JP2005526814A5 - - Google Patents
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- Publication number
- JP2005526814A5 JP2005526814A5 JP2003580319A JP2003580319A JP2005526814A5 JP 2005526814 A5 JP2005526814 A5 JP 2005526814A5 JP 2003580319 A JP2003580319 A JP 2003580319A JP 2003580319 A JP2003580319 A JP 2003580319A JP 2005526814 A5 JP2005526814 A5 JP 2005526814A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- alkyl
- compound
- hydroxy
- indol
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 42
- 125000000217 alkyl group Chemical group 0.000 claims 38
- 125000005842 heteroatoms Chemical group 0.000 claims 21
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 19
- -1 (CO) OR 4 Chemical group 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
- 125000002877 alkyl aryl group Chemical group 0.000 claims 11
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 10
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 239000012458 free base Substances 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 239000011780 sodium chloride Substances 0.000 claims 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 7
- 206010057668 Cognitive disease Diseases 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 5
- 239000002904 solvent Substances 0.000 claims 5
- 206010012289 Dementia Diseases 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 3
- 201000011240 frontotemporal dementia Diseases 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- 206010001897 Alzheimer's disease Diseases 0.000 claims 2
- 206010004938 Bipolar disease Diseases 0.000 claims 2
- LCJSFFYXNSCWRH-UHFFFAOYSA-N Cl.OC=1NC2=CC=C([N+]([O-])=O)C=C2C=1C(N=C1)=CC=C1CN1CCOCC1 Chemical compound Cl.OC=1NC2=CC=C([N+]([O-])=O)C=C2C=1C(N=C1)=CC=C1CN1CCOCC1 LCJSFFYXNSCWRH-UHFFFAOYSA-N 0.000 claims 2
- XBLVHTDFJBKJLG-UHFFFAOYSA-N Ethyl nicotinate Chemical group CCOC(=O)C1=CC=CN=C1 XBLVHTDFJBKJLG-UHFFFAOYSA-N 0.000 claims 2
- 102000001267 GSK3 Human genes 0.000 claims 2
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims 2
- 206010027175 Memory impairment Diseases 0.000 claims 2
- APRYBBRXBYNGRD-WLHGVMLRSA-N OC(=O)\C=C\C(O)=O.C1CN(C)CCN1S(=O)(=O)c1ccc(-c2c([nH]c3ccc(cc32)-c2cscn2)O)nc1 Chemical compound OC(=O)\C=C\C(O)=O.C1CN(C)CCN1S(=O)(=O)c1ccc(-c2c([nH]c3ccc(cc32)-c2cscn2)O)nc1 APRYBBRXBYNGRD-WLHGVMLRSA-N 0.000 claims 2
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- BXPZRULXWMCKOH-UHFFFAOYSA-N 2-oxo-3-[5-(4-propan-2-ylpiperazin-1-yl)sulfonyl-1H-pyridin-2-ylidene]-1H-indole-5-carbonitrile;hydrochloride Chemical compound Cl.C1CN(C(C)C)CCN1S(=O)(=O)C(C=C1)=CNC1=C1C2=CC(C#N)=CC=C2NC1=O BXPZRULXWMCKOH-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N 289-95-2 Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- BJHCVWGYSOABCU-UHFFFAOYSA-N 3-(5-morpholin-4-ylsulfonyl-1H-pyridin-2-ylidene)-2-oxo-1H-indole-5-carbonitrile Chemical compound O=C1NC2=CC=C(C#N)C=C2C1=C(C=C1)NC=C1S(=O)(=O)N1CCOCC1 BJHCVWGYSOABCU-UHFFFAOYSA-N 0.000 claims 1
