ZA200507933B - Acetylene derivatives as inhibitors of histone deacetylase - Google Patents
Acetylene derivatives as inhibitors of histone deacetylase Download PDFInfo
- Publication number
- ZA200507933B ZA200507933B ZA200507933A ZA200507933A ZA200507933B ZA 200507933 B ZA200507933 B ZA 200507933B ZA 200507933 A ZA200507933 A ZA 200507933A ZA 200507933 A ZA200507933 A ZA 200507933A ZA 200507933 B ZA200507933 B ZA 200507933B
- Authority
- ZA
- South Africa
- Prior art keywords
- hydroxy
- benzamide
- ynyl
- prop
- optionally substituted
- Prior art date
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- 102000003964 Histone deacetylase Human genes 0.000 title claims abstract description 16
- 108090000353 Histone deacetylase Proteins 0.000 title claims abstract description 16
- 239000003112 inhibitor Substances 0.000 title abstract description 4
- 150000000475 acetylene derivatives Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 48
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 12
- 201000010099 disease Diseases 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- -1 aralkenyl Chemical group 0.000 claims description 115
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 125000001072 heteroaryl group Chemical group 0.000 claims description 41
- 125000001188 haloalkyl group Chemical group 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 16
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000003282 alkyl amino group Chemical group 0.000 claims description 14
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 14
- 206010028980 Neoplasm Diseases 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 11
- 150000002431 hydrogen Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 201000011510 cancer Diseases 0.000 claims description 10
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 9
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims description 8
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 8
- 125000002431 aminoalkoxy group Chemical group 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 229940075993 receptor modulator Drugs 0.000 claims description 4
- 102000027483 retinoid hormone receptors Human genes 0.000 claims description 4
- 108091008679 retinoid hormone receptors Proteins 0.000 claims description 4
- VEEGZPWAAPPXRB-BJMVGYQFSA-N (3e)-3-(1h-imidazol-5-ylmethylidene)-1h-indol-2-one Chemical compound O=C1NC2=CC=CC=C2\C1=C/C1=CN=CN1 VEEGZPWAAPPXRB-BJMVGYQFSA-N 0.000 claims description 3
- 229940122440 HIV protease inhibitor Drugs 0.000 claims description 3
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 3
- 229940123468 Transferase inhibitor Drugs 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000004037 angiogenesis inhibitor Substances 0.000 claims description 3
- 229940121369 angiogenesis inhibitor Drugs 0.000 claims description 3
- 230000001028 anti-proliverative effect Effects 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- 239000002254 cytotoxic agent Substances 0.000 claims description 3
- 229940127089 cytotoxic agent Drugs 0.000 claims description 3
- 231100000599 cytotoxic agent Toxicity 0.000 claims description 3
- 239000002834 estrogen receptor modulator Substances 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 239000004030 hiv protease inhibitor Substances 0.000 claims description 3
