KR20040029429A - 이속사졸로피리디논 및 파킨슨병의 치료에 있어서 그의용도 - Google Patents
이속사졸로피리디논 및 파킨슨병의 치료에 있어서 그의용도 Download PDFInfo
- Publication number
- KR20040029429A KR20040029429A KR10-2004-7002124A KR20047002124A KR20040029429A KR 20040029429 A KR20040029429 A KR 20040029429A KR 20047002124 A KR20047002124 A KR 20047002124A KR 20040029429 A KR20040029429 A KR 20040029429A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- alkylamino
- alkoxy
- phenyl
- compound
- 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.)
- Ceased
Links
- 208000018737 Parkinson disease Diseases 0.000 title claims abstract description 14
- WJLKGZPFGUBCPD-UHFFFAOYSA-N 1h-[1,2]oxazolo[4,3-b]pyridin-3-one Chemical class C1=CN=C2C(=O)ONC2=C1 WJLKGZPFGUBCPD-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 238000000034 method Methods 0.000 claims abstract description 17
- 239000003814 drug Substances 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- -1 and Chemical group 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 239000012458 free base Substances 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000005605 benzo group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 229940088679 drug related substance Drugs 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- KPXIVOYDTAKEBC-UHFFFAOYSA-N 6-[4-[(dimethylamino)methyl]phenyl]-3-phenyl-5H-[1,2]oxazolo[4,5-c]pyridin-4-one Chemical compound C1=CC(CN(C)C)=CC=C1C(NC1=O)=CC2=C1C(C=1C=CC=CC=1)=NO2 KPXIVOYDTAKEBC-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000008024 pharmaceutical diluent Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 238000001819 mass spectrum Methods 0.000 description 39
- 239000007787 solid Substances 0.000 description 34
- 239000000243 solution Substances 0.000 description 26
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 description 24
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 20
- 239000003795 chemical substances by application Substances 0.000 description 19
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 18
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 16
- 101150026563 NR4A2 gene Proteins 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 229960003638 dopamine Drugs 0.000 description 8
- 150000002825 nitriles Chemical class 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 238000003556 assay Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- LWRSYTXEQUUTKW-UHFFFAOYSA-N 2,4-dimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1 LWRSYTXEQUUTKW-UHFFFAOYSA-N 0.000 description 4
- CHNWMDMUDPRLQA-UHFFFAOYSA-N 2h-[1,2]oxazolo[4,5-c]pyridin-4-one Chemical class O=C1N=CC=C2ONC=C12 CHNWMDMUDPRLQA-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 108700008625 Reporter Genes Proteins 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 210000001259 mesencephalon Anatomy 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- PENHKTNQUJMHIR-UHFFFAOYSA-N 5-methyl-3-phenyl-1,2-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=C(C)ON=C1C1=CC=CC=C1 PENHKTNQUJMHIR-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- 125000004849 alkoxymethyl group Chemical group 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 108020001756 ligand binding domains Proteins 0.000 description 3
- DCKOQOHEZADEJX-UHFFFAOYSA-N n,5-dimethyl-3-phenyl-1,2-oxazole-4-carboxamide Chemical compound CNC(=O)C1=C(C)ON=C1C1=CC=CC=C1 DCKOQOHEZADEJX-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IKDMREAHMCMBIG-UHFFFAOYSA-N 1,3-dioxole-4-carbonitrile Chemical compound N#CC1=COCO1 IKDMREAHMCMBIG-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- SZENQRLSNAOEPP-UHFFFAOYSA-N 2-[(4-methylpiperazin-1-yl)methyl]benzonitrile Chemical compound C1CN(C)CCN1CC1=CC=CC=C1C#N SZENQRLSNAOEPP-UHFFFAOYSA-N 0.000 description 2