- KYLRDRKFCIOGBQ-UHFFFAOYSA-N 3-[4-(2-morpholin-4-ylethoxy)-1H-pyrimidin-6-ylidene]-2-oxo-1H-indole-5-carbonitrile Chemical compound O=C1NC2=CC=C(C#N)C=C2C1=C(C=1)NC=NC=1OCCN1CCOCC1 KYLRDRKFCIOGBQ-UHFFFAOYSA-N 0.000 claims 1
- PAFGLOMRDMBEAX-UHFFFAOYSA-N 3-[4-(4-methylpiperazine-1-carbonyl)-1H-pyridin-2-ylidene]-2-oxo-1H-indole-5-carbonitrile;hydrochloride Chemical compound Cl.C1CN(C)CCN1C(=O)C(C=CN1)=CC1=C1C2=CC(C#N)=CC=C2NC1=O PAFGLOMRDMBEAX-UHFFFAOYSA-N 0.000 claims 1
- BCEOYEBYWFHSTK-UHFFFAOYSA-N 3-[5-(4-benzylpiperazin-1-yl)sulfonyl-1H-pyridin-2-ylidene]-2-oxo-1H-indole-5-carbonitrile;hydrochloride Chemical compound Cl.O=C1NC2=CC=C(C#N)C=C2C1=C(C=C1)NC=C1S(=O)(=O)N(CC1)CCN1CC1=CC=CC=C1 BCEOYEBYWFHSTK-UHFFFAOYSA-N 0.000 claims 1
- AMSYBYIIJDKPBK-UHFFFAOYSA-N 3-[5-(4-ethylpiperazin-1-yl)sulfonyl-1H-pyridin-2-ylidene]-2-oxo-1H-indole-5-carbonitrile;hydrochloride Chemical compound Cl.C1CN(CC)CCN1S(=O)(=O)C(C=C1)=CNC1=C1C2=CC(C#N)=CC=C2NC1=O AMSYBYIIJDKPBK-UHFFFAOYSA-N 0.000 claims 1
- UMXLNSZEKDCXCB-UHFFFAOYSA-N 3-[5-(4-methylpiperazin-1-yl)sulfonyl-1H-pyridin-2-ylidene]-1H-indol-2-one;hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C(C=C1)=CNC1=C1C2=CC=CC=C2NC1=O UMXLNSZEKDCXCB-UHFFFAOYSA-N 0.000 claims 1
- WVEZDRAIFCOSQV-UHFFFAOYSA-N 3-[5-(4-methylpiperazin-1-yl)sulfonyl-1H-pyridin-2-ylidene]-2-oxo-1H-indole-6-carbonitrile;hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C(C=C1)=CNC1=C1C2=CC=C(C#N)C=C2NC1=O WVEZDRAIFCOSQV-UHFFFAOYSA-N 0.000 claims 1
- FETFLDXUBOHSSU-UHFFFAOYSA-N 3-[5-(4-methylpiperazine-1-carbonyl)-1H-pyridin-2-ylidene]-2-oxo-1H-indole-5-carbonitrile Chemical compound C1CN(C)CCN1C(=O)C(C=C1)=CNC1=C1C2=CC(C#N)=CC=C2NC1=O FETFLDXUBOHSSU-UHFFFAOYSA-N 0.000 claims 1
- JULOXTBHCHEFBE-UHFFFAOYSA-N 3-[5-(morpholin-4-ylmethyl)-1H-pyridin-2-ylidene]-2-oxo-1H-indole-5-carbonitrile Chemical compound O=C1NC2=CC=C(C#N)C=C2C1=C(C=C1)NC=C1CN1CCOCC1 JULOXTBHCHEFBE-UHFFFAOYSA-N 0.000 claims 1
- HZAKUEISNQJSPN-UHFFFAOYSA-N 3-[5-(morpholin-4-ylmethyl)-1H-pyridin-2-ylidene]-2-oxo-1H-indole-5-carbonitrile;hydrochloride Chemical compound Cl.O=C1NC2=CC=C(C#N)C=C2C1=C(C=C1)NC=C1CN1CCOCC1 HZAKUEISNQJSPN-UHFFFAOYSA-N 0.000 claims 1
- VYGGYKVGOUVRDI-UHFFFAOYSA-N 3-[5-(morpholin-4-ylmethyl)-1H-pyridin-2-ylidene]-5-pyridin-3-yl-1H-indol-2-one Chemical group O=C1NC2=CC=C(C=3C=NC=CC=3)C=C2C1=C(C=C1)NC=C1CN1CCOCC1 VYGGYKVGOUVRDI-UHFFFAOYSA-N 0.000 claims 1
- HLADNXKLUQEVGK-UHFFFAOYSA-N 3-[5-(morpholin-4-ylmethyl)-1H-pyridin-2-ylidene]-5-thiophen-2-yl-1H-indol-2-one;hydrochloride Chemical compound Cl.O=C1NC2=CC=C(C=3SC=CC=3)C=C2C1=C(C=C1)NC=C1CN1CCOCC1 HLADNXKLUQEVGK-UHFFFAOYSA-N 0.000 claims 1
- BDFFKZNPNYSTSM-UHFFFAOYSA-N 3-[5-(morpholine-4-carbonyl)-1H-pyridin-2-ylidene]-5-nitro-1H-indol-2-one Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)C1=C(C=C1)NC=C1C(=O)N1CCOCC1 BDFFKZNPNYSTSM-UHFFFAOYSA-N 0.000 claims 1
- WGYAVLPLFAIQFZ-UHFFFAOYSA-N 3-[5-[(4-methylpiperidin-1-yl)methyl]-1H-pyridin-2-ylidene]-2-oxo-1H-indole-5-carbonitrile Chemical compound C1CC(C)CCN1CC(C=C1)=CNC1=C1C2=CC(C#N)=CC=C2NC1=O WGYAVLPLFAIQFZ-UHFFFAOYSA-N 0.000 claims 1
