ES2291308T3 - Derivados de aminofenoxiacetamida y composicion farmaceutica que contiene los mismos. - Google Patents
Derivados de aminofenoxiacetamida y composicion farmaceutica que contiene los mismos. Download PDFInfo
- Publication number
- ES2291308T3 ES2291308T3 ES01921835T ES01921835T ES2291308T3 ES 2291308 T3 ES2291308 T3 ES 2291308T3 ES 01921835 T ES01921835 T ES 01921835T ES 01921835 T ES01921835 T ES 01921835T ES 2291308 T3 ES2291308 T3 ES 2291308T3
- Authority
- ES
- Spain
- Prior art keywords
- group
- compound
- aminophenoxyacetamide
- substituted
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- AHZPJIGLXKMUCO-UHFFFAOYSA-N 2-amino-2-phenoxyacetamide Chemical class NC(=O)C(N)OC1=CC=CC=C1 AHZPJIGLXKMUCO-UHFFFAOYSA-N 0.000 title claims description 36
- 239000008194 pharmaceutical composition Substances 0.000 title description 4
- 125000005843 halogen group Chemical group 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 208000014644 Brain disease Diseases 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 102000004169 proteins and genes Human genes 0.000 claims description 12
- 108090000623 proteins and genes Proteins 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 208000024827 Alzheimer disease Diseases 0.000 claims description 8
- 210000004556 brain Anatomy 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 230000006698 induction Effects 0.000 claims description 7
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 6
- 206010008118 cerebral infarction Diseases 0.000 claims description 6
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
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- 239000004480 active ingredient Substances 0.000 claims description 5
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- 229940079593 drug Drugs 0.000 claims description 5
- 230000006872 improvement Effects 0.000 claims description 5
- 208000020658 intracerebral hemorrhage Diseases 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 206010065559 Cerebral arteriosclerosis Diseases 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- 206010039966 Senile dementia Diseases 0.000 claims description 4
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 201000005851 intracranial arteriosclerosis Diseases 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
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- 230000002708 enhancing effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 37
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 abstract description 6
- 239000001301 oxygen Substances 0.000 abstract description 6
- 238000002485 combustion reaction Methods 0.000 abstract 4
- 239000007789 gas Substances 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- 239000010849 combustible waste Substances 0.000 abstract 1
- 239000002826 coolant Substances 0.000 abstract 1
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- 150000001875 compounds Chemical class 0.000 description 193
- -1 methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy Chemical group 0.000 description 49
- 238000012360 testing method Methods 0.000 description 47
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 230000000324 neuroprotective effect Effects 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 230000000694 effects Effects 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