- PPUUWHCQKUSMQV-UHFFFAOYSA-N 6-[4-(2-hydroxyethoxymethyl)phenyl]-5-methyl-3-phenyl-[1,2]oxazolo[4,5-c]pyridin-4-one Chemical compound C1=2C(=O)N(C)C(C=3C=CC(COCCO)=CC=3)=CC=2ON=C1C1=CC=CC=C1 PPUUWHCQKUSMQV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- FEIOASZZURHTHB-UHFFFAOYSA-N Methyl-p-formylbenzoate Natural products COC(=O)C1=CC=C(C=O)C=C1 FEIOASZZURHTHB-UHFFFAOYSA-N 0.000 description 2
- RQLPYIHNISDJAP-UHFFFAOYSA-N O=C1N=CC=C2NOC=C12 Chemical class O=C1N=CC=C2NOC=C12 RQLPYIHNISDJAP-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 238000011097 chromatography purification Methods 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- DQNUZURLZCIRLZ-UHFFFAOYSA-N n,3-dimethyl-5-phenyl-1,2-oxazole-4-carboxamide Chemical compound CC1=NOC(C=2C=CC=CC=2)=C1C(=O)NC DQNUZURLZCIRLZ-UHFFFAOYSA-N 0.000 description 2
- 210000002569 neuron Anatomy 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000000180 1,2-diols Chemical class 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- OSEQIDSFSBWXRE-UHFFFAOYSA-N 3,4-dimethoxybenzonitrile Chemical compound COC1=CC=C(C#N)C=C1OC OSEQIDSFSBWXRE-UHFFFAOYSA-N 0.000 description 1
- NVTHWSJNXVDIKR-UHFFFAOYSA-N 3,5-dimethoxybenzonitrile Chemical compound COC1=CC(OC)=CC(C#N)=C1 NVTHWSJNXVDIKR-UHFFFAOYSA-N 0.000 description 1
- WPXCVBULBNOMKR-UHFFFAOYSA-N 3-(2-chlorophenyl)-n,5-dimethyl-1,2-oxazole-4-carboxamide Chemical compound CNC(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl WPXCVBULBNOMKR-UHFFFAOYSA-N 0.000 description 1
- KLXSUMLEPNAZFK-UHFFFAOYSA-N 3-methoxybenzonitrile Chemical compound COC1=CC=CC(C#N)=C1 KLXSUMLEPNAZFK-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- IKPLPVQRIVGAAA-UHFFFAOYSA-N 3-methyl-5-phenyl-1,2-oxazole-4-carboxamide Chemical compound CC1=NOC(C=2C=CC=CC=2)=C1C(N)=O IKPLPVQRIVGAAA-UHFFFAOYSA-N 0.000 description 1
- GLNQCTGGLIXRRJ-UHFFFAOYSA-N 3-methyl-5-phenyl-1,2-oxazole-4-carboxylic acid Chemical compound CC1=NOC(C=2C=CC=CC=2)=C1C(O)=O GLNQCTGGLIXRRJ-UHFFFAOYSA-N 0.000 description 1
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- IVSYNRMJMLDSIB-UHFFFAOYSA-N 4-[(4-methylpiperazin-1-yl)methyl]benzonitrile Chemical compound C1CN(C)CCN1CC1=CC=C(C#N)C=C1 IVSYNRMJMLDSIB-UHFFFAOYSA-N 0.000 description 1
- QCSOEUMGZOKXPJ-UHFFFAOYSA-N 4-[(dimethylamino)methyl]benzonitrile Chemical compound CN(C)CC1=CC=C(C#N)C=C1 QCSOEUMGZOKXPJ-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
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- BPMBNLJJRKCCRT-UHFFFAOYSA-N 4-phenylbenzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CC=CC=C1 BPMBNLJJRKCCRT-UHFFFAOYSA-N 0.000 description 1
- BTYZVJMWTDCGTR-UHFFFAOYSA-N 5,6-dimethyl-3-phenyl-[1,2]oxazolo[4,5-c]pyridin-4-one Chemical compound C1=2C(=O)N(C)C(C)=CC=2ON=C1C1=CC=CC=C1 BTYZVJMWTDCGTR-UHFFFAOYSA-N 0.000 description 1
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- CFEABDMXHARUJU-UHFFFAOYSA-N 5-methyl-3-phenyl-1,2-oxazole-4-carboxamide Chemical compound NC(=O)C1=C(C)ON=C1C1=CC=CC=C1 CFEABDMXHARUJU-UHFFFAOYSA-N 0.000 description 1
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- LJFFXXBCMTXSHN-UHFFFAOYSA-N 5-methyl-3-phenyl-6-pyridin-4-yl-[1,2]oxazolo[4,5-c]pyridin-4-one Chemical compound C1=2C(=O)N(C)C(C=3C=CN=CC=3)=CC=2ON=C1C1=CC=CC=C1 LJFFXXBCMTXSHN-UHFFFAOYSA-N 0.000 description 1
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- DPSRMQARUGRPPL-UHFFFAOYSA-N 5-methyl-6-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-3-phenyl-[1,2]oxazolo[4,3-c]pyridin-4-one Chemical compound C1CN(C)CCN1CC1=CC=C(C=2N(C(=O)C3=C(C=4C=CC=CC=4)ON=C3C=2)C)C=C1 DPSRMQARUGRPPL-UHFFFAOYSA-N 0.000 description 1
