http://rdf.ncbi.nlm.nih.gov/pubchem/patent/AR-038996-A1
Outgoing Links
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| filingDate | 2003-03-17-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 2005-02-02-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | AR-038996-A1 |
| titleOfInvention | COMPOUNDS WITH INHIBITING EFFECT ON THE GSK3, PHARMACEUTICAL FORMULATIONS CONTAINING THEM, AND THE SAME PREPARATION PROCESS |
| abstract | Compounds of formula (1) and (2), as well as a process for their preparation and intermediates used therein, pharmaceutical formulations comprising said therapeutically active compounds and the use of said active compounds in therapy. These compounds are suitable for inhibiting the glycogen synthase kinase-3 or GSK3 enzyme. This is highly expressed in the central and peripheral nervous system and in other tissues, therefore, with therapy based on these compounds, disorders associated with dementia, Alzheimer's disease, Parkinson's disease and other pathologies associated with the disease can be prevented and / or treated. neurofibrillary marana. Claim 1: A compound of formula (1) and (2), wherein P represents a 5- or 6-membered heteroaromatic ring containing one or two heteroatoms independently selected from N, O and S, of which at least an atom is nitrogen; R1 is hydrogen; R2 and R3 are independently selected from halogen, nitro, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C0-6 alkyl-C3-6 cycloalkyl, C0-6 alkylaryl, C0-6 alkylheteroaryl, CHO, alkyl ( C0-6) OR4, Oalkyl (C1-6) OR4, alkyl (C0-6) SR4, Oalkyl (C1-6) SR4, (CO) R4, (CO) OR4, O (CO) R4, fluoromethyl, difluoromethyl, trifluoromethyl, fluoromethoxy, difluoromethoxy, trifluoromethoxy, C1-6 alkyl alkyl, C0-6 alkylcyl (C1-6) alkyl CO2R4, Oalkyl (C1-6) CO2R4, O (CO) OR4, Oalkyl (C1-6) COR4 alkyl (C1 -6) COR4, NR4OR5, (C0-6) alkyl NR4R5, Oalkyl (C1-6) NR4R5, alkyl (C0-6) CONR4R5, Oalkyl (C1-6) CONR4R5, Oalkyl (C1-6) NR4 (CO) R5 , (C0-6) NR4 (CO) R5 alkyl, (C0-6) NR4 (CO) NR4R5, O (CO) NR4R5, NR4 (CO) OR5, (C0-6) (SO2) NR4R5, C1 alkyl alkyl -6 (SO2) NR4R5, (C0-6) alkyl NR4 (SO2) R5, Oalkyl (C1-6) NR4 (SO2) R5, alkyl (C0-6) (SO) NR4R5, Oalkyl (C1-6) (SO ) NR4R5, SO3R4, (C0-6) alkyl NR4 (SO2) NR4R5, (C0-6) alkyl NR4 (SO) R5, Oalkyl (C0-6) NR4 (SO) R5, Oalkyl (C0-6) SO2R4, alkyl (C0-6) S O2R4, (C0-6) alkyl SOR4, Oalkyl (C1-6) SOR4 and a group X1R6, in which X1 is a direct bond, O, CONR7R8, SO2NR9R10, SO2R11 or NR12R13; and in which R6 is linked to R8, R10, R11 and R13; R7, R9 and R12 are each independently hydrogen or C1-6 alkyl; R8, R10, R11 and R13 are C1-6 alkyl; R6 is phenyl or a 5, 6 or 7 membered heterocyclic group containing one or two heteroatoms independently selected from N, O and S, where the heterocyclic group may be saturated or unsaturated, or said phenyl or heterocyclic group of 5, 6 or 7 members may optionally be fused with a saturated or unsaturated 5 or 6 membered ring containing atoms independently selected from C, N, O and S and where the phenyl or heterocyclic group may be substituted with one or two substituents between W; m is 0, 1, 2, 3 or 4; n is 0, 1, 2, 3 or 4; R4 is selected from hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, (C0-6) alkyl (C3-6) cycloalkyl, C0-6 alkylaryl, C0-6 alkylheteroaryl, C1-6 alkyl 6) NR14R15 and a 5 or 6 membered heterocyclic group containing one or two heteroatoms independently selected from N, O and S, wherein said heterocyclic group may be optionally substituted with a Y group; R5 is selected from hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, (C0-6) alkyl (C3-6) alkyl, C0-6 alkylaryl, C0-6 alkylheteroaryl and (C1-6 alkyl ) NR14R15 and; wherein R4 and R5 may together form a 4, 5, 6 or 7 membered heterocyclic group containing one or more heteroatoms independently selected from N, O and