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- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
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- WUUGFSXJNOTRMR-IOSLPCCCSA-N 5'-S-methyl-5'-thioadenosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CSC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 WUUGFSXJNOTRMR-IOSLPCCCSA-N 0.000 description 13
- 229930195712 glutamate Natural products 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000012442 inert solvent Substances 0.000 description 11
- 235000018102 proteins Nutrition 0.000 description 11
- 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 108091008794 FGF receptors Proteins 0.000 description 10
- 102000044168 Fibroblast Growth Factor Receptor Human genes 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- XVQWECOXNZBRRU-UHFFFAOYSA-N N-[2-(4-amino-2,3,5,6-tetramethylphenoxy)-1-methylpiperidin-4-yl]propanamide Chemical compound CCC(=O)NC1CCN(C)C(C1)Oc1c(C)c(C)c(N)c(C)c1C XVQWECOXNZBRRU-UHFFFAOYSA-N 0.000 description 9
- 230000004913 activation Effects 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 238000011534 incubation Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 230000004083 survival effect Effects 0.000 description 9
- CQHRFKKIHUKFFK-MMOCMJAISA-N 2-(4-amino-2,3,5,6-tetramethylphenoxy)-n-methyl-n-[1-[[(1r,2r)-2-phenylcyclopropyl]methyl]piperidin-4-yl]propanamide Chemical compound C1CN(C[C@H]2[C@@H](C2)C=2C=CC=CC=2)CCC1N(C)C(=O)C(C)OC1=C(C)C(C)=C(N)C(C)=C1C CQHRFKKIHUKFFK-MMOCMJAISA-N 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- 102000005701 Calcium-Binding Proteins Human genes 0.000 description 8
- 108010045403 Calcium-Binding Proteins Proteins 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 125000001309 chloro group Chemical group Cl* 0.000 description 8
- 210000002569 neuron Anatomy 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 7
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- 230000004770 neurodegeneration Effects 0.000 description 7
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- 239000000243 solution Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- 230000001067 neuroprotector Effects 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- YDRFQQVPXSSBGA-UHFFFAOYSA-N 2-(4-amino-2,3,5,6-tetramethylphenoxy)-n-[1-[(4-cyanophenyl)methyl]piperidin-4-yl]-n-methylacetamide Chemical compound CC=1C(C)=C(N)C(C)=C(C)C=1OCC(=O)N(C)C(CC1)CCN1CC1=CC=C(C#N)C=C1 YDRFQQVPXSSBGA-UHFFFAOYSA-N 0.000 description 5
- WOLVXYYAHYZXOQ-UHFFFAOYSA-N 2-(4-amino-2,3,5,6-tetramethylphenoxy)-n-methyl-n-(1-phenacylpiperidin-4-yl)acetamide Chemical compound CC=1C(C)=C(N)C(C)=C(C)C=1OCC(=O)N(C)C(CC1)CCN1CC(=O)C1=CC=CC=C1 WOLVXYYAHYZXOQ-UHFFFAOYSA-N 0.000 description 5
- IMMXUJRVUKFHAJ-UHFFFAOYSA-N 2-piperidin-4-ylpropanamide Chemical compound NC(=O)C(C)C1CCNCC1 IMMXUJRVUKFHAJ-UHFFFAOYSA-N 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
- 101150021185 FGF gene Proteins 0.000 description 5
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
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- NHVWISFIIPIKSZ-UHFFFAOYSA-N tert-butyl n-[4-(methylamino)piperidin-1-yl]carbamate Chemical compound CNC1CCN(NC(=O)OC(C)(C)C)CC1 NHVWISFIIPIKSZ-UHFFFAOYSA-N 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
