http://rdf.ncbi.nlm.nih.gov/pubchem/patent/AR-052660-A1
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_3b70512b2076a2759fccaecf9fe962d5 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P3-10 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P35-02 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P37-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P35-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P1-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61K31-44 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P31-18 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P43-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D231-40 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D231-14 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P11-02 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D401-14 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D401-12 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61K31-4545 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P9-06 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P13-12 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P9-10 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P19-10 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P9-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P21-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D409-12 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P19-02 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P7-06 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P19-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D405-14 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D405-12 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P17-06 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D417-14 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-08 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-16 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D413-12 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P29-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-28 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-32 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P31-12 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P31-10 |
| filingDate | 2006-01-19-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 2007-03-28-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | AR-052660-A1 |
| titleOfInvention | PIRAZOL DERIVATIVES TO INHIBIT THE CDK'S AND GSK'S |
| abstract | The compounds have activity as inhibitors of cdk kinase (such as cdk1 or cdk2) and glycogen synthase kinase-3. Claim 1: A compound of the formula (1), its salt, tautomer, N-oxide or solvate wherein: R1 is selected from: (a) 2,6-dichlorophenyl; (b) 2,6-difluorphenyl; (c) A 2,3,6-trisubstituted phenyl group wherein the substituents of the phenyl group are selected from F, Cl, methyl and methoxy, (d) an R0 group, (e) an R1a group; (f) a group R1b; (g) a group R1c; (h) a group R1d; and (j) 2,6-difluorophenylamino; R0 is a carbocyclic or heterocyclic group having 3 to 12 ring members, or a C1-8 hydrocarbyl group optionally substituted with one or more substituents selected from F, hydroxy, cyano, C1-4 hydrocarbyloxy, amino, mono or di-hydrocarbylamino C1-4 and carbocyclic or heterocyclic groups having between 3 and 12 ring members and where 1 or 2 C atoms of the hydrocarbyl group may optionally be replaced by an atom or group selected from O, S, NH, SO, SO2; R1a is selected from cyclopropyl-cyano-methyl, furyl; benzoisoxazolyl; methyl isoxazolyl; 2-monosubstituted and 2,6-disubstituted phenyl where the substituents in the phenyl portion are selected from methoxy, ethoxy, F, Cl and difluoromethoxy; provided that R1a is not 2,6-difluorophenyl or 2,6-dichlorophenyl; R1b is selected from tetrahydrofuryl, and monosubstituted and disubstituted phenyl where the substituents on the phenyl portion are selected from F, Cl, methoxy, ethoxy and methylsulfonyl; R1c is selected from benzoisoxazoyl; 5-membered heteroaryl rings with one or two heteroatoms selected from O and N and 6-membered heteroaryl rings with one or two N heteroatoms in the ring, the heteroaryl rings may, in each case, optionally be substituted with methyl, F, Cl, or trifluoromethyl; and the phenyl can be substituted with 1, 2, or 3 substituents selected from Br, Cl, F, methyl, trifluoromethyl, ethoxy, methoxy, methoxyethoxy, methoxymethyl, dimethylaminomethyl and difluoromethoxy; provided that R1a is not 2,6-difluorophenyl; R1d is a R1e-CH (CN) group - where R1e is a carbocyclic or heterocyclic group having 3 to 12 ring members; R2a and R2b are each H or methyl; and where: A when R1 is (a) 2,6-dichlorophenyl and R2a and R2b are both H, then R3 can be selected from: (i) a group of formula (2), where R9 is selected from C (O) NR5R6, C (O) -R10 and 