DE60218484T2 - Isoxazolopyridinone - Google Patents
Isoxazolopyridinone Download PDFInfo
- Publication number
- DE60218484T2 DE60218484T2 DE60218484T DE60218484T DE60218484T2 DE 60218484 T2 DE60218484 T2 DE 60218484T2 DE 60218484 T DE60218484 T DE 60218484T DE 60218484 T DE60218484 T DE 60218484T DE 60218484 T2 DE60218484 T2 DE 60218484T2
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- pyridin
- isoxazolo
- methyl
- ylmethyl
- 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
Links
- XDWKYQRZDNGJNB-UHFFFAOYSA-N chembl246652 Chemical compound C1=2C(=O)NC(C=3C=CC=CC=3)=CC=2ON=C1C1=CC=CC=C1 XDWKYQRZDNGJNB-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 51
- 150000003839 salts Chemical group 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 13
- -1 4-diethylaminophenyl Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- 239000012458 free base Substances 0.000 claims description 9
- CABBIZSFTLIHJT-UHFFFAOYSA-N 5-methyl-3,6-diphenyl-[1,2]oxazolo[4,3-c]pyridin-4-one Chemical compound C=12C(=O)N(C)C(C=3C=CC=CC=3)=CC2=NOC=1C1=CC=CC=C1 CABBIZSFTLIHJT-UHFFFAOYSA-N 0.000 claims description 5
- DGAIEYJJQNSIGM-UHFFFAOYSA-N 5-methyl-6-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-3-phenyl-[1,2]oxazolo[4,5-c]pyridin-4-one Chemical group C1CN(C)CCN1CC1=CC=C(C=2N(C(=O)C=3C(C=4C=CC=CC=4)=NOC=3C=2)C)C=C1 DGAIEYJJQNSIGM-UHFFFAOYSA-N 0.000 claims description 5
- IBQKWQHKJWZQRA-UHFFFAOYSA-N 5-methyl-3-phenyl-6-[4-(pyrrol-1-ylmethyl)phenyl]-[1,2]oxazolo[4,5-c]pyridin-4-one Chemical compound C1=2C(=O)N(C)C(C=3C=CC(CN4C=CC=C4)=CC=3)=CC=2ON=C1C1=CC=CC=C1 IBQKWQHKJWZQRA-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 229940079593 drug Drugs 0.000 claims description 4
- UELJMYRIGJUYLR-UHFFFAOYSA-N 3,6-diphenyl-5-propyl-[1,2]oxazolo[4,5-c]pyridin-4-one Chemical compound C1=2C(=O)N(CCC)C(C=3C=CC=CC=3)=CC=2ON=C1C1=CC=CC=C1 UELJMYRIGJUYLR-UHFFFAOYSA-N 0.000 claims description 3
- ZBRIOJKIBZMZIZ-UHFFFAOYSA-N 5-cyclopropyl-3,6-diphenyl-[1,2]oxazolo[4,5-c]pyridin-4-one Chemical compound C=1C=CC=CC=1C1=CC=2ON=C(C=3C=CC=CC=3)C=2C(=O)N1C1CC1 ZBRIOJKIBZMZIZ-UHFFFAOYSA-N 0.000 claims description 3
- QKGMJCLWMCCRRB-UHFFFAOYSA-N 5-methyl-3-phenyl-6-[4-(phenylmethoxymethyl)phenyl]-[1,2]oxazolo[4,5-c]pyridin-4-one Chemical compound C1=2C(=O)N(C)C(C=3C=CC(COCC=4C=CC=CC=4)=CC=3)=CC=2ON=C1C1=CC=CC=C1 QKGMJCLWMCCRRB-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- LUTLTCWBCIRAHM-UHFFFAOYSA-N 6-(1,3-benzodioxol-5-yl)-3-(2-chlorophenyl)-5-methyl-[1,2]oxazolo[4,5-c]pyridin-4-one Chemical compound C1=2C(=O)N(C)C(C=3C=C4OCOC4=CC=3)=CC=2ON=C1C1=CC=CC=C1Cl LUTLTCWBCIRAHM-UHFFFAOYSA-N 0.000 claims description 3
- OPIIMVDOIZEYOE-UHFFFAOYSA-N 6-(1,3-benzodioxol-5-yl)-5-cyclopropyl-3-phenyl-[1,2]oxazolo[4,5-c]pyridin-4-one Chemical compound C=1C=C2OCOC2=CC=1C1=CC=2ON=C(C=3C=CC=CC=3)C=2C(=O)N1C1CC1 OPIIMVDOIZEYOE-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- KCZHOYHCNBXGMF-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-methyl-3-phenyl-[1,2]oxazolo[4,3-c]pyridin-4-one Chemical compound C=12C(=O)N(C)C(C=3C=CC(Cl)=CC=3)=CC2=NOC=1C1=CC=CC=C1 KCZHOYHCNBXGMF-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- GZVFWTYXCJWBFS-UHFFFAOYSA-N 6-[4-(methoxymethyl)phenyl]-5-methyl-3-phenyl-[1,2]oxazolo[4,5-c]pyridin-4-one Chemical compound C1=CC(COC)=CC=C1C(N(C1=O)C)=CC2=C1C(C=1C=CC=CC=1)=NO2 GZVFWTYXCJWBFS-UHFFFAOYSA-N 0.000 claims description 3