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 3
- 230000001404 mediated effect Effects 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims description 3
- 239000000849 selective androgen receptor modulator Substances 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 239000003558 transferase inhibitor Substances 0.000 claims 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 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000001959 radiotherapy Methods 0.000 claims description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 12
- 125000001475 halogen functional group Chemical group 0.000 claims 7
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 4
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 claims 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 3
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 2
- JCESBYWAUYAJFN-UHFFFAOYSA-N n-[1-[2-[4-(hydroxycarbamoyl)phenyl]ethynyl]cycloheptyl]-1-benzofuran-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1C#CC1(NC(=O)C=2OC3=CC=CC=C3C=2)CCCCCC1 JCESBYWAUYAJFN-UHFFFAOYSA-N 0.000 claims 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 2
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 1
- BDNKPCHNEHWOQN-UHFFFAOYSA-N 4-[2-(dimethylamino)ethoxy]-n-[3-[4-(hydroxycarbamoyl)phenyl]prop-2-ynyl]quinoline-2-carboxamide;hydrochloride Chemical compound Cl.N=1C2=CC=CC=C2C(OCCN(C)C)=CC=1C(=O)NCC#CC1=CC=C(C(=O)NO)C=C1 BDNKPCHNEHWOQN-UHFFFAOYSA-N 0.000 claims 1
- MQUHMHQDGXTVPF-UHFFFAOYSA-N 4-[3-(benzenesulfonamido)prop-1-ynyl]-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C#CCNS(=O)(=O)C1=CC=CC=C1 MQUHMHQDGXTVPF-UHFFFAOYSA-N 0.000 claims 1
- NBDCYIDNRORIMI-UHFFFAOYSA-N 5-chloro-n-[3-[4-(hydroxycarbamoyl)phenyl]prop-2-ynyl]-1-benzofuran-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1C#CCNC(=O)C1=CC2=CC(Cl)=CC=C2O1 NBDCYIDNRORIMI-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 1
- WRFKUXMGEDUMNV-UHFFFAOYSA-N n-[1-[2-[4-(hydroxycarbamoyl)phenyl]ethynyl]cyclobutyl]-1-benzofuran-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1C#CC1(NC(=O)C=2OC3=CC=CC=C3C=2)CCC1 WRFKUXMGEDUMNV-UHFFFAOYSA-N 0.000 claims 1
- IZIWRYGEWPYYDQ-UHFFFAOYSA-N n-[1-[2-[4-(hydroxycarbamoyl)phenyl]ethynyl]cycloheptyl]-1h-indole-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1C#CC1(NC(=O)C=2NC3=CC=CC=C3C=2)CCCCCC1 IZIWRYGEWPYYDQ-UHFFFAOYSA-N 0.000 claims 1
- ASVMYAVFNXMWRR-UHFFFAOYSA-N n-[1-[2-[4-(hydroxycarbamoyl)phenyl]ethynyl]cyclohexyl]-1h-indole-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1C#CC1(NC(=O)C=2NC3=CC=CC=C3C=2)CCCCC1 ASVMYAVFNXMWRR-UHFFFAOYSA-N 0.000 claims 1
- OXSHUUVHAAXLSN-UHFFFAOYSA-N n-[1-[2-[4-(hydroxycarbamoyl)phenyl]ethynyl]cyclopentyl]-1h-indole-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1C#CC1(NC(=O)C=2NC3=CC=CC=C3C=2)CCCC1 OXSHUUVHAAXLSN-UHFFFAOYSA-N 0.000 claims 1
- FOZGVQCLTLQFKD-UHFFFAOYSA-N n-[1-[2-[4-(hydroxycarbamoyl)phenyl]ethynyl]cyclopropyl]-1-benzofuran-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1C#CC1(NC(=O)C=2OC3=CC=CC=C3C=2)CC1 FOZGVQCLTLQFKD-UHFFFAOYSA-N 0.000 claims 1
- SJWKTENSWNKKBJ-UHFFFAOYSA-N n-[1-[2-[4-(hydroxycarbamoyl)phenyl]ethynyl]cyclopropyl]-1h-indole-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1C#CC1(NC(=O)C=2NC3=CC=CC=C3C=2)CC1 SJWKTENSWNKKBJ-UHFFFAOYSA-N 0.000 claims 1