- JFADNTRJVAWGBM-UHFFFAOYSA-N 3-[5-[4-(3-methylbutyl)piperazin-1-yl]sulfonyl-1H-pyridin-2-ylidene]-2-oxo-1H-indole-5-carbonitrile;hydrochloride Chemical compound Cl.C1CN(CCC(C)C)CCN1S(=O)(=O)C(C=C1)=CNC1=C1C2=CC(C#N)=CC=C2NC1=O JFADNTRJVAWGBM-UHFFFAOYSA-N 0.000 claims 1
- DGYOQSAUPDVPQH-UHFFFAOYSA-N 3-fluoro-3-[5-(morpholin-4-ylmethyl)pyridin-2-yl]-2-oxo-1H-indole-6-carbonitrile;hydrochloride Chemical compound Cl.O=C1NC2=CC(C#N)=CC=C2C1(F)C(N=C1)=CC=C1CN1CCOCC1 DGYOQSAUPDVPQH-UHFFFAOYSA-N 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- OOWYIZHCMMOPNS-UHFFFAOYSA-N 6-(5-cyano-2-oxo-1H-indol-3-ylidene)-N-[2-(dimethylamino)ethyl]-N-methyl-1H-pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C1=CC(C(=O)N(C)CCN(C)C)=CNC1=C1C2=CC(C#N)=CC=C2NC1=O OOWYIZHCMMOPNS-UHFFFAOYSA-N 0.000 claims 1
- HAZWQEZMRAFTJF-UHFFFAOYSA-N 6-(5-cyano-2-oxo-1H-indol-3-ylidene)-N-methyl-N-(2-pyrrolidin-1-ylethyl)-1H-pyridine-3-sulfonamide;hydrochloride Chemical compound Cl.C=1NC(=C2C3=CC(=CC=C3NC2=O)C#N)C=CC=1S(=O)(=O)N(C)CCN1CCCC1 HAZWQEZMRAFTJF-UHFFFAOYSA-N 0.000 claims 1
- 206010065040 AIDS dementia complex Diseases 0.000 claims 1
- 208000000044 Amnesia Diseases 0.000 claims 1
- 206010001954 Amnestic disease Diseases 0.000 claims 1
- 206010002026 Amyotrophic lateral sclerosis Diseases 0.000 claims 1
- 206010068168 Androgenetic alopecia Diseases 0.000 claims 1
- 210000004227 Basal Ganglia Anatomy 0.000 claims 1
- NYLFEHCKPMZKQY-UHFFFAOYSA-N C1C(N(C)C)CCN1CC1=CC=C(C=2C3=CC(=CC=C3NC=2O)C#N)N=C1 Chemical compound C1C(N(C)C)CCN1CC1=CC=C(C=2C3=CC(=CC=C3NC=2O)C#N)N=C1 NYLFEHCKPMZKQY-UHFFFAOYSA-N 0.000 claims 1
- BUHJHFJDPDIPMP-UHFFFAOYSA-N Cl.C1C(N(C)C)CCN1C(=O)C1=CC=C(C=2C3=CC(=CC=C3NC=2O)[N+]([O-])=O)N=C1 Chemical compound Cl.C1C(N(C)C)CCN1C(=O)C1=CC=C(C=2C3=CC(=CC=C3NC=2O)[N+]([O-])=O)N=C1 BUHJHFJDPDIPMP-UHFFFAOYSA-N 0.000 claims 1
- VBOGGFCZFUJSMT-UHFFFAOYSA-N Cl.C1CN(C)CCCN1CC1=CC=C(C=2C3=CC(=CC=C3NC=2O)C#N)N=C1 Chemical compound Cl.C1CN(C)CCCN1CC1=CC=C(C=2C3=CC(=CC=C3NC=2O)C#N)N=C1 VBOGGFCZFUJSMT-UHFFFAOYSA-N 0.000 claims 1
- AICZIXZCGTTZLV-UHFFFAOYSA-N Cl.C1CN(C)CCN1CC1=CC=C(C=2C3=CC(=CC=C3NC=2O)C#N)N=C1 Chemical compound Cl.C1CN(C)CCN1CC1=CC=C(C=2C3=CC(=CC=C3NC=2O)C#N)N=C1 AICZIXZCGTTZLV-UHFFFAOYSA-N 0.000 claims 1
- CCRQRQITUSYUCY-UHFFFAOYSA-N Cl.C1CN(C)CCN1S(=O)(=O)C(C=C1Br)=CN=C1C1=C(O)NC2=CC=C([N+]([O-])=O)C=C12 Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C(C=C1Br)=CN=C1C1=C(O)NC2=CC=C([N+]([O-])=O)C=C12 CCRQRQITUSYUCY-UHFFFAOYSA-N 0.000 claims 1
- SYFQOGMYKZJTMV-UHFFFAOYSA-N Cl.C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC(=CC=C3NC=2O)C#N)N=C1 Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC(=CC=C3NC=2O)C#N)N=C1 SYFQOGMYKZJTMV-UHFFFAOYSA-N 0.000 claims 1
- FLRICODGIDQWDO-UHFFFAOYSA-N Cl.C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC(=CC=C3NC=2O)C=2N=C(C)SC=2)N=C1 Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC(=CC=C3NC=2O)C=2N=C(C)SC=2)N=C1 FLRICODGIDQWDO-UHFFFAOYSA-N 0.000 claims 1
