http://rdf.ncbi.nlm.nih.gov/pubchem/patent/AR-043692-A1
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_cf32b60391b469c41e86c353437f5751 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-02 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P25-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P29-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D487-04 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61P29-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D519-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D487-04 |
| filingDate | 2004-02-04-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 2005-08-10-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | AR-043692-A1 |
| titleOfInvention | 2-CYANOPIRROLOPIRIMIDINAS AND ITS PHARMACEUTICAL USES |
| abstract | Pyrrolopyrimidines; its preparation, its use as pharmaceuticals, pharmaceutical compositions containing them, and the use of said compound for the manufacture of a pharmaceutical preparation for the treatment of neuropathic pain and a method for the treatment of said disease in animals, especially in humans. Claim 1: A pyrrolopyrimidine of the formula (1) wherein Y represents - (CH2) tO- or - (CH2) rS-, p is 1 or 2, r is 1, 2 or 3, t is 1, 2 or 3 , R1 represents: (h) phenyl which is unsubstituted or mono-, di- or trisubstituted by (alpha) halogen, carboxy, alkoxy, nitro, alkyl-C (O) -NH-, cycloalkyl-C (O) - NH-, alkyl-C (O) -N (alkyl) -, formyl, alkyl-C (O) -, alkyl-S (O) 2-NH-, CF3-alkyl-S (O) 2-NH-, pyrrolidin carbonyl, piperidinylcarbonyl, morpholinylcarbonyl, N-alquilpiperazinilcarbonilo, piperidinyl, 1- (alkylcarbonyl) piperidinyl, 1,2,3,6-tetrahydropyridyl, 1,2,3,6-tetrahydropyridyl alkylcarbonyl, piperazinyl, alkylpiperazinyl, alquilcarbonilpiperazinilo, cicloalquilcarbonilpiperazinilo, alcoxicarbonilpiperazinilo , alkyl-SO2-piperazinyl, diazacycloheptyl, alkylcarbonyldiazacycloheptyl, 2-oxo-1-pyrrolidinyl, 3,3-di-alkyl-2-oxo-1-pyrrolidinyl; (beta) R3-alkyl wherein R3 represents hydrogen, hydroxy, carboxy, alkylthio-N (alkyl) -, alkyl-NH-1-pyrrolidinyl, 1-piperidinyl, 4-alkyl-1-piperazinyl carbonyl, 2,4-dioxa -5,5- (dialkyl) -oxazolidin-3-yl, R4R5N-C (O) -, wherein R4 and R5 independently of each other represents hydrogen or alkyl; (gamma) R6R7N-C (O) - wherein R6 and R7 independently of each other represent hydrogen, alkyl, cycloalkylalkyl, CF3alkyl or pyridylalkyl; (i) pyridyl, which is unsubstituted or mono-, di- or trisubstituted by halogen; (j) pyrimidinyl; (k) indolyl, which is mono- or disubstituted by C-alkyl (O) -NH-alkyl; (l) 2- (alkyl) -benzothiazolyl; (m) a radical of the sub-formula (2) wherein R8 is hydrogen, halogen or alkyl, R9 is hydrogen or alkyl, and m is 1, 2, 3 or 4; or (n) a radical of the sub-formula (3) wherein R 10 is hydrogen, halogen or alkyl, R 11 is hydrogen or alkyl, and n is 1, 2, 3 or 4; R 2 represents alkyl, which is unsubstituted or substituted by cycloalkyl, which is unsubstituted or mono- or disubstituted by halogen, or phenyl, which is mono- or disubstituted by halogen; provided that R2 does not represent 1,1-dimethylethyl if Y is O and R1 is selected from 3-pyridyl, 4-pyridyl, 5-chloro-3-pyridyl, 6-chloro-3-pyridyl, 2-chloro-4-pyridyl , 2-trifluoromethyl-4-pyridyl, 2-difluoromethyl-4-pyridyl, 4-acetyl-1-piperazinyl-phenyl, 