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- PSOHDCHTEDEPTH-UHFFFAOYSA-N 2-(2-amino-3,4,5,6-tetramethylphenoxy)-n-methyl-n-(1-phenacylpiperidin-4-yl)acetamide Chemical compound CC=1C(C)=C(C)C(C)=C(N)C=1OCC(=O)N(C)C(CC1)CCN1CC(=O)C1=CC=CC=C1 PSOHDCHTEDEPTH-UHFFFAOYSA-N 0.000 description 4
- PQIBKPSHVSPOOW-UHFFFAOYSA-N 2-(3-amino-2,4,5,6-tetramethylphenoxy)-n-methyl-n-[1-(2-phenylethyl)piperidin-4-yl]acetamide Chemical compound CC=1C(C)=C(C)C(N)=C(C)C=1OCC(=O)N(C)C(CC1)CCN1CCC1=CC=CC=C1 PQIBKPSHVSPOOW-UHFFFAOYSA-N 0.000 description 4
- OISJBMQWFVZTLU-UHFFFAOYSA-N 2-(3-amino-2,4,6-trimethylanilino)-n-[1-(4-fluorophenyl)piperidin-4-yl]-n-methylacetamide Chemical compound CC=1C=C(C)C(N)=C(C)C=1NCC(=O)N(C)C(CC1)CCN1C1=CC=C(F)C=C1 OISJBMQWFVZTLU-UHFFFAOYSA-N 0.000 description 4
- LULWRQOJPGCJQR-UHFFFAOYSA-N 2-(4-amino-2,3,5,6-tetramethylanilino)-n-[1-(1,3-benzothiazol-2-yl)piperidin-4-yl]-n-methylacetamide Chemical compound C1CN(C=2SC3=CC=CC=C3N=2)CCC1N(C)C(=O)CNC1=C(C)C(C)=C(N)C(C)=C1C LULWRQOJPGCJQR-UHFFFAOYSA-N 0.000 description 4
- ZIBVYDHPNWVHJL-UHFFFAOYSA-N 2-(4-amino-2,3,5,6-tetramethylanilino)-n-[1-(4-fluorophenyl)piperidin-4-yl]-n-methylacetamide Chemical compound CC=1C(C)=C(N)C(C)=C(C)C=1NCC(=O)N(C)C(CC1)CCN1C1=CC=C(F)C=C1 ZIBVYDHPNWVHJL-UHFFFAOYSA-N 0.000 description 4
- JQUASWQGXZQJJY-UHFFFAOYSA-N 2-(4-amino-2,3,5,6-tetramethylanilino)-n-methyl-n-[1-(4-phenylphenyl)piperidin-4-yl]propanamide Chemical compound C1CN(C=2C=CC(=CC=2)C=2C=CC=CC=2)CCC1N(C)C(=O)C(C)NC1=C(C)C(C)=C(N)C(C)=C1C JQUASWQGXZQJJY-UHFFFAOYSA-N 0.000 description 4
- UQGCIEYGWAFZHZ-UHFFFAOYSA-N 2-(4-amino-2,3,5,6-tetramethylphenoxy)-n-(1-benzoylpiperidin-4-yl)-n-methylacetamide Chemical compound CC=1C(C)=C(N)C(C)=C(C)C=1OCC(=O)N(C)C(CC1)CCN1C(=O)C1=CC=CC=C1 UQGCIEYGWAFZHZ-UHFFFAOYSA-N 0.000 description 4
- XPGDCWMZZUVRGW-UHFFFAOYSA-N 2-(4-amino-2,3,5,6-tetramethylphenoxy)-n-(1-butylpiperidin-4-yl)-n-methylacetamide Chemical compound C1CN(CCCC)CCC1N(C)C(=O)COC1=C(C)C(C)=C(N)C(C)=C1C XPGDCWMZZUVRGW-UHFFFAOYSA-N 0.000 description 4
- SDYHZOJCWKPIOX-UHFFFAOYSA-N 2-(4-amino-2,3,5,6-tetramethylphenoxy)-n-(1-butylpiperidin-4-yl)-n-methylpropanamide Chemical compound C1CN(CCCC)CCC1N(C)C(=O)C(C)OC1=C(C)C(C)=C(N)C(C)=C1C SDYHZOJCWKPIOX-UHFFFAOYSA-N 0.000 description 4
- QWAOSKYULAXJST-UHFFFAOYSA-N 2-(4-amino-2,3,5,6-tetramethylphenoxy)-n-[1-[2-(2-hydroxy-2-phenylethoxy)ethyl]piperidin-4-yl]-n-methylacetamide Chemical compound CC=1C(C)=C(N)C(C)=C(C)C=1OCC(=O)N(C)C(CC1)CCN1CCOCC(O)C1=CC=CC=C1 QWAOSKYULAXJST-UHFFFAOYSA-N 0.000 description 4
- YAXXGVFPJRLNEF-UHFFFAOYSA-N 2-(4-amino-2,3,5,6-tetramethylphenoxy)-n-methyl-n-[1-[2-(n-methylanilino)-2-oxoethyl]piperidin-4-yl]propanamide Chemical compound C1CN(CC(=O)N(C)C=2C=CC=CC=2)CCC1N(C)C(=O)C(C)OC1=C(C)C(C)=C(N)C(C)=C1C YAXXGVFPJRLNEF-UHFFFAOYSA-N 0.000 description 4
- RIGOKHDXWCNWEY-UHFFFAOYSA-N 2-(4-amino-2,3,5-trimethylphenoxy)-n-[1-(4-fluorophenyl)piperidin-4-yl]-n-methylacetamide Chemical compound C=1C(C)=C(N)C(C)=C(C)C=1OCC(=O)N(C)C(CC1)CCN1C1=CC=C(F)C=C1 RIGOKHDXWCNWEY-UHFFFAOYSA-N 0.000 description 4
- MSXFYGVHHAEESK-UHFFFAOYSA-N 2-[4-[[2-(4-amino-2,3,5,6-tetramethylphenoxy)acetyl]-methylamino]piperidin-1-yl]-n-phenylacetamide Chemical compound CC=1C(C)=C(N)C(C)=C(C)C=1OCC(=O)N(C)C(CC1)CCN1CC(=O)NC1=CC=CC=C1 MSXFYGVHHAEESK-UHFFFAOYSA-N 0.000 description 4