- UOAFFSVBNHTIRW-UHFFFAOYSA-N n-[1-[2-[4-(hydroxycarbamoyl)phenyl]ethynyl]cyclopropyl]-4-methoxy-1h-indole-2-carboxamide Chemical compound C=1C=2C(OC)=CC=CC=2NC=1C(=O)NC1(C#CC=2C=CC(=CC=2)C(=O)NO)CC1 UOAFFSVBNHTIRW-UHFFFAOYSA-N 0.000 claims 1
- SVVURDUJLZFOKI-UHFFFAOYSA-N n-[3-[2-[4-(hydroxycarbamoyl)phenyl]ethynyl]oxolan-3-yl]-1h-indole-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1C#CC1(NC(=O)C=2NC3=CC=CC=C3C=2)COCC1 SVVURDUJLZFOKI-UHFFFAOYSA-N 0.000 claims 1
- AHVPJXXZRUQZPC-UHFFFAOYSA-N n-[3-[4-(hydroxycarbamoyl)phenyl]prop-2-ynyl]-1,3-benzothiazole-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1C#CCNC(=O)C1=NC2=CC=CC=C2S1 AHVPJXXZRUQZPC-UHFFFAOYSA-N 0.000 claims 1
- TVKACPYDSHRTLF-UHFFFAOYSA-N n-[3-[4-(hydroxycarbamoyl)phenyl]prop-2-ynyl]-1-benzofuran-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1C#CCNC(=O)C1=CC2=CC=CC=C2O1 TVKACPYDSHRTLF-UHFFFAOYSA-N 0.000 claims 1
- IWNDFCVDKUSWCA-UHFFFAOYSA-N n-[3-[4-(hydroxycarbamoyl)phenyl]prop-2-ynyl]-1-benzothiophene-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1C#CCNC(=O)C1=CC2=CC=CC=C2S1 IWNDFCVDKUSWCA-UHFFFAOYSA-N 0.000 claims 1
- PBKOVUVEZBDOFT-UHFFFAOYSA-N n-[3-[4-(hydroxycarbamoyl)phenyl]prop-2-ynyl]-1h-benzimidazole-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1C#CCNC(=O)C1=NC2=CC=CC=C2N1 PBKOVUVEZBDOFT-UHFFFAOYSA-N 0.000 claims 1
- LDUKXIDHSRRXAJ-UHFFFAOYSA-N n-[3-[4-(hydroxycarbamoyl)phenyl]prop-2-ynyl]-3-(2,2,2-trifluoroethoxymethyl)-1-benzofuran-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1C#CCNC(=O)C1=C(COCC(F)(F)F)C2=CC=CC=C2O1 LDUKXIDHSRRXAJ-UHFFFAOYSA-N 0.000 claims 1
- KLYRCBUCYKBZAG-UHFFFAOYSA-N n-[3-[4-(hydroxycarbamoyl)phenyl]prop-2-ynyl]-3-(2-methoxyethoxymethyl)-1-benzofuran-2-carboxamide Chemical compound O1C2=CC=CC=C2C(COCCOC)=C1C(=O)NCC#CC1=CC=C(C(=O)NO)C=C1 KLYRCBUCYKBZAG-UHFFFAOYSA-N 0.000 claims 1
- HNTXDHRBLHIHFT-UHFFFAOYSA-N n-[3-[4-(hydroxycarbamoyl)phenyl]prop-2-ynyl]-4-(trifluoromethyl)-1-benzothiophene-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1C#CCNC(=O)C1=CC2=C(C(F)(F)F)C=CC=C2S1 HNTXDHRBLHIHFT-UHFFFAOYSA-N 0.000 claims 1
- SBLLSHQKVOTPIY-UHFFFAOYSA-N n-[3-[4-(hydroxycarbamoyl)phenyl]prop-2-ynyl]-4-methoxy-1h-indole-2-carboxamide Chemical compound C=1C=2C(OC)=CC=CC=2NC=1C(=O)NCC#CC1=CC=C(C(=O)NO)C=C1 SBLLSHQKVOTPIY-UHFFFAOYSA-N 0.000 claims 1
- OSYZISMRFVYSRT-UHFFFAOYSA-N n-[3-[4-(hydroxycarbamoyl)phenyl]prop-2-ynyl]-5-(2-methoxyethoxy)-1-benzofuran-2-carboxamide Chemical compound C=1C2=CC(OCCOC)=CC=C2OC=1C(=O)NCC#CC1=CC=C(C(=O)NO)C=C1 OSYZISMRFVYSRT-UHFFFAOYSA-N 0.000 claims 1
- DQVXBMDRIMJEEJ-UHFFFAOYSA-N n-[3-[4-(hydroxycarbamoyl)phenyl]prop-2-ynyl]-5-(2-methoxyethoxymethyl)-1h-indole-2-carboxamide Chemical compound C=1C2=CC(COCCOC)=CC=C2NC=1C(=O)NCC#CC1=CC=C(C(=O)NO)C=C1 DQVXBMDRIMJEEJ-UHFFFAOYSA-N 0.000 claims 1
- JZLYZFOVWHHWLB-UHFFFAOYSA-N n-[3-[4-(hydroxycarbamoyl)phenyl]prop-2-ynyl]-5-(2-morpholin-4-ylethoxy)-1-benzofuran-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(C(=O)NO)=CC=C1C#CCNC(=O)C1=CC2=CC(OCCN3CCOCC3)=CC=C2O1 JZLYZFOVWHHWLB-UHFFFAOYSA-N 0.000 claims 1