- ANSNPHYKHZDIDV-UHFFFAOYSA-N Cl.C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC=C(Cl)C=C3NC=2O)N=C1 Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC=C(Cl)C=C3NC=2O)N=C1 ANSNPHYKHZDIDV-UHFFFAOYSA-N 0.000 claims 1
- QBMKVGAHJVUDMD-UHFFFAOYSA-N Cl.OC=1NC2=CC(Br)=C(Br)C=C2C=1C(N=C1)=CC=C1CN1CCOCC1 Chemical compound Cl.OC=1NC2=CC(Br)=C(Br)C=C2C=1C(N=C1)=CC=C1CN1CCOCC1 QBMKVGAHJVUDMD-UHFFFAOYSA-N 0.000 claims 1
- ISCKFWGPRHZHEU-UHFFFAOYSA-N Cl.OC=1NC2=CC(Br)=CC=C2C=1C(N=C1)=CC=C1CN1CCOCC1 Chemical compound Cl.OC=1NC2=CC(Br)=CC=C2C=1C(N=C1)=CC=C1CN1CCOCC1 ISCKFWGPRHZHEU-UHFFFAOYSA-N 0.000 claims 1
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- XYQALSFZTTXKKD-UHFFFAOYSA-N Cl.OC=1NC2=CC=C(C#N)C=C2C=1C(N=C1)=CC=C1CN(CC1)CCC1N1CCCC1 Chemical compound Cl.OC=1NC2=CC=C(C#N)C=C2C=1C(N=C1)=CC=C1CN(CC1)CCC1N1CCCC1 XYQALSFZTTXKKD-UHFFFAOYSA-N 0.000 claims 1
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- FAABSFPFSLKXNZ-UHFFFAOYSA-N Cl.OC=1NC2=CC=C(C=3OC=CC=3)C=C2C=1C(N=C1)=CC=C1CN1CCOCC1 Chemical compound Cl.OC=1NC2=CC=C(C=3OC=CC=3)C=C2C=1C(N=C1)=CC=C1CN1CCOCC1 FAABSFPFSLKXNZ-UHFFFAOYSA-N 0.000 claims 1
- PCEVLYRCZVWKNL-UHFFFAOYSA-N Cl.OC=1NC2=CC=C([N+]([O-])=O)C=C2C=1C(N=C1)=CC=C1C(=O)N(CC1)CCC1N1CCCC1 Chemical compound Cl.OC=1NC2=CC=C([N+]([O-])=O)C=C2C=1C(N=C1)=CC=C1C(=O)N(CC1)CCC1N1CCCC1 PCEVLYRCZVWKNL-UHFFFAOYSA-N 0.000 claims 1
- 208000008208 Craniocerebral Trauma Diseases 0.000 claims 1
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- 150000001204 N-oxides Chemical class 0.000 claims 1
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- 210000002682 Neurofibrillary Tangles Anatomy 0.000 claims 1
- 208000006660 Niemann-Pick Disease Diseases 0.000 claims 1
- QFJWLSYVRJXJKO-WLHGVMLRSA-N OC(=O)\C=C\C(O)=O.C1CN(C)CCCN1S(=O)(=O)c1ccc(-c2c([nH]c3ccc(cc32)C#N)O)nc1 Chemical compound OC(=O)\C=C\C(O)=O.C1CN(C)CCCN1S(=O)(=O)c1ccc(-c2c([nH]c3ccc(cc32)C#N)O)nc1 QFJWLSYVRJXJKO-WLHGVMLRSA-N 0.000 claims 1
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- KPMVLWSSNOTENQ-UHFFFAOYSA-N OC=1NC2=CC=C(C#N)C=C2C=1C(N=C1)=CC=C1CN(CC1)CCN1C1=CC=CC=C1 Chemical group OC=1NC2=CC=C(C#N)C=C2C=1C(N=C1)=CC=C1CN(CC1)CCN1C1=CC=CC=C1 KPMVLWSSNOTENQ-UHFFFAOYSA-N 0.000 claims 1
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- FJVACSNRHIUTDK-UHFFFAOYSA-N OC=1NC2=CC=C(C#N)C=C2C=1C(N=C1)=CC=C1CN1CCCCC1 Chemical compound OC=1NC2=CC=C(C#N)C=C2C=1C(N=C1)=CC=C1CN1CCCCC1 FJVACSNRHIUTDK-UHFFFAOYSA-N 0.000 claims 1
- 206010061536 Parkinson's disease Diseases 0.000 claims 1
- 206010034010 Parkinsonism Diseases 0.000 claims 1
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims 1
- 201000011585 Pick's disease Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 201000004384 alopecia Diseases 0.000 claims 1
- 231100000360 alopecia Toxicity 0.000 claims 1
- 201000002996 androgenic alopecia Diseases 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 230000001684 chronic Effects 0.000 claims 1
- 230000002254 contraceptive Effects 0.000 claims 1