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
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- IHSIFALCHVNSNY-UHFFFAOYSA-N tert-butyl n-(4-amino-3,5-dichlorophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(Cl)=C(N)C(Cl)=C1 IHSIFALCHVNSNY-UHFFFAOYSA-N 0.000 description 1
- GVWPULGIVBRUMS-UHFFFAOYSA-N tert-butyl n-(4-amino-5-methoxy-2-methylphenyl)carbamate Chemical compound COC1=CC(NC(=O)OC(C)(C)C)=C(C)C=C1N GVWPULGIVBRUMS-UHFFFAOYSA-N 0.000 description 1
- VZMBTSBTKXWMRP-UHFFFAOYSA-N tert-butyl n-(4-hydroxy-2,3,5,6-tetramethylphenyl)carbamate Chemical compound CC1=C(C)C(NC(=O)OC(C)(C)C)=C(C)C(C)=C1O VZMBTSBTKXWMRP-UHFFFAOYSA-N 0.000 description 1
- GNLWEQIJQBMIQP-UHFFFAOYSA-N tert-butyl n-(4-hydroxy-2,3,5-trimethylphenyl)carbamate Chemical compound CC1=CC(NC(=O)OC(C)(C)C)=C(C)C(C)=C1O GNLWEQIJQBMIQP-UHFFFAOYSA-N 0.000 description 1
- JEVIOGKIJOREOJ-UHFFFAOYSA-N tert-butyl n-(4-hydroxy-2,3,6-trimethylphenyl)carbamate Chemical compound CC1=CC(O)=C(C)C(C)=C1NC(=O)OC(C)(C)C JEVIOGKIJOREOJ-UHFFFAOYSA-N 0.000 description 1
- MDGMIJLHJMGQPK-UHFFFAOYSA-N tert-butyl n-(4-hydroxy-2,3-dimethylphenyl)carbamate Chemical compound CC1=C(O)C=CC(NC(=O)OC(C)(C)C)=C1C MDGMIJLHJMGQPK-UHFFFAOYSA-N 0.000 description 1
- HYAXOCCNXTUFSN-UHFFFAOYSA-N tert-butyl n-(4-hydroxy-2,5-dimethylphenyl)carbamate Chemical compound CC1=CC(NC(=O)OC(C)(C)C)=C(C)C=C1O HYAXOCCNXTUFSN-UHFFFAOYSA-N 0.000 description 1
- YRQMBQUMJFVZLF-UHFFFAOYSA-N tert-butyl n-(4-hydroxyphenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(O)C=C1 YRQMBQUMJFVZLF-UHFFFAOYSA-N 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 201000010875 transient cerebral ischemia Diseases 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- PUVAFTRIIUSGLK-UHFFFAOYSA-M trimethyl(oxiran-2-ylmethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1CO1 PUVAFTRIIUSGLK-UHFFFAOYSA-M 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000001262 western blot Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—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
- 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
-
- 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
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—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
- 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
- C07D417/06—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Physical Education & Sports Medicine (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000112100 | 2000-04-13 | ||
| JP2000-112100 | 2000-04-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2291308T3 true ES2291308T3 (es) | 2008-03-01 |
Family
ID=18624324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES01921835T Expired - Lifetime ES2291308T3 (es) | 2000-04-13 | 2001-04-13 | Derivados de aminofenoxiacetamida y composicion farmaceutica que contiene los mismos. |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US7067533B2 (enExample) |
| EP (1) | EP1228367B1 (enExample) |
| JP (1) | JP2004501079A (enExample) |
| KR (1) | KR100853968B1 (enExample) |
| CN (1) | CN1264821C (enExample) |
| AT (1) | ATE374366T1 (enExample) |
| AU (1) | AU784930B2 (enExample) |
| CA (1) | CA2370487A1 (enExample) |
| DE (1) | DE60130628T2 (enExample) |
| ES (1) | ES2291308T3 (enExample) |
