http://rdf.ncbi.nlm.nih.gov/pubchem/patent/ES-2363795-T3
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_27a71ddaaa2f5a8c228fc6cb3f3b3098 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D471-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P9-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P9-08 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-28 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P29-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P27-14 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P31-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P35-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P39-02 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P37-08 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P43-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P11-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P11-02 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P11-06 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P13-12 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P17-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P17-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P17-06 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P19-02 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-02 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-22 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-24 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-18 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P1-04 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D471-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61K31-437 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D519-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61P29-00 |
| filingDate | 2006-09-29-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| grantDate | 2011-08-16-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_08c2b7720d0892cff5582ecd1311f89a http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_f951048a7d471e985526994f420c6977 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_848bb0f7804c15d64e57eba73e1011e6 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_03f1b413cbb7351069318afdb89a3eef http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_c32d827f1f519c8331a7722a452c3301 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_2cb7ae019cf0f079b4ca33654748b07b http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_e634019fa0d7b889c5fae623c9fd02b7 |
| publicationDate | 2011-08-16-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | ES-2363795-T3 |
| titleOfInvention | PIRAZOLO COMPOUNDS [3,4-B] PIRIDINE, AND ITS USE AS PDE4 INHIBITORS. |
| abstract | A compound of the formula (I) or salt thereof (in particular, a pharmaceutically acceptable salt thereof): wherein: R 1 is C 1-3 alkyl, C 1-3 fluoroalkyl, or -CH 2CH 2OH; R 2 is a hydrogen atom (H), methyl, ethyl, n-propyl, isopropyl, n-butyl, C 1-2 fluoroalkyl, cyclopropyl, cyclobutyl, (cyclopropyl) methyl-, cyano (-CN), or -CH 2OH R 3 is optionally substituted C 4-7 cycloalkyl or optionally substituted C 5-7 mono-unsaturated cycloalkenyl or an optionally substituted heterocyclic group of the sub-formula (aa), (bb) or (cc); in which n 1 and n 2 are independently 1 or 2 and in which Y is O, S, SO 2 or NR 10; where R 10 in a hydrogen atom (H), methyl, C (O) NH2, C (O) -methyl, or fluoroalkyl C (O) -C 1; or R 3 is a bicyclic group of the sub-formula (ee): and in which, when R 3 is optionally substituted C4-7 cycloalkyl, then R 3 is C4-7 cycloalkyl optionally substituted on a ring carbon with one or two substituents that are independently: oxo (= O); OH; methoxy; C1 fluoroalkoxy ;. NH2; C1-2 alkyl; C1 fluoroalkyl; -CH2OH; -CH (Me) OH; -CH2CH2OH; -CH2NH2; -C (O) OH; - C (O) NHR24 in which R 24 is H or methyl; -C (O) R 25 in which R 25 is methyl; fluoro; hydroxyimino (= N-OH); or (C1-2 alkoxy) imino (= N-OR 26 in which R 26 is C1-2 alkyl); and wherein any OH, methoxy, fluoroalkoxy or NH 2 substituent is not substituted on the carbon of the R 3 ring attached (bonded) to the -NH- group of the formula (I); and