4-methyl-1-piperazinyl-methyl-phenyl, and provided R2 does not represent 1,1-dimethylethyl , if Y is S and R1 is 4-pyridyl; or Y is - (CH2) j- or -CH = CH-, j is 1 or 2; p is 1 or 2, R1 represents (c) thienyl, thiazolyl, 1-piperidinylcarbonyl, or (d) phenyl which is unsubstituted or mono-, di- or trisubstituted by: (i) alkoxy, H2N-C ( O) -, 4- (alkylcarbonyl) 1-piperazinyl, 2-oxo-1-pyrrolidinyl, or halogen; (v) R12-OC (O) -, where R12 is hydrogen or alkyl, or (vi) R13NH-, where R13 represents hydrogen or a radical R14-alkyl-Z-, where Z is CO, SO or SO2 and R14 denotes hydrogen, trifluoromethyl or alkoxy, (vii) R15-alkyl, wherein R15 denotes hydrogen, hydroxy, alkoxy, 1-pyrrolidinyl, 2-oxo-1-pyrrolidinyl, imidazolidin-2,5-dion-1-yl, 5,5-di-alkyl-oxazolidin-2,4-dion-3-yl or alkyl-N (R16) -, wherein R16 represents hydrogen or alkyl; and R2 represents: (d) alkyl, which is unsubstituted or substituted by alkenyl, indanyl, cycloalkyl which is unsubstituted or mono- or disubstituted by halogen or alkyl, cycloalkenyl, phenyl, which is unsubstituted or mono- or disubstituted by halogen or by alkyl; (e) cycloalkyl; or (f) alkylcarbonyl; provided that, if Y is CH2, R1 represents 4-chlorophenyl and p is 1, R2 does not denote 1,1-dimethylethyl, 1-methyl ethyl, cyclopropyl, cyclohexyl, 2-methyl-propyl or 2- ethyl-propyl; provided that R2 does not represent 1,1-dimethylethyl, if p is 1, Y is CH2 and R1 represents thienyl, phenyl, methoxyphenyl, propoxyphenyl, 4-fluorophenyl, 4- methylphenyl, 4-ethylphenyl, 4-butylphenyl, hydroxymethylphenyl, 4- (5,5-dimethyl-oxazolidin-2,4-dion-3-yl-methyl) -phenyl, 4- (methylsulfonylamino) -phenyl, 4- (n-butyl-sulfonylamino) -phenyl, 4- (ethylsulfonylamino) - phenyl, 4- (n-propylsulfonylamino) -phenyl, 4- (iso-propylsulfonylamino) -phenyl, 4-aminophenyl, 4- (acetylamino) -phenyl, 4- (butanoylamino) -phenyl or 4- (diethylaminomethyl) -phenyl; and provided that R2 does not represent 1-methylethyl, if p is 1, Y is CH2 and R1 represents phenyl which is not substituted or substituted by 4-acetyl-1-piperazinyl; Y is - (CH2) f-, f is 1 or 2; p is 1, R 1 represents (d) 1,2,3,6-tetrahydropyrid-1-yl, alkyl-1,2,3,6-tetrahydropyrid-1-yl, di-alkyl-1,2,3,6 -tetrahydropyrid-1-yl, halo-1,2,3,6-tetrahydropyrid-1-yl, phenyl-1,2,3,6-tetrahydropyrid-1-yl, imidazolyl, alkyl-imidazolyl, di-haloimidazolyl, imidazolidin -2,5-dion-1-yl, 5,5-dila-alkyl-oxazolidin-2,4-dion-3-yl, alkyl-imidazolidin-2,5-dion-1-yl, trifluoromethyl-3,4-pyrrolin -1-yl, pyrrolidinyl, alkyl1-pyrrolidinyl, di-alkyl-pyrrolidinyl, alkoxy-pyrrolidinyl, alkyl-2-oxo-1-pyrrolidinyl, di-alkyl2-oxo-1-pyrrolidinyl, halo1-pyrrolidinyl, di-halo1-pyrrolidinyl , di-halo 1-piperidinyl, triazolyl, nitro triazolyl, phenyl-imidazolyl, tetrazolyl, benzo [b] imidazolyl, (1- (alkyl-SO2) -4-piperidinyl) -2,3-dihydro-2-oxo-benzo [b] imidazolyl, 3- (alkylcarbonyl-4-piperidinyl) -2,3-dihydro-2-oxo-benzo [b] imidazolyl, indolyl, halo1-indolyl, 1,3-dihydro-2-isoindolyl, 2,3 -dihydro-1-indolyl, 2,3-dihydro-2-oxo-benzo [b] thiazolyl, di-alkoxy 1,2,3,4-tetrahydroquinoline, alco xi-1,2,3,4-tetrahydroisoquinoline; (b) a radical of the substructure (4) that is attached to the molecule through a nitrogen atom, where X is -O-, - (CH2) s-CR17R18- or -NR18, where s is 0 , 1 or 2, R17 and R18 are independently