use as hdac-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 |
| US20050159470A1 (en) | 2003-12-19 | 2005-07-21 | Syrrx, Inc. | Histone deacetylase inhibitors |
| US8652502B2 (en) | 2003-12-19 | 2014-02-18 | Cordis Corporation | Local vascular delivery of trichostatin A alone or in combination with sirolimus to prevent restenosis following vascular injury |
| US20050171027A1 (en) | 2003-12-29 | 2005-08-04 | President And Fellows Of Harvard College | Compositions for treating or preventing obesity and insulin resistance disorders |
| EP1709176A1 (en) | 2004-01-21 | 2006-10-11 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. | Inhibitors of mammalian hdac 11 useful for treating hdac 11 mediated disorders |
| WO2005092899A1 (en) | 2004-03-26 | 2005-10-06 | Methylgene Inc. | Inhibitors of histone deacetylase |
| US7253204B2 (en) | 2004-03-26 | 2007-08-07 | Methylgene Inc. | Inhibitors of histone deacetylase |
| EP1824831A2 (en) | 2004-12-16 | 2007-08-29 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| JP2008540574A (ja) | 2005-05-11 | 2008-11-20 | タケダ サン ディエゴ インコーポレイテッド | ヒストンデアセチラーゼ阻害剤 |
| CN101263121A (zh) | 2005-07-14 | 2008-09-10 | 塔克达圣地亚哥公司 | 组蛋白脱乙酰基酶抑制剂 |
-
2006
- 2006-05-10 JP JP2008511453A patent/JP2008540574A/ja active Pending
- 2006-05-10 WO PCT/US2006/018645 patent/WO2006122319A2/en not_active Ceased
- 2006-05-10 US US11/382,659 patent/US7642253B2/en not_active Expired - Fee Related
- 2006-05-10 EP EP06759801A patent/EP1896436A2/en not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003024448A2 (en) * | 2001-09-14 | 2003-03-27 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| JP2003137866A (ja) * | 2001-11-01 | 2003-05-14 | Sankyo Co Ltd | フェニレンジアミン誘導体 |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009536615A (ja) * | 2006-04-07 | 2009-10-15 | メシルジーン インコーポレイテッド | ヒストンデアセチラーゼの阻害剤 |
| JP2012510512A (ja) * | 2008-12-03 | 2012-05-10 | マサチューセッツ インスティテュート オブ テクノロジー | 記憶を推進するためのｈｄａｃ２の阻害 |
| US8841346B2 (en) | 2009-10-30 | 2014-09-23 | Massachusetts Institute Of Technology | Use of CI-994 and dinaline for the treatment of memory/cognition and anxiety disorders |
| JP2015521999A (ja) * | 2012-07-03 | 2015-08-03 | ヘプタレス セラピューティクス リミテッドＨｅｐｔａｒｅｓ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｌｉｍｉｔｅｄ | オレキシン受容体アンタゴニスト |
| JP2018135349A (ja) * | 2012-07-03 | 2018-08-30 | ヘプタレス セラピューティクス リミテッドＨｅｐｔａｒｅｓ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｌｉｍｉｔｅｄ | オレキシン受容体アンタゴニスト |
| JP2020503268A (ja) * | 2016-11-23 | 2020-01-30 | リージェナシー・ファーマシューティカルズ・エルエルシー | 選択的ｈｄａｃ１、２阻害剤としてのピペラジン誘導体 |
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Also Published As
| Publication number | Publication date |
|---|---|
| WO2006122319A2 (en) | 2006-11-16 |
| EP1896436A2 (en) | 2008-03-12 |
| US20060258694A1 (en) | 2006-11-16 |
| WO2006122319A3 (en) | 2007-11-15 |
| US7642253B2 (en) | 2010-01-05 |
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