- HATAILRFKNVFOS-UHFFFAOYSA-N n-[3-[4-(hydroxycarbamoyl)phenyl]prop-2-ynyl]-5-(2-pyrrolidin-1-ylethoxy)-1-benzofuran-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(C(=O)NO)=CC=C1C#CCNC(=O)C1=CC2=CC(OCCN3CCCC3)=CC=C2O1 HATAILRFKNVFOS-UHFFFAOYSA-N 0.000 claims 1
- VLZJRYAYKHJEAK-UHFFFAOYSA-N n-[3-[4-(hydroxycarbamoyl)phenyl]prop-2-ynyl]-5-(oxan-4-ylmethoxy)-1-benzofuran-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1C#CCNC(=O)C1=CC2=CC(OCC3CCOCC3)=CC=C2O1 VLZJRYAYKHJEAK-UHFFFAOYSA-N 0.000 claims 1
- JVOMSOLFCXKNJZ-UHFFFAOYSA-N n-[3-[4-(hydroxycarbamoyl)phenyl]prop-2-ynyl]-5-(oxan-4-yloxy)-1-benzofuran-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1C#CCNC(=O)C1=CC2=CC(OC3CCOCC3)=CC=C2O1 JVOMSOLFCXKNJZ-UHFFFAOYSA-N 0.000 claims 1
- YVGGUOSKVSEZPB-UHFFFAOYSA-N n-[3-[4-(hydroxycarbamoyl)phenyl]prop-2-ynyl]-5-methoxy-1h-indole-2-carboxamide Chemical compound C=1C2=CC(OC)=CC=C2NC=1C(=O)NCC#CC1=CC=C(C(=O)NO)C=C1 YVGGUOSKVSEZPB-UHFFFAOYSA-N 0.000 claims 1
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- 201000011549 stomach cancer Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- 230000007704 transition Effects 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
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- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
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- 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
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- 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
- C07C259/10—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 carbon atoms of six-membered aromatic rings
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- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/02—Carbamic acids; Salts of carbamic acids
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US49663803P | 2003-08-20 | 2003-08-20 |
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US (2) | US7368572B2 (de) |
EP (1) | EP1656348B1 (de) |
JP (1) | JP2007502838A (de) |
KR (1) | KR20060079798A (de) |
CN (1) | CN1795175A (de) |
AT (1) | ATE353319T1 (de) |
AU (1) | AU2004267085B2 (de) |
BR (1) | BRPI0410727A (de) |
CA (1) | CA2535350A1 (de) |
DE (1) | DE602004004665T2 (de) |
ES (1) | ES2282903T3 (de) |
MX (1) | MXPA05011286A (de) |
NO (1) | NO20061253L (de) |
NZ (1) | NZ542711A (de) |
PL (1) | PL1656348T4 (de) |
WO (1) | WO2005019174A1 (de) |
ZA (1) | ZA200507933B (de) |
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US20050137234A1 (en) * | 2003-12-19 | 2005-06-23 | Syrrx, Inc. | Histone deacetylase inhibitors |
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US20080248506A1 (en) * | 2004-10-07 | 2008-10-09 | Pharmacyclics, Inc. | Method of Monitoring Anti-Tumor Activity of an Hdac Inhibitor |
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 |
GB0510204D0 (en) | 2005-05-19 | 2005-06-22 | Chroma Therapeutics Ltd | Enzyme inhibitors |
CA2615105A1 (en) | 2005-07-14 | 2007-01-25 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
GB0619753D0 (en) | 2006-10-06 | 2006-11-15 | Chroma Therapeutics Ltd | Enzyme inhibitors |
US8962825B2 (en) | 2006-10-30 | 2015-02-24 | Glaxosmithkline Intellectual Property Development Limited | Hydroxamates as inhibitors of histone deacetylase |
US8796330B2 (en) * | 2006-12-19 | 2014-08-05 | Methylgene Inc. | Inhibitors of histone deacetylase and prodrugs thereof |
