ZA200407232B - Sulfonyl-derivatives as novel inhibitors of histone deacetylase. - Google Patents
Sulfonyl-derivatives as novel inhibitors of histone deacetylase. Download PDFInfo
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- ZA200407232B ZA200407232B ZA200407232A ZA200407232A ZA200407232B ZA 200407232 B ZA200407232 B ZA 200407232B ZA 200407232 A ZA200407232 A ZA 200407232A ZA 200407232 A ZA200407232 A ZA 200407232A ZA 200407232 B ZA200407232 B ZA 200407232B
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- ZA
- South Africa
- Prior art keywords
- galkyl
- salkyl
- aminoc
- 4alkyl
- amino
- Prior art date
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- 102000003964 Histone deacetylase Human genes 0.000 title claims description 25
- 108090000353 Histone deacetylase Proteins 0.000 title claims description 25
- 239000003112 inhibitor Substances 0.000 title description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 113
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 108
- -1 methylimidazolyl Chemical group 0.000 claims description 68
- 150000001875 compounds Chemical class 0.000 claims description 65
- 229910052739 hydrogen Inorganic materials 0.000 claims description 64
- 239000001257 hydrogen Substances 0.000 claims description 64
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 150000002431 hydrogen Chemical class 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 125000004076 pyridyl group Chemical group 0.000 claims description 25
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 23
- 125000002541 furyl group Chemical group 0.000 claims description 23
- 125000001544 thienyl group Chemical group 0.000 claims description 23
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 16
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- 238000000034 method Methods 0.000 claims description 12
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- 125000002757 morpholinyl group Chemical group 0.000 claims description 10
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- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 7
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- 239000003276 histone deacetylase inhibitor Substances 0.000 claims description 5
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- 125000001475 halogen functional group Chemical group 0.000 claims 16
- 238000004519 manufacturing process Methods 0.000 claims 4
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- 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 2
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- 239000003937 drug carrier Substances 0.000 claims 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims 2
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- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 claims 1
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 claims 1
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- 239000003054 catalyst Substances 0.000 claims 1
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- 238000001514 detection method Methods 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 description 25
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/402—1-aryl substituted, e.g. piretanide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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ZA200407234A ZA200407234B (en) | 2002-03-13 | 2004-09-09 | New inhibitors of histone deacetylase. |
ZA200407232A ZA200407232B (en) | 2002-03-13 | 2004-09-09 | Sulfonyl-derivatives as novel inhibitors of histone deacetylase. |
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ZA200407237A ZA200407237B (en) | 2002-03-13 | 2004-09-09 | Piperazinyl-, piperidinyl- and morpholinyl-derivatives as novel inhibitors of histone deacetylase. |
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JP (4) | JP4644428B2 (fr) |
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US6951862B2 (en) | 1998-06-30 | 2005-10-04 | Neuromed Technologies, Inc. | Calcium channel blockers comprising two benzhydril moieties |
US7186726B2 (en) | 1998-06-30 | 2007-03-06 | Neuromed Pharmaceuticals Ltd. | Preferentially substituted calcium channel blockers |
AU2002327627B2 (en) | 2001-09-14 | 2006-09-14 | Methylgene Inc. | Inhibitors of histone deacetylase |
US7868204B2 (en) | 2001-09-14 | 2011-01-11 | Methylgene Inc. | Inhibitors of histone deacetylase |
US6897220B2 (en) | 2001-09-14 | 2005-05-24 | Methylgene, Inc. | Inhibitors of histone deacetylase |
US7390813B1 (en) | 2001-12-21 | 2008-06-24 | Xenon Pharmaceuticals Inc. | Pyridylpiperazines and aminonicotinamides and their use as therapeutic agents |