- LCCITJNWBGGGIJ-UHFFFAOYSA-N 6-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-3-phenyl-5H-[1,2]oxazolo[4,3-c]pyridin-4-one Chemical compound C1CN(C)CCN1CC1=CC=C(C=2NC(=O)C3=C(C=4C=CC=CC=4)ON=C3C=2)C=C1 LCCITJNWBGGGIJ-UHFFFAOYSA-N 0.000 claims description 3
- QIPODYCQCKHDDA-UHFFFAOYSA-N 6-[4-[(dimethylamino)methyl]phenyl]-3-phenyl-5H-[1,2]oxazolo[4,3-c]pyridin-4-one Chemical compound C1=CC(CN(C)C)=CC=C1C1=CC2=NOC(C=3C=CC=CC=3)=C2C(=O)N1 QIPODYCQCKHDDA-UHFFFAOYSA-N 0.000 claims description 3
- KNKXNQCKNMNFCU-UHFFFAOYSA-N 6-cyclohexyl-5-ethyl-3-phenyl-[1,2]oxazolo[4,5-c]pyridin-4-one Chemical compound C1=2C(=O)N(CC)C(C3CCCCC3)=CC=2ON=C1C1=CC=CC=C1 KNKXNQCKNMNFCU-UHFFFAOYSA-N 0.000 claims description 3
- FMSSTTMLKQLLII-UHFFFAOYSA-N 6-cyclohexyl-5-methyl-3-phenyl-[1,2]oxazolo[4,5-c]pyridin-4-one Chemical compound C1=2C(=O)N(C)C(C3CCCCC3)=CC=2ON=C1C1=CC=CC=C1 FMSSTTMLKQLLII-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 229940088679 drug related substance Drugs 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- 239000008024 pharmaceutical diluent Substances 0.000 claims 1
- 238000001819 mass spectrum Methods 0.000 description 34
- 239000007787 solid Substances 0.000 description 29
- 239000000243 solution Substances 0.000 description 25
- 239000003795 chemical substances by application Substances 0.000 description 23
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 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
- 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
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 150000002825 nitriles Chemical class 0.000 description 8
- 208000018737 Parkinson disease Diseases 0.000 description 7
- 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
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- 238000006243 chemical reaction Methods 0.000 description 5
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 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 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
- 241001465754 Metazoa Species 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
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 4
- 229960003638 dopamine Drugs 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
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- 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 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
- URQHVJOTYUGJLC-UHFFFAOYSA-N 1,2-oxazole 1H-pyridin-2-one Chemical class N1C(C=CC=C1)=O.O1N=CC=C1 URQHVJOTYUGJLC-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- YCAACZFPADQMAR-UHFFFAOYSA-N 6-[4-(2-methoxyethoxymethyl)phenyl]-5-methyl-3-phenyl-[1,2]oxazolo[4,5-c]pyridin-4-one Chemical compound C1=CC(COCCOC)=CC=C1C(N(C1=O)C)=CC2=C1C(C=1C=CC=CC=1)=NO2 YCAACZFPADQMAR-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