selected from hydrogen, halogen, hydroxy, alkyl, phenylalkylcarbonyl, carbamoyl, N-phenylcarbamoyl, cyano, pyridyl, piperidinyl and phenyl which is unsubstituted or mono- or disubstituted by halogen or alkoxy, or if X is CR17R18, R17 and R18 together form an oxo group or a HO-C (O) -CH = group, and R23, R24, R25 and R26 are independently selected from hydrogen or alkyl; (c) a radical of the substructure (5) which is attached to the molecule through a nitrogen atom, where k is 0, 1 or 2, A is CH2 or a bond, B is CH2 or carbonyl, D is CH2 or carbonyl, E is CH2 or NR22, G is CH2 or a bond, Q is CH2 or carbonyl, T is CH2 or NR29, R19 represents hydrogen, alkyl, phenylalkyl, alkylcarbonyl or alkyl-SO2-, R22 is hydrogen or alkyl and R29 is phenyl; (d) a radical of the substructure (6) which is attached to the molecule through a nitrogen atom, and wherein R27 is alkyl or alkylcarbonyl and R28 is hydrogen, alkoxy or halogen; or (e) NR2R21, wherein R20 and R21 are independently selected from hydrogen, alkyl, cycloalkyl which is unsubstituted or mono- or disubstituted by hydroxy; and phenyl that is unsubstituted or mono- or disubstituted by 1,2,3-thiadiazolyl, provided that neither R20 nor R21 can represent hydrogen at the same time; and R2 denotes alkyl, which is unsubstituted or substituted by cycloalkyl which is unsubstituted or mono- or disubstituted by halogen; or phenyl, which is mono- or disubstituted by halogen; provided that R2 does not represent 1,1-dimethylethyl if (g) R1 is benzo [b] imidazol-1-yl, 1-imidazolyl, 4,5-dichloro-1-imidazolyl, 2- (C1-4 alkyl) -1 -imidazolyl, imidazolidin-2,5-dion-1-yl, 5,5-dimethyl-oxazolidin-2,4-dion-3-yl, 1H-1,2,3-triazol-1-yl, 2H-1 , 2,3-triazol-2-yl, 3-nitro-1H-1,2,4-triazol-1-yl, 2H-tetrazol-2-yl or 1H-tetrazol-1-yl, or if R1 is a radical of the substructure (6), R23 to R26 are hydrogen, X is NR18 and R18 is hydrogen, methyl, ethyl, acetyl, 4-pyridyl, 1-piperidinyl, phenyl, methoxyphenyl, ethoxyphenyl, fluorophenyl or chlorophenyl; (h) R1 is a radical of the substructure (6), R23 to R26 are hydrogen, X is - (CH2) s-CR17R18-, s is 0, and R17 and R18 are selected from hydroxyl and phenyl which is monosubstituted by chlorine or R17 and R18 are selected from hydrogen, methoxyphenyl and N-phenylcarbamoyl; or (i) R1 is a radical of the substructure (5), k is 1, A is a bond, E is NR22, R22 is hydrogen, G, Q and T are CH2, B and D are carbonyl and R19 is methyl, n-propyl or iso-butyl; provided that R2 does not represent 2-methylpropyl, if R1 is a substructure radical (5), k is 1, A is a bond, E is NR22, R22 is hydrogen, G, Q and T are CH2, B and D are carbonyl and R19 is methyl, or if R1 is a radical of the substructure (6), R23 to R26 are hydrogen, X is - (CH2) s-CR17R18-, s is 0, and R17 and R18 are selected from hydrogen and phenyl which is monosubstituted by methoxy; and provided that R2 does not represent 1-methylethyl, if R1 is a radical of the substructure (6), R23 to 26 are hydrogen, X is NR18 and R18 is methoxyphenyl or ethoxyphenyl, or X is CR17R18 and R17 and R18 are selected from hydrogen and methoxyphenyl; or an N-oxide or a tautomer thereof, or a salt of said pyrrolopyrimidine, its N-oxide or its tautomer. |
| priorityDate | 2003-02-06-04:00^^<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: 53.