- RIBDJXAYIQCEGU-UHFFFAOYSA-N 6-(2,4-dimethoxyphenyl)-5-methyl-3-phenyl-[1,2]oxazolo[4,5-c]pyridin-4-one Chemical compound COC1=CC(OC)=CC=C1C(N(C1=O)C)=CC2=C1C(C=1C=CC=CC=1)=NO2 RIBDJXAYIQCEGU-UHFFFAOYSA-N 0.000 description 1
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- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
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- 239000012190 activator Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
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- 238000004458 analytical method Methods 0.000 description 1
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- 239000008346 aqueous phase Substances 0.000 description 1
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- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
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- 230000004071 biological effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229960002802 bromocriptine Drugs 0.000 description 1
- OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
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- JRURYQJSLYLRLN-BJMVGYQFSA-N entacapone Chemical compound CCN(CC)C(=O)C(\C#N)=C\C1=CC(O)=C(O)C([N+]([O-])=O)=C1 JRURYQJSLYLRLN-BJMVGYQFSA-N 0.000 description 1
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- JTUQHTUQSMTHHC-UHFFFAOYSA-N methyl 4-(5-methyl-4-oxo-3-phenyl-[1,2]oxazolo[4,3-c]pyridin-6-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC2=NOC(C=3C=CC=CC=3)=C2C(=O)N1C JTUQHTUQSMTHHC-UHFFFAOYSA-N 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- HCUIEGLRDNPODU-UHFFFAOYSA-N n-cyclopropyl-5-methyl-3-phenyl-1,2-oxazole-4-carboxamide Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C(=O)NC1CC1 HCUIEGLRDNPODU-UHFFFAOYSA-N 0.000 description 1
- WUZODTCWKPXULS-UHFFFAOYSA-N n-ethyl-5-methyl-3-phenyl-1,2-oxazole-4-carboxamide Chemical compound CCNC(=O)C1=C(C)ON=C1C1=CC=CC=C1 WUZODTCWKPXULS-UHFFFAOYSA-N 0.000 description 1
- MFDUBANTKQQBFU-UHFFFAOYSA-N n-methoxy-4-(2-methoxyethoxymethyl)-n-methylbenzamide Chemical compound COCCOCC1=CC=C(C(=O)N(C)OC)C=C1 MFDUBANTKQQBFU-UHFFFAOYSA-N 0.000 description 1
- OJGUHMWGMBWFPG-UHFFFAOYSA-N n-methyl-1,2-oxazole-4-carboxamide Chemical compound CNC(=O)C=1C=NOC=1 OJGUHMWGMBWFPG-UHFFFAOYSA-N 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 108020004017 nuclear receptors Proteins 0.000 description 1
- 102000006255 nuclear receptors Human genes 0.000 description 1
- 108091008686 nuclear receptors type II Proteins 0.000 description 1
- 102000027507 nuclear receptors type II Human genes 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 1
- 230000023603 positive regulation of transcription initiation, DNA-dependent Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229960003089 pramipexole Drugs 0.000 description 1
- FASDKYOPVNHBLU-ZETCQYMHSA-N pramipexole Chemical compound C1[C@@H](NCCC)CCC2=C1SC(N)=N2 FASDKYOPVNHBLU-ZETCQYMHSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229960003946 selegiline Drugs 0.000 description 1
- MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical compound C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 229960004603 tolcapone Drugs 0.000 description 1
- MIQPIUSUKVNLNT-UHFFFAOYSA-N tolcapone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC(O)=C(O)C([N+]([O-])=O)=C1 MIQPIUSUKVNLNT-UHFFFAOYSA-N 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
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Classifications
-
- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0119911.6A GB0119911D0 (en) | 2001-08-15 | 2001-08-15 | Organic Compounds |