EP2079694B1 (de) | 2006-12-28 | 2017-03-01 | Rigel Pharmaceuticals, Inc. | N-substituierte heterocycloalkyloxybenzamidverbindungen und verfahren zu ihrer verwendung |
KR20090125209A (ko) | 2007-03-28 | 2009-12-03 | 산텐 세이야꾸 가부시키가이샤 | 히스톤 탈아세틸화 효소 저해 작용을 갖는 화합물을 유효 성분으로서 함유하는 안압 하강제 |
US20100285516A1 (en) * | 2007-04-13 | 2010-11-11 | Pharmacyclics, Inc. | Calcium flux as a pharmacoefficacy biomarker for inhibitors of histone deacetylase |
US20110015158A1 (en) | 2007-12-11 | 2011-01-20 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitors using metal binding moieties in combination with targeting moieties |
US20090270497A1 (en) * | 2008-04-24 | 2009-10-29 | Pharmacyclics, Inc. | Treatment of Non-Localized Inflammation with pan-HDAC Inhibitors |
RU2010153656A (ru) * | 2008-06-04 | 2012-07-20 | Амбрилиа Байофарма Инк. (Ca) | Ингибиторы интегразы вич из пиридоксина |
WO2010011700A2 (en) | 2008-07-23 | 2010-01-28 | The Brigham And Women's Hospital, Inc. | Treatment of cancers characterized by chromosomal rearrangement of the nut gene |
GB0903480D0 (en) | 2009-02-27 | 2009-04-08 | Chroma Therapeutics Ltd | Enzyme Inhibitors |
US8217079B2 (en) | 2010-03-26 | 2012-07-10 | Italfarmaco Spa | Method for treating Philadelphia-negative myeloproliferative syndromes |
CN102775368B (zh) * | 2011-05-10 | 2016-08-17 | 上海驺虞医药科技有限公司 | 一类噻唑类化合物及其制备方法和用途 |
CN102875479B (zh) * | 2012-10-24 | 2015-06-10 | 南京化工职业技术学院 | 喹唑啉二酮衍生物及其制备方法、其药物组合物及用途 |
CN103896911B (zh) * | 2014-03-06 | 2015-12-30 | 南方医科大学 | 2-(3,4-二甲氧基)苯甲酰基-5-(4-取代苯乙炔基)噻吩及其制备方法及应用 |
ITUB20155193A1 (it) | 2015-11-03 | 2017-05-03 | Italfarmaco Spa | Sospensioni orali di Givinostat fisicamente e chimicamente stabili |
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 |
KR20200143669A (ko) | 2018-01-17 | 2020-12-24 | 오리진 디스커버리 테크놀로지스 리미티드 | 항암제로서 치환된 알킬렌 화합물 |
CN113288888B (zh) * | 2021-05-28 | 2023-02-03 | 烟台邦杰生物科技有限公司 | 具有血管舒张活性的化合物 |
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GB9109007D0 (en) | 1991-04-26 | 1991-06-12 | Merck Sharp & Dohme | Therapeutic method |
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WO1999045009A1 (en) * | 1998-03-04 | 1999-09-10 | Bristol-Myers Squibb Company | Heterocyclo-substituted imidazopyrazine protein tyrosine kinase inhibitors |
US6211197B1 (en) | 1998-10-07 | 2001-04-03 | Merck Frosst Canada & Co. | Prostaglandin receptor ligands |
WO2001014331A2 (en) | 1999-08-24 | 2001-03-01 | Regents Of The University Of California | Non-quinoline inhibitors of malaria parasites |
CA2391952C (en) | 1999-11-23 | 2012-01-31 | Methylgene Inc. | Inhibitors of histone deacetylase |
BR0109469A (pt) | 2000-03-17 | 2003-04-29 | Bristol Myers Squibb Co | Compostos derivados de b-aminoácidos, composição farmacêutica, método para o tratamento ou prevenção de disfunções inflamatórias, método para o tratamento de condições ou doenças mediadas por mmps, tnf, aggrecanase ou uma combinação destes em mamìferos e uso do composto |
DE60130338T2 (de) | 2000-07-13 | 2008-05-29 | Merck Patent Gmbh | Chirale verbindungen ii |
US6897231B2 (en) | 2000-07-31 | 2005-05-24 | Signal Pharmaceuticals, Inc. | Indazole derivatives as JNK inhibitors and compositions and methods related thereto |