wherein, when R 3 is the optionally substituted heterocyclic group of the sub-formula (aa), (bb) or (cc), then R 3 is the heterocyclic group of the sub-formula (aa), (bb) or (cc) optionally substituted on a ring carbon with one or two substituents that are independently oxo (= O), OH or methyl; and wherein any OH substituent is not substituted on the carbon of the R 3 ring attached (bonded) to the -NH- group of the formula (I) and is not substituted on any carbon of the R 3 ring attached to the Y group of the heterocyclic group (aa), (bb) or (cc); and wherein, when R 3 is optionally substituted mono-unsaturated C 5-7 cycloalkenyl, then the cycloalkenyl is optionally substituted on a ring carbon with a substituent that is fluorine or methyl, and the carbon of the R 3 ring attached to the -NH- group of the formula (I) does not participate in the cycloalkenyl double bond; provided that: when R 3 is the heterocyclic group of the sub-formula (aa) and Y is NR 10, then R 10 is not C (O) -methyl, or C (O) - C 1 fluoroalkyl; and when R 3 is the heterocyclic group of the sub-formula (bb), and Y is NR 10, then R 10 is not methyl; and when R 3 is the heterocyclic group of the sub-formula (cc), then Y is O S, SO 2 or NR 10 in which R 10 is H or methyl; and wherein: when R 3 is optionally substituted C4-7 cycloalkyl, then any substituent -C (O) NHR 24 or -C (O) R 25 in a ring carbon is: at position 3 of a cyclobutyl ring R 3 ; or in position 3 or 4 of a cyclopentyl ring R 3; or at position 4 of a cyclohexyl ring of R 3; or at position 3, 4, 5 or 6 of a cycloheptyl ring R 3 (where, in this connection, position 1 of the cycloalkyl ring R 3 is considered to be the point of connection to -NH- in the formula ( I), which is the ring atom that connects to -NH- in formula (I)); and wherein: when R 3 is optionally substituted C4-7 cycloalkyl, then any substituent OH, methoxy, fluoroalkoxy, - CH2OH -CH (Me) OH, -CH2CH2OH, -CH2NH2, or -C (O) OH on a carbon ring is: in position 3 of a cyclobutyl ring R 3; or in position 3 or 4 of a cyclopentyl ring R 3; or at position 3, 4 or 5 of a cyclohexyl ring R 3; or at position 3, 4, 5 or 6 of a cycloheptyl ring of R 3; and and wherein: when R 3 is the heterocyclic group of the sub-formula (aa), (bb) or (cc), then any OH substituent on a ring carbon is: at position 5 of a heterocyclic group R 3 of six elements of the sub-formula (cc) in which n 2 is 1; or at position 5 or 6 of a heterocyclic group R 3 of seven elements of the sub-formula (cc) in which n 2 is 2; or at position 6 of a heterocyclic group R 3 of seven elements of the sub-formula (bb) in which n 1 is 2 (in which, in this connection, position 1 of the heterocyclic ring R 3 is considered to be the point of connection to -NH- in formula (I), which is the atom of the ring that connects to -NH- in formula (I), and the rest of the ring positions are numbered afterwards so that the ring heteroatom takes the lowest possible number); and wherein: R a is a hydrogen atom (H), methyl or ethyl; R b is a hydrogen (H) or methyl atom; wherein, when R b is methyl, then R a is methyl and R 2 is a hydrogen atom (H); R 4 is a hydrogen atom (H), methyl, ethyl, n-propyl, -C (O) -Me, or -C (O) -C 1 fluoroalkyl; provided that when R 4 is -C (O) -Me or -C (O) -fluoroalkyl C 1, then R 5 is -CH 2-Ar; and R 5 is: - C (O) - (CH 2) n-Ar, -C (O) -Het, -C (O) -C 1-6 alkyl, -C (O) - C 1 fluoroalkyl, - C (O) - (CH 2) 2-C (O) - NR 15b NR 15b, -C (O) -CH 2-C (O) -NR 15b NR 15b, - C (O) -NR 15b - ( CH 2) m 1 -Ar, -C (O) -NR 15b -Het, -C (O) -NR 15b -C 1-6 alkyl, - C (O) -NR 5a R 5b, -S (O) 2 - (CH 2) m 2 -Ar, -S (O) 2-Het, -S (O) 2- C 1-6 alkyl, or -CH 2-Ar; in which n and m 1 and m 2 are independently 0, 1 or 2; and Ar, independent of another Ar, has the sub-formula (x) or (z), in which (z) is connected to a ring carbon: or R 4 and R 5 taken together are - (CH 2) p 1 - (optionally substituted), or - (CH2) 2-X 5 - (CH 2) 2-, or -C (O) - (CH 2) p 2 -, or - C (O) -N (R 15) - (CH2) p 3 -, in which: X 5 is NR 17 and p 1 is 4, 5 or 6, and p 2 is 3, 4 or 5, and p 3 is 2 or 3; or NR 4 R 5 is of the sub-formula (y), (y1), (y2) or (y3) in