| GB0119911.6 | 2001-08-15 | ||
| PCT/EP2002/009134 WO2003015780A2 (en) | 2001-08-15 | 2002-08-14 | Isoxazolopyridinones and use thereof in the treatment of parkinson's disease |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20040029429A true KR20040029429A (ko) | 2004-04-06 |
Family
ID=9920454
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR10-2004-7002124A Ceased KR20040029429A (ko) | 2001-08-15 | 2002-08-14 | 이속사졸로피리디논 및 파킨슨병의 치료에 있어서 그의용도 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US7087756B2 (enExample) |
| EP (1) | EP1418912B1 (enExample) |
| JP (1) | JP2005501847A (enExample) |
| KR (1) | KR20040029429A (enExample) |
| CN (1) | CN100384418C (enExample) |
| AR (1) | AR036351A1 (enExample) |
| AT (1) | ATE355059T1 (enExample) |
| BR (1) | BR0211903A (enExample) |
| CA (1) | CA2454762A1 (enExample) |
| CO (1) | CO5560566A2 (enExample) |
| DE (1) | DE60218484T2 (enExample) |
| EC (1) | ECSP044971A (enExample) |
| ES (1) | ES2282467T3 (enExample) |
| GB (1) | GB0119911D0 (enExample) |
| HU (1) | HUP0401325A3 (enExample) |
| IL (1) | IL160018A0 (enExample) |
| MX (1) | MXPA04001419A (enExample) |
| NO (1) | NO20040659D0 (enExample) |
| PE (1) | PE20030356A1 (enExample) |
| PL (1) | PL366848A1 (enExample) |
| PT (1) | PT1418912E (enExample) |
| RU (1) | RU2004107847A (enExample) |
| WO (1) | WO2003015780A2 (enExample) |
| ZA (1) | ZA200400525B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20170033630A (ko) | 2015-09-17 | 2017-03-27 | (주)다올 | 도로용 경계블럭 |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2451057A1 (en) * | 2001-06-14 | 2002-12-27 | Banyu Pharmaceutical Co., Ltd. | Novel isoxazolopyridone derivatives and use thereof |
| US7820705B2 (en) * | 2004-05-14 | 2010-10-26 | Irm Llc | Compounds and compositions as PPAR modulators |
| CA2642672A1 (en) * | 2006-02-16 | 2007-08-30 | The Mclean Hospital Corporation | Methods and compositions for the treatment of parkinson's disease |
| AU2007275301A1 (en) | 2006-07-20 | 2008-01-24 | Amgen Inc. | Substituted azole aromatic heterocycles as inhibitors of 11-beta-HSD-1 |
| FR2906250B1 (fr) * | 2006-09-22 | 2008-10-31 | Sanofi Aventis Sa | Derives de 2-aryl-6phenyl-imidazo(1,2-a) pyridines, leur preparation et leur application en therapeutique |
| FR2933609B1 (fr) | 2008-07-10 | 2010-08-27 | Fournier Lab Sa | Utilisation de derives d'indole comme activateurs de nurr-1, pour le traitement de la maladie de parkinson. |
| EP2376079B1 (en) * | 2009-01-13 | 2016-08-10 | Van Andel Research Institute | Methods of using substituted isoxazolo pyridinones as dissociated glucocorticoids |
| FR2950053B1 (fr) | 2009-09-11 | 2014-08-01 | Fournier Lab Sa | Utilisation de derives d'indole benzoique comme activateurs de nurr-1, pour le traitement de la maladie de parkinson |
| FR2955110A1 (fr) | 2010-01-08 | 2011-07-15 | Fournier Lab Sa | Nouveaux derives de type pyrrolopyridine benzoique |
| DE102011085038A1 (de) | 2011-10-21 | 2013-04-25 | Tesa Se | Verfahren zur Kapselung einer elektronischen Anordnung |
| WO2015048316A1 (en) | 2013-09-25 | 2015-04-02 | Van Andel Research Institute | Highly potent glucocorticoids |
| JP7146750B2 (ja) | 2016-10-14 | 2022-10-04 | ヴァン アンデル リサーチ インスティテュート | 非常に強力な糖質コルチコイドの構造およびデザインのための機構 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7602542L (sv) | 1975-03-14 | 1976-09-15 | Sandoz Ag | 3-(alfa-iminobensyl)-4-hydroxi-2(lh)-pyridoner |
| US4064251A (en) * | 1976-06-25 | 1977-12-20 | Sandoz, Inc. | Substituted hydroxy pyridones |
| US4049813A (en) * | 1976-07-15 | 1977-09-20 | Sandoz, Inc. | Substituted isoxazolo pyridinones |