CA2423868C (en) | 2000-09-29 | 2011-06-07 | Prolifix Limited | Carbamic acid compounds comprising an amide linkage as hdac inhibitors |
WO2002030879A2 (en) * | 2000-09-29 | 2002-04-18 | Prolifix Limited | Carbamic acid compounds comprising a sulfonamide linkage as hdac inhibitors |
AU2001295986B2 (en) * | 2000-10-20 | 2006-08-17 | Eisai R&D Management Co., Ltd | Nitrogenous aromatic ring compounds |
TWI311133B (en) * | 2001-04-20 | 2009-06-21 | Eisai R&D Man Co Ltd | Carboxylic acid derivativeand the salt thereof |
WO2003000194A2 (en) | 2001-06-21 | 2003-01-03 | Pfizer Inc. | Thienopyridine and thienopyrimidine anticancer agents |
WO2003053941A2 (en) * | 2001-12-20 | 2003-07-03 | Bristol-Myers Squibb Company | Barbituric acid derivatives as inhibitors of tnf-alpha converting enzyme (tace) and/or matrix metalloproteinases |
WO2003070691A1 (fr) | 2002-02-21 | 2003-08-28 | Osaka Industrial Promotion Organization | Derive de n-hydroxycarboxamide |
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2004
- 2004-08-19 WO PCT/US2004/027053 patent/WO2005019174A1/en active IP Right Grant
- 2004-08-19 KR KR1020067002848A patent/KR20060079798A/ko not_active Application Discontinuation
- 2004-08-19 NZ NZ542711A patent/NZ542711A/en unknown
- 2004-08-19 CA CA002535350A patent/CA2535350A1/en not_active Abandoned
- 2004-08-19 ZA ZA200507933A patent/ZA200507933B/en unknown
- 2004-08-19 BR BRPI0410727-6A patent/BRPI0410727A/pt not_active Application Discontinuation
- 2004-08-19 MX MXPA05011286A patent/MXPA05011286A/es active IP Right Grant
- 2004-08-19 JP JP2006524072A patent/JP2007502838A/ja active Pending
- 2004-08-19 PL PL04781685T patent/PL1656348T4/pl unknown
- 2004-08-19 EP EP04781685A patent/EP1656348B1/de active Active
- 2004-08-19 AT AT04781685T patent/ATE353319T1/de not_active IP Right Cessation
- 2004-08-19 ES ES04781685T patent/ES2282903T3/es active Active
- 2004-08-19 DE DE602004004665T patent/DE602004004665T2/de active Active
- 2004-08-19 US US10/922,119 patent/US7368572B2/en not_active Expired - Fee Related
- 2004-08-19 CN CNA2004800141964A patent/CN1795175A/zh active Pending
- 2004-08-19 AU AU2004267085A patent/AU2004267085B2/en not_active Ceased
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2006
- 2006-03-17 NO NO20061253A patent/NO20061253L/no not_active Application Discontinuation
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2008
- 2008-02-07 US US12/027,903 patent/US20080139547A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
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US20080139547A1 (en) | 2008-06-12 |
DE602004004665D1 (en) | 2007-03-22 |
EP1656348A1 (de) | 2006-05-17 |
US7368572B2 (en) | 2008-05-06 |
NZ542711A (en) | 2008-03-28 |
CN1795175A (zh) | 2006-06-28 |
US20050131018A1 (en) | 2005-06-16 |
DE602004004665T2 (de) | 2008-01-03 |
ATE353319T1 (de) | 2007-02-15 |
AU2004267085A1 (en) | 2005-03-03 |
AU2004267085B2 (en) | 2010-09-16 |
MXPA05011286A (es) | 2006-01-24 |
EP1656348B1 (de) | 2007-02-07 |
JP2007502838A (ja) | 2007-02-15 |
NO20061253L (no) | 2006-05-18 |
ES2282903T3 (es) | 2007-10-16 |
PL1656348T3 (pl) | 2007-07-31 |
BRPI0410727A (pt) | 2006-06-20 |
KR20060079798A (ko) | 2006-07-06 |
WO2005019174A1 (en) | 2005-03-03 |
CA2535350A1 (en) | 2005-03-03 |
PL1656348T4 (pl) | 2007-07-31 |
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