which p 4 is 1 or 2: and in which, when R 4 and R 5 taken together is - (CH 2) p 1 -, then the NR 4 R 5 ring is optionally substituted on the carbon atom of the ring of position 3 and / or on the carbon atom of the ring of position 4 (in which the Ring nitrogen is position 1) by one or two substituents that are independently: phenyl; phenyl substituted by one or two (for example one) substituents that are independently methyl or CF3 or fluorine or chlorine or methoxy or difluoromethoxy; phenyl-C (O) -; phenyl-C (O) - whose phenyl ring is substituted by one or two (for example one) substituents that are independently methyl or fluorine or chlorine or methoxy: benzyloxy; phenyloxy; phenyloxy whose phenyl ring is substituted by one or two (for example one) substituents that are independently methyl or CF3 or fluorine or chlorine or methoxy or difluoromethoxy; a heteroaromatic ring of five elements that are oxazolyl, isoxazolyl, thiazolyl, 1,2,4-oxadiazolyl, 1,3,4oxadiazolyl, furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl; triazolyl or tetrazolyl, wherein the five-element heteroaromatic ring is optionally substituted on a ring carbon by a substituent that is methyl or ethyl or isopropyl or t-butyl or phenyl or pyridinyl and / or is optionally substituted on a ring nitrogen by a substituent that is methyl or ethyl or isopropyl or t-butyl or phenyl; -CH 2- (pyrrol-1-yl); a six element heteroaromatic ring which are pyridinyl, pyrimidinyl, pyrazinyl or pyridazinyl, in which the six element heteroaromatic ring is optionally substituted on a carbon of the ring either by a methyl substituent or by an OH substituent, which is substituted by a ring carbon attached to a ring nitrogen (including the keto tautomer thereof); C 1-2 alkyl (for example, methyl); cyano (-CN); or (4-hydroxyphenyl) -C (O) -CH 2-CH 2-; or alternatively when R 4 and R 5 taken together is - (CH 2) p 1 - and p 1 is 5, then the NR 4 R 5 ring is optionally substituted on the carbon atom of the 4-position ring by two substituents that when taken together are -OC (O) -N (benzyl) -CH 2-; or alternatively when R 4 and R 5 taken together are - (CH 2) p 1 - and p 1 is 4 or 5, then the NR 4 R 5 ring is optionally substituted on the carbon atoms of the position 3 ring and position 4 by two substituents that when taken together are = CH-CH = CH-CH =; and in which, in the sub-formula (x), and independently in the sub-formula (y): A is CR 6A or nitrogen (N), B is CR 6B or nitrogen (N), D is CR 6D or nitrogen (N), E is CR 6E or nitrogen (N), F is CR 6F or nitrogen (N), in which, R 6A, R 6B, R 6D, R 6E and R 6F are independently: a hydrogen atom (H), a halogen atom; C1-6 alkyl (for example, C1-4 alkyl or C1-2 alkyl); C1-4 fluoroalkyl (for example, C1-2 fluoroalkyl); C3-6 cycloalkyl; C1-4 alkoxy (for example C1-2 alkoxy); C1-2 fluoroalkoxy; C3-6 cycloalkyl oxy; -C (O) R 16; -C (O) OR 30; -S (O) 2-R 16 (for example, C1-3-S (O) 2-) alkyl; R 16 -S (O) 2-NR 15 - (for example C1-3-S (O) 2-NH- alkyl); R 12 R 13 N-S (O) 2-; C1-2-C (O) alkyl - R 15 N-S (O) 2-; C 1-4 alkyl (O) -, Ph-S (O) -, R 12 R 13 N-C (O) -; -NR 15 -C (O) R 16; R 7 R 8 N; nitro (-NO2); OH (including any tautomer thereof); C1-4 alkoxy methyl; C1-4 alkoxy ethyl; C1-2-S (O) 2-CH2- alkyl; R 12 R 13 N-S (O) 2-CH2- ;. C1-2 alkyl -S (O) 2-NR 15 -CH2-; -CH2-OH; -CH2CH2-OH; -CH2-NR 7 R 8; -CH2-CH2-NR 7 R 8; -CH2-C (O) OR 30; -CH2-C (O) -NR 12 R 13; -CH2-NR 15 -C (O) C1-3 alkyl; - (CH2) n 14 -Het 1 in which n 14 is 0 or 1; cyano (-CN); Ar 6; 1-pyrrolyl; or phenyl, pyridinyl or pyrimidinyl, wherein the phenyl, pyridinyl or pyrimidinyl are independently optionally substituted by one or two substituents that are independently fluorine, chlorine, C1-2 alkyl, fluoroalkyl C1, C1-2 alkoxy or fluoroalkoxy C1; 20 provided that R 6A, R 6B, R 6D, R 6E and R 6F cannot independently be a chlorine, bromine or iodine atom (and optionally cannot be a fluorine atom) when they are substituted on a carbon of the ring that is attached to a nitrogen of |
| priorityDate | 2005-09-29-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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