| HU (1) | HUP0203383A3 (enExample) |
| WO (1) | WO2001079170A2 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030186963A1 (en) | 2001-09-14 | 2003-10-02 | Dorwald Florencio Zaragoza | Substituted piperidines |
| JP2005508907A (ja) * | 2001-09-14 | 2005-04-07 | ノボ ノルディスク アクティーゼルスカブ | ヒスタミンｈ３受容体に選択的に結合する置換されたピペリジン |
| AU2006333522A1 (en) * | 2005-12-21 | 2007-07-12 | Decode Genetics, Ehf. | Biaryl nitrogen heterocycle inhibitors of LTA4H for treating inflammation |
| DE102005062990A1 (de) | 2005-12-28 | 2007-07-05 | Grünenthal GmbH | Substituierte Thiazole und ihre Verwendung zur Herstellung von Arzneimitteln |
| SI2151439T1 (sl) * | 2007-04-27 | 2014-05-30 | Daiichi Sankyo Company, Limited | Nitrogeniran aromatski derivat s 6-členskim obročem in farmacevtsko sredstvo, ki obsega ta derivat |
| US20180305334A1 (en) * | 2015-10-14 | 2018-10-25 | Aquinnah Pharmaceuticals, Inc. | Compounds, compositions and methods of use against stress granules |
| KR20190015748A (ko) | 2016-06-08 | 2019-02-14 | 글락소스미스클라인 인털렉츄얼 프로퍼티 디벨로프먼트 리미티드 | Atf4 경로 억제제로서의 화학적 화합물 |
| CN111285820A (zh) * | 2018-12-07 | 2020-06-16 | 成都康弘药业集团股份有限公司 | 一种枸橼酸莫沙必利有关物质及其制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW204411B (enExample) * | 1991-06-05 | 1993-04-21 | Tokyo Electron Co Ltd | |
| EP0982026B1 (en) | 1998-08-18 | 2006-05-17 | F. Hoffmann-La Roche Ag | Use of aryl-cyclohexylamine derivatives in the manufacture of NMDA receptor blockers |
| CN1198613C (zh) | 1998-10-16 | 2005-04-27 | 第一三得利制药株式会社 | 氨基苯氧基乙酸衍生物和含有它们的药用组合物 |
-
2001
- 2001-04-13 AU AU48762/01A patent/AU784930B2/en not_active Ceased
- 2001-04-13 EP EP01921835A patent/EP1228367B1/en not_active Expired - Lifetime
- 2001-04-13 JP JP2001576772A patent/JP2004501079A/ja not_active Abandoned
- 2001-04-13 AT AT01921835T patent/ATE374366T1/de not_active IP Right Cessation
- 2001-04-13 WO PCT/JP2001/003198 patent/WO2001079170A2/en not_active Ceased
- 2001-04-13 DE DE60130628T patent/DE60130628T2/de not_active Expired - Fee Related
- 2001-04-13 KR KR1020017015979A patent/KR100853968B1/ko not_active Expired - Fee Related
- 2001-04-13 CN CNB018009085A patent/CN1264821C/zh not_active Expired - Fee Related
- 2001-04-13 HU HU0203383A patent/HUP0203383A3/hu unknown
- 2001-04-13 ES ES01921835T patent/ES2291308T3/es not_active Expired - Lifetime
- 2001-04-13 US US10/009,566 patent/US7067533B2/en not_active Expired - Fee Related
- 2001-04-13 CA CA002370487A patent/CA2370487A1/en not_active Abandoned
-
2006
- 2006-01-24 US US11/337,664 patent/US20060178401A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN1264821C (zh) | 2006-07-19 |
| DE60130628T2 (de) | 2008-07-10 |
| HUP0203383A3 (en) | 2003-11-28 |
| DE60130628D1 (de) | 2007-11-08 |
| US7067533B2 (en) | 2006-06-27 |
| ATE374366T1 (de) | 2007-10-15 |
| US20060178401A1 (en) | 2006-08-10 |
| KR20020016830A (ko) | 2002-03-06 |
| AU784930B2 (en) | 2006-08-03 |
| US20030139447A1 (en) | 2003-07-24 |
| WO2001079170A3 (en) | 2002-06-13 |
| CN1449493A (zh) | 2003-10-15 |
| CA2370487A1 (en) | 2001-10-25 |
| AU4876201A (en) | 2001-10-30 |
| KR100853968B1 (ko) | 2008-08-25 |
| EP1228367A2 (en) | 2002-08-07 |
| HUP0203383A2 (hu) | 2003-02-28 |
| WO2001079170A2 (en) | 2001-10-25 |
| JP2004501079A (ja) | 2004-01-15 |
| EP1228367B1 (en) | 2007-09-26 |
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