| DE2801190A1 (de) * | 1977-01-19 | 1978-07-20 | Sandoz Ag | 3-(alpha-iminobenzyl)-4-hydroxy-2(1h)- pyridon-derivat |
| US4238616A (en) * | 1977-01-19 | 1980-12-09 | Sandoz, Inc. | 3-(Substituted)phenyl-5-(β-hydroxyphenethyl)-N-(alkyl)-isoxazole-4-carboxamides |
| US4113727A (en) * | 1977-04-26 | 1978-09-12 | Sandoz, Inc. | Process for the preparation of substituted isoxazolo[4,5-c]pyridin-4-(5H)-ones |
| CA2451057A1 (en) * | 2001-06-14 | 2002-12-27 | Banyu Pharmaceutical Co., Ltd. | Novel isoxazolopyridone derivatives and use thereof |
-
2001
- 2001-08-15 GB GBGB0119911.6A patent/GB0119911D0/en not_active Ceased
-
2002
- 2002-08-13 AR ARP020103046A patent/AR036351A1/es unknown
- 2002-08-14 HU HU0401325A patent/HUP0401325A3/hu unknown
- 2002-08-14 US US10/486,569 patent/US7087756B2/en not_active Expired - Fee Related
- 2002-08-14 PL PL02366848A patent/PL366848A1/xx not_active Application Discontinuation
- 2002-08-14 PT PT02772157T patent/PT1418912E/pt unknown
- 2002-08-14 JP JP2003520739A patent/JP2005501847A/ja not_active Withdrawn
- 2002-08-14 WO PCT/EP2002/009134 patent/WO2003015780A2/en not_active Ceased
- 2002-08-14 BR BR0211903-0A patent/BR0211903A/pt not_active IP Right Cessation
- 2002-08-14 DE DE60218484T patent/DE60218484T2/de not_active Expired - Lifetime
- 2002-08-14 CN CNB028159268A patent/CN100384418C/zh not_active Expired - Fee Related
- 2002-08-14 MX MXPA04001419A patent/MXPA04001419A/es unknown
- 2002-08-14 CA CA002454762A patent/CA2454762A1/en not_active Abandoned
- 2002-08-14 AT AT02772157T patent/ATE355059T1/de not_active IP Right Cessation
- 2002-08-14 IL IL16001802A patent/IL160018A0/xx unknown
- 2002-08-14 EP EP02772157A patent/EP1418912B1/en not_active Expired - Lifetime
- 2002-08-14 PE PE2002000734A patent/PE20030356A1/es not_active Application Discontinuation
- 2002-08-14 KR KR10-2004-7002124A patent/KR20040029429A/ko not_active Ceased
- 2002-08-14 RU RU2004107847/15A patent/RU2004107847A/ru not_active Application Discontinuation
- 2002-08-14 ES ES02772157T patent/ES2282467T3/es not_active Expired - Lifetime
-
2004
- 2004-01-23 ZA ZA200400525A patent/ZA200400525B/en unknown
- 2004-02-03 EC EC2004004971A patent/ECSP044971A/es unknown
- 2004-02-13 NO NO20040659A patent/NO20040659D0/no not_active Application Discontinuation
- 2004-03-12 CO CO04023011A patent/CO5560566A2/es not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20170033630A (ko) | 2015-09-17 | 2017-03-27 | (주)다올 | 도로용 경계블럭 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005501847A (ja) | 2005-01-20 |
| CO5560566A2 (es) | 2005-09-30 |
| DE60218484D1 (de) | 2007-04-12 |
| WO2003015780A3 (en) | 2003-11-13 |
| HUP0401325A2 (hu) | 2004-10-28 |
| WO2003015780A2 (en) | 2003-02-27 |
| MXPA04001419A (es) | 2004-05-27 |
| PL366848A1 (en) | 2005-02-07 |
| ZA200400525B (en) | 2005-04-01 |
| CN1635889A (zh) | 2005-07-06 |
| ATE355059T1 (de) | 2006-03-15 |
| DE60218484T2 (de) | 2007-11-15 |
| ES2282467T3 (es) | 2007-10-16 |
| US7087756B2 (en) | 2006-08-08 |
| ECSP044971A (es) | 2004-03-23 |
| GB0119911D0 (en) | 2001-10-10 |
| NO20040659L (no) | 2004-02-13 |
| RU2004107847A (ru) | 2005-05-10 |
| CN100384418C (zh) | 2008-04-30 |
| BR0211903A (pt) | 2004-09-21 |
| CA2454762A1 (en) | 2003-02-27 |
| AR036351A1 (es) | 2004-09-01 |
| IL160018A0 (en) | 2004-06-20 |
| US20040248893A1 (en) | 2004-12-09 |
| PE20030356A1 (es) | 2003-05-14 |
| PT1418912E (pt) | 2007-05-31 |
| EP1418912A2 (en) | 2004-05-19 |
| EP1418912B1 (en) | 2007-02-28 |
| NO20040659D0 (no) | 2004-02-13 |
| HUP0401325A3 (en) | 2005-09-28 |
| WO2003015780A8 (en) | 2004-05-21 |
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