EP1485348B1 (fr) | 2002-03-13 | 2008-06-11 | Janssen Pharmaceutica N.V. | Derives carbonylamino utilises en tant que nouveaux inhibiteurs d'histone deacetylase |
CN100445276C (zh) * | 2002-03-13 | 2008-12-24 | 詹森药业有限公司 | 用作组蛋白去乙酰酶抑制剂的磺酰基衍生物 |
US7767679B2 (en) | 2002-03-13 | 2010-08-03 | Janssen Pharmaceutica N.V. | Sulfonylamino-derivatives as novel inhibitors of histone deacetylase |
WO2003076438A1 (fr) * | 2002-03-13 | 2003-09-18 | Janssen Pharmaceutica N.V. | Derives piperazinyl-, piperidinyl- et morpholinyl- utilises en tant que nouveaux inhibiteurs d'histone deacetylase |
EA007272B1 (ru) * | 2002-03-13 | 2006-08-25 | Янссен Фармацевтика Н. В. | Новые ингибиторы гистондеацетилазы |
TWI319387B (en) | 2002-04-05 | 2010-01-11 | Astrazeneca Ab | Benzamide derivatives |
EP1547617B1 (fr) * | 2002-08-20 | 2010-04-28 | Astellas Pharma Inc. | Inhibiteur de degradation de la matrice extracellulaire du cartilage arthrodial |
WO2004024710A1 (fr) * | 2002-09-13 | 2004-03-25 | Glaxo Group Limited | Composes a base d'uree, actifs en tant qu'antagonistes du recepteur de la vanilloide et utilises pour traiter les douleurs |
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 |
WO2004052292A2 (fr) * | 2002-12-06 | 2004-06-24 | University Of South Florida | Amelioration de l'apoptose induite par trail au moyen d'un inhibiteur de l'histone deacetylase |
PL1622569T3 (pl) | 2003-04-24 | 2016-06-30 | Incyte Holdings Corp | Pochodne aza spiro alkanów jako inhibitory metaloproteaz |
WO2005011654A2 (fr) | 2003-07-29 | 2005-02-10 | Xenon Pharmaceuticals Inc. | Derives de pyridyle et utilisation de ceux-ci en tant qu'agents therapeutiques |
AU2004261267B9 (en) | 2003-07-30 | 2009-04-09 | Xenon Pharmaceuticals Inc. | Pyridyl derivatives and their use as therapeutic agents |
BRPI0412348A (pt) | 2003-07-30 | 2006-09-05 | Xenon Pharmaceuticals Inc | derivados de piperazina e seu uso como agentes terapêuticos |
JP4831577B2 (ja) | 2003-07-30 | 2011-12-07 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | ピリダジン誘導体および治療剤としての用途 |
ES2568769T3 (es) | 2003-07-30 | 2016-05-04 | Xenon Pharmaceuticals Inc. | Derivados de piperazina y su uso como agentes terapéuticos |
US7754711B2 (en) | 2003-07-30 | 2010-07-13 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
WO2005030705A1 (fr) | 2003-09-24 | 2005-04-07 | Methylgene, Inc. | Inhibiteurs d'histone deacetylase |
US7253204B2 (en) | 2004-03-26 | 2007-08-07 | Methylgene Inc. | Inhibitors of histone deacetylase |
JP2007532492A (ja) * | 2004-04-09 | 2007-11-15 | ニューロメッド ファーマシューティカルズ リミテッド | カルシウムチャネルブロッカーとしてのジアリールアミン誘導体 |
WO2005110413A2 (fr) | 2004-05-19 | 2005-11-24 | Solvay Pharmaceuticals Gmbh | Medicaments contenant des n-sulfamoyl-n'-arylpiperazines utilises pour la prophylaxie ou le traitement de l'obesite et des pathologies apparentees |
GB0412072D0 (en) * | 2004-05-28 | 2004-06-30 | Syngenta Participations Ag | Chemical compounds |
CA2566525A1 (fr) | 2004-06-14 | 2005-12-22 | F. Hoffmann-La Roche Ag | Derives de thiophene, leur fabrication et leur utilisation comme agents pharmaceutiques |
CA2566515A1 (fr) | 2004-06-14 | 2005-12-22 | F. Hoffmann-La Roche Ag | Derives d'acide hydroxamique thiophene et leur utilisation comme inhibiteurs hdac |
EP1781639B1 (fr) * | 2004-07-28 | 2012-01-25 | Janssen Pharmaceutica NV | Derives d'indolyl alkyl amine substitues utilises en tant que nouveaux inhibiteurs d'histone deacetylase |
ME01058B (fr) * | 2004-07-28 | 2012-10-20 | Janssen Pharmaceutica Nv | Derives de piperazine de propenyle substituee comme nouveaux inhibiteurs de l'histone deacetylase |
EP1776358B1 (fr) * | 2004-07-28 | 2009-05-27 | Janssen Pharmaceutica N.V. | Derivés substitués de propenyl piperazine comme nouveaux inhibiteurs de histone deacetylase |
MX2007001634A (es) * | 2004-08-11 | 2007-04-23 | Kyorin Seiyaku Kk | Nuevo derivado de acido amino benzoico ciclico. |
TW200626155A (en) | 2004-09-20 | 2006-08-01 | Xenon Pharmaceuticals Inc | Heterocyclic derivatives and their use as therapeutic agents |
AR051095A1 (es) | 2004-09-20 | 2006-12-20 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso comoinhibidores de la estearoil-coa desaturasa |
AU2005329423A1 (en) | 2004-09-20 | 2006-09-28 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
CN101083982A (zh) | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 用于治疗硬脂酰CoA去饱和酶介导的疾病的杂环衍生物 |
WO2006034279A1 (fr) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Derives heterocycliques et leur utilisation comme agents therapeutiques |
BRPI0515478A (pt) | 2004-09-20 | 2008-07-22 | Xenon Pharmaceuticals Inc | derivados heterocìclicos e seu uso como mediadores de estearoil-coa-desaturase |
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