S, wherein said heterocyclic group may be optionally substituted with a Y group; and wherein any C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, (C0-6) alkyl (C3-6) cycloalkyl, C0-6 alkylaryl and C0-6 alkylheteroaryl defined under R2 to R5 may be substituted with one or more Z groups; R14 and R15 are independently selected from hydrogen, C1-6 alkyl and (C0-6) alkyl (C3-6) alkyl, where R14 and R15 can together form a 5 or 6 membered heterocyclic group containing one or more heteroatoms, independently selected from N, O and S, wherein said heterocyclic group may be optionally substituted with a group Y; W and Z are independently selected from oxo, halogen, nitro, CN, OR16, C1-6 alkyl, C0-6 alkylaryl, (C0-6) alkyl (C3-6) alkyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoromethoxy, difluoromethoxy , trifluoromethoxy, Oalkyl (C1-6) NR16R17, NR16R17, CONR16R17, NR16 (CO) R17, O (CO) C1-6alkyl, (CO) C1-6alkyl, COR16, (SO2) NR16R17, SO2R16, SOR16, ( CO) (C1-6) alkyl NR16R17, (SO2) (C1-6) alkyl NR16R17, a 5- or 6-membered heterocyclic group containing 1 or 2 heteroatoms, independently selected from N, O and S, phenyl and heteroaryl, where the heterocyclic, phenyl or heteroaryl groups may be optionally substituted with a Y group; Y is selected from oxo, halogen, nitro, CN, OR16, C1-6 alkyl, C0-6 alkylaryl, C0-6 alkyl C3-6 cycloalkyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoromethoxy, difluoromethoxy, trifluoromethoxy, Oalkyl (C1-6 ) NR16R17, NR16R17, CONR16R17, NR16 (CO) R17, O (CO) C1-6 alkyl, (CO) C1-6 alkyl, COR16, (SO2) NR16R17, SO2R16, SOR16, (CO) C1-6 alkyl NR16R17, (SO2) C1-6 alkyl NR16R17, phenyl, C0-6 alkylaryl and heteroaryl where the phenyl, C0-6 alkylaryl and heteroaryl groups may be optionally substituted with halogen, nitro, CN, OR16, C1-6 alkyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoromethoxy, difluoromethoxy and trifluoromethoxy; R16 and R17 are independently selected from hydrogen and C1-6 alkyl and where R16 and R17 can together form a 5- or 6-membered heterocyclic group containing one or more heteroatoms, independently selected from N, O and S; as a free base or as a pharmaceutically acceptable salt thereof. Claim 23: A process for the preparation of a compound of formula (1) according to claim 1, comprising: a) reacting a compound of formula (3), wherein L1 is a leaving group such as halogen, for example fluorine, chlorine or bromine, with a compound of formula (4); wherein R1, R2 and m are as defined in claim 1, to form a compound of formula (1); in an appropriate solvent at a temperature between + 10 ° C and + 150 ° C, b) reacting a compound of formula (5) where halo is halogen, for example fluorine, chlorine or bromine, with a compound of formula (4 ); wherein R1, R2 and m are as defined in claim 1 to form a compound of formula (6); in an appropriate solvent at a temperature between + 10 ° C and + 150 ° C; c) reacting a compound of formula (7), wherein R 4 is C 1-6 alkyl, with the appropriate amine HNR 4 R 5, to form a compound of formula (8); which is carried out by; i) reaction of the compound of formula (7) with the appropriate amine R4R5NH in a suitable solvent in the presence of an appropriate reagent at a reaction temperature between 0 ° C and reflux; or ii) the reaction of the compound of the formula (7) with the appropriate amine R4R5NH alone or in a suitable solvent with or without appropriate base at a temperature between -20 ° C and + 150 ° C; d) the reduction of n-oxide in the compound of formula (9), to form a compound of formula (10) by the use of a suitable reagent in a suitable solvent at a temperature between 0 ° C and + 100 ° C. |
| priorityDate | 2002-03-28-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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Total number of triples: 110.