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- 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 3
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- QCSOEUMGZOKXPJ-UHFFFAOYSA-N 4-[(dimethylamino)methyl]benzonitrile Chemical compound CN(C)CC1=CC=C(C#N)C=C1 QCSOEUMGZOKXPJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
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- KGFOGVACSJUUCO-UHFFFAOYSA-N 5-methyl-3-phenyl-6-[4-(tetrazol-1-ylmethyl)phenyl]-[1,2]oxazolo[4,5-c]pyridin-4-one Chemical compound C1=2C(=O)N(C)C(C=3C=CC(CN4N=NN=C4)=CC=3)=CC=2ON=C1C1=CC=CC=C1 KGFOGVACSJUUCO-UHFFFAOYSA-N 0.000 description 2
- KQVFNVQDUTYNCI-UHFFFAOYSA-N 5-methyl-6-(4-phenoxyphenyl)-3-phenyl-[1,2]oxazolo[4,5-c]pyridin-4-one Chemical compound C1=2C(=O)N(C)C(C=3C=CC(OC=4C=CC=CC=4)=CC=3)=CC=2ON=C1C1=CC=CC=C1 KQVFNVQDUTYNCI-UHFFFAOYSA-N 0.000 description 2
- ULIDMONIXZNCET-UHFFFAOYSA-N 6-(1,3-benzodioxol-5-yl)-5-ethyl-3-phenyl-[1,2]oxazolo[4,5-c]pyridin-4-one Chemical compound C1=2C(=O)N(CC)C(C=3C=C4OCOC4=CC=3)=CC=2ON=C1C1=CC=CC=C1 ULIDMONIXZNCET-UHFFFAOYSA-N 0.000 description 2
- BBPFMYPJIKCJKZ-UHFFFAOYSA-N 6-(3,4-dimethoxyphenyl)-5-methyl-3-phenyl-[1,2]oxazolo[4,5-c]pyridin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C(N(C1=O)C)=CC2=C1C(C=1C=CC=CC=1)=NO2 BBPFMYPJIKCJKZ-UHFFFAOYSA-N 0.000 description 2
- JAERTDMSEBWFIF-UHFFFAOYSA-N 6-(3,5-dimethoxyphenyl)-5-methyl-3-phenyl-[1,2]oxazolo[4,5-c]pyridin-4-one Chemical compound COC1=CC(OC)=CC(C=2N(C(=O)C=3C(C=4C=CC=CC=4)=NOC=3C=2)C)=C1 JAERTDMSEBWFIF-UHFFFAOYSA-N 0.000 description 2
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- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 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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- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
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- 239000003446 ligand Substances 0.000 description 1
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- 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
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- FASDKYOPVNHBLU-ZETCQYMHSA-N pramipexole Chemical compound C1[C@@H](NCCC)CCC2=C1SC(N)=N2 FASDKYOPVNHBLU-ZETCQYMHSA-N 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 | 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 (2)
| Publication Number | Publication Date |
|---|---|
| DE60218484D1 DE60218484D1 (de) | 2007-04-12 |
| DE60218484T2 true DE60218484T2 (de) | 2007-11-15 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60218484T Expired - Lifetime DE60218484T2 (de) | 2001-08-15 | 2002-08-14 | Isoxazolopyridinone |
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) |
Families Citing this family (13)
| 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 |
| KR20170033630A (ko) | 2015-09-17 | 2017-03-27 | (주)다올 | 도로용 경계블럭 |
| 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
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 |
| 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 |
| KR20040029429A (ko) | 2004-04-06 |
| WO2003015780A8 (en) | 2004-05-21 |
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