- 239000003433 contraceptive agent Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229940079593 drugs Drugs 0.000 claims 1
- POLXDZPHHGUNLA-UHFFFAOYSA-N ethyl 6-(5-nitro-2-oxo-1H-indol-3-ylidene)-1H-pyridine-3-carboxylate Chemical compound C1=CC(C(=O)OCC)=CNC1=C1C2=CC([N+]([O-])=O)=CC=C2NC1=O POLXDZPHHGUNLA-UHFFFAOYSA-N 0.000 claims 1
- 229940064982 ethylnicotinate Drugs 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
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| PCT/SE2003/000508 WO2003082853A1 (en) | 2002-03-28 | 2003-03-28 | New compounds |
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| JP2007155810A Division JP2007224051A (ja) | 2002-03-28 | 2007-06-13 | 新規な化合物 |
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| SE0302546D0 (sv) * | 2003-09-24 | 2003-09-24 | Astrazeneca Ab | New compounds |
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| JP5980808B2 (ja) | 2010-12-21 | 2016-08-31 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | トリアジニル−置換オキシインドール類を製造する方法 |
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| EP3400286A1 (en) | 2016-01-08 | 2018-11-14 | Massachusetts Institute Of Technology | Production of differentiated enteroendocrine cells and insulin producing cells |
| US10201540B2 (en) | 2016-03-02 | 2019-02-12 | Frequency Therapeutics, Inc. | Solubilized compositions for controlled proliferation of stem cells / generating inner ear hair cells using GSK3 inhibitors: I |
| US10213511B2 (en) | 2016-03-02 | 2019-02-26 | Frequency Therapeutics, Inc. | Thermoreversible compositions for administration of therapeutic agents |
| US11260130B2 (en) | 2016-03-02 | 2022-03-01 | Frequency Therapeutics, Inc. | Solubilized compositions for controlled proliferation of stem cells / generating inner ear hair cells using a GSK3 inhibitor: IV |
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- 2002-03-28 SE SE0200979A patent/SE0200979D0/xx unknown
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- 2003-03-28 EP EP03745498A patent/EP1492785B9/en not_active Expired - Lifetime
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- 2003-03-28 RU RU2004125146/04A patent/RU2338742C2/ru not_active IP Right Cessation
- 2003-03-28 US US10/509,268 patent/US7399780B2/en not_active Expired - Lifetime
- 2003-03-28 WO PCT/SE2003/000508 patent/WO2003082853A1/en active Application Filing
- 2003-03-28 PT PT03745498T patent/PT1492785E/pt unknown
- 2003-03-28 EP EP08157461A patent/EP1961748A3/en not_active Withdrawn
- 2003-03-28 CN CNB038073897A patent/CN100519550C/zh not_active Expired - Fee Related
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- 2003-03-28 AU AU2003216026A patent/AU2003216026B2/en not_active Ceased
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- 2003-03-28 CN CNA2006101537141A patent/CN1923812A/zh active Pending
- 2003-03-28 AT AT03745498T patent/ATE416171T1/de active
- 2003-03-28 UA UA20040806742A patent/UA79447C2/uk unknown
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