2-pyrimidinyl wherein R10 is a C1-4 alkyl group optionally substituted with one or more substituents chosen from F, Cl, cyano and methoxy; and R11 where R11 is a C1-4 alkyl group optionally substituted with one or more substituents chosen from F, Cl, and cyano; (ii) a group of formula (3) wherein R12 is C2-4 alkyl; a group of formula (4) wherein R13 is selected from methylsulfonyl, 4-morpholino, 4-thiomorpholino, 1-piperidino, 1-methyl-4-piperazino and 1-pyrrolidino; (iii) a substituted 3-pyridyl or 4-pyridyl group of formula (5) wherein the R14 group is meta or para with respect to the bond labeled with an asterisk and is selected from methyl, methylsulfonyl, 4-morpholino, 4-thiomorpholino, 1-piperidino, 1-methyl-4-piperazino, 1-pyrrolidino, 4-piperidinyloxy, 1-alkoxy-C1- 4 -carbonyl-piperidin-4-yloxy, 2-hydroxyethoxy and 2-methoxyethoxy; and (v) a group selected from 2-pyrazinyl, 5-pyrimidinyl, cyclohexyl, 1,4-dioxa-spiro [4.5] decan-8-yl (4-cyclohexanone ethylene glycol ketal), 4-methylsulfonylamino-cyclohexyl, tetrahydrothiopyran-4 -yl, 1,1-dioxo-tetrahydrothiopyran-4-yl, tetrahydropyran-4-yl, 4,4-difluorocyclohexyl and 3,5-dimethylisoxazol-4-yl; and B when R1 is (b) 2,6-difluorophenyl and R2a and R2b are both H, then R3 can be selected from: (vi) 1- methyl-piperidin-3-yl; 4- (2-dimethylaminoethoxy) -cyclohexyl; and an N-substituted 4-piperidinyl group wherein the N substituent is selected from cyanomethyl and cyanoethyl; and (vii) a group of formula (4) where R13 is as defined above; and C when R1 is (c) a 2,3,6-trisubstituted phenyl group where the substituents of the phenyl group are selected from F, Cl, methyl and methoxy; and R2a and R2b are both H, then R3 can be selected from groups (ii), (xi), (xii) and (xiii) as defined herein; and (viii) 4-piperidinyl and 1-methyl-4-piperidinyl; (ix) tetrahydropyran-4-yl; and (x) a group of formula (7) wherein R4 is C1-4 alkyl; D when R1 is (d) a group R0, where R0 is a carbocyclic or heterocyclic group having 3 to 12 ring members; or a C1-8 hydrocarbyl group optionally substituted with one or more substituents selected from F, hydroxy, cyano, C1-4 hydrocarbyloxy, amino, mono or di-hydrocarbonylamino C1 and carbocyclic or heterocyclic groups having between 3 and 12 ring members and where 1 or 2 C atoms of the hydrocarbyl group may be replaced by an atom or group selected from O, S, NH, SO, SO2; then R3 can be selected from: (xi) a group of formula (8) where R7 is: unsubstituted hydrocarbyl other than C1-4 alkyl; C1-4 substituted hydrocarbyl bearing one or more substituents chosen from F, Cl, hydroxy, methylsulfonyl, cyano, methoxy, NR5R6, and saturated carbocyclic or heterocyclic rings of 4 to 7 members containing up to 2 ring members of a heteroatom selected from O , N and S; an NR5R6 group where R5 and R6 are selected from H and C1-4 alkyl, C1-2 alkoxy and C1-2 alkoxy-C1-4 alkyl, provided that no more than one of R5 and R6 is C1-2 alkoxy, or NR5R6 it forms a 5 or 6 membered heterocyclic ring containing 1 or more annular members of a heteroatom selected from O, N and S, and the heterocyclic ring is optionally substituted with one or more methyl groups; a 5 or 6 membered heteroaryl group containing 1 or 2 ring members of a heteroatom selected from N, S and O optionally substituted with methyl, methoxy, F, Cl, or an NR5R6 group; a phenyl group optionally substituted with methyl, methoxy, F, Cl, cyano or an NR5R6 group; C3-6 cycloalkyl; and a saturated 5- or 6-membered heterocyclic group containing 1 or 2 annular members of a heteroatom selected from N, S and O and the heterocyclic group that is optionally substituted with one or more methyl groups; and (xii) a group of formula (3) wherein R12a is C1-4 alkyl substituted with one or more substituents chosen from F, Cl, C3-6 cycloalkyl, C4-6 oxocycloalkyl, cyano, methoxy and NR5R6, provided there is, at least two atoms of C between the atom of O to which R12 is attached and a group NR5R6 when present and E when R1 is (e) a group R1a, and R2a and R2b are both H, then R3 can be (xiii ) a group of formula (9) and F when R1 is (f) a group R1b and R2a and R2b are both H, then R3 can be (xiv) a methyl group; and G when R1 is (g) a group R1c and R2a and R2b are both H, then R3 can be (xv) a group of formula (10) and H when R1 is (h) a group R1d, then R3 is a group -Y-R3a where Y is a C1-3 long alkylene bond or chain and R3a is selected from H and carbocyclic and heterocyclic groups having 3 to 12 ring members; J when R1 is (j) 2,6-dichlorophenylamino, and R2a and R2b are both H, then R3 can be methyl; and K when R1 is 2,6-dichlorophenyl and (k) R2a is methyl and R2b is H, or (l) R2a is H and R2b is methyl, then R3 can be a 4-piperidine group; or its salts, tautomers, solvates and N-oxides. |
| priorityDate | 2005-01-21-04:00^^<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: 101.