http://rdf.ncbi.nlm.nih.gov/pubchem/patent/AR-047424-A1
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_24e76490bed88751680a5fef9bc73892 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P35-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D413-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D215-54 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D295-155 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D295-155 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61K31-47 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D413-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D215-54 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D215-12 |
| filingDate | 2005-01-17-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_6c6d2a89b2d8658fb1a16f2f627d22ba http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_2ab62a8d3d95464ef69d005de306ded1 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_c805097474ced6246b8d90dd0770daf6 |
| publicationDate | 2006-01-18-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | AR-047424-A1 |
| titleOfInvention | QUINOLINE INTERMEDIARIES AS INHIBITORS OF THIROSINE KINASE RECEPTORS AND THE SYNTHESIS OF THE SAME |
| abstract | Methods of preparing 4-substituted quinoline compounds as intermediates in the preparation of receptor tyrosine kinase inhibitors and intermediates used in such methods. Claim 1: A method of preparing a 4-substituted quinoline compound characterized in that it comprises the step of reacting a compound of the formula (2), with a reagent of formula POLG'3, where LG 'is halo, to provide a compound of the formula (1), where: LG is a leaving group selected from the group consisting of morpholino, o-mesyl, o-tosyl, triflate; LG '' is a leaving group selected from the group consisting of morpholino, o-mesyl, o-tosyl, triflate and halogen; PG is a protective group selected from the group consisting of acyl, CH3OC (O) -, EtOC (O) -, Fmoc, trifluoroacetamide, Troc, Fenoc, benzamide, Teoc, phthalimide, maleimide and 2,5-dimethylpyrrole; A is O, NR or S; R is H, alkyl, alkenyl or alkynyl; and G, R1 and R4 are each independently hydrogen, halogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C2-6 alkenyloxy, C2-6 alkynyloxy, hydroxymethyl, halomethyl, C1-6 alkanoyloxy , C3-8 alkenyloxy, C3-8 alkynyloxy, C2-7 alkanoyloxymethyl, C4-9 alkenyloxymethyl, C4-9 alkyloxymethyl, C2-7 alkoxymethyl, C1-6 alkoxy, C1-6 alkylthio, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl , C1-6 alkylsulfonamide, C2-6 alkenylsulfonamide, C2-6 alkylsulfonamide, hydroxy, trifluoromethyl, trifluoromethoxy, cyano, nitro, carboxy, C2-7 carboalkoxy, C2-7 carboalkyl, phenoxy, phthalimide, phenyl, thiophene, amino hydroxyamino, C 1-4 alkoxyamino, C 1-6 alkylamino, C2-12 dialkylamino, N-alkylcarbamoyl, N, N-dialkylcarbamoyl, N-C4-12 alkyl-N-alkenylamino, N, C6-12 N-dialkenylamino, phenylamino, benzylamino , the group of formula (3),, R9R8-CH-M- (C (R6) 2) kY-, R7- (C (R6) 2) gY-, R7- (C (R6) 2) pM- ( C (R6) 2) kY- or Het- (C (R6) 2) qW- (C (R6) 2-Y-; or R1 and R4 are as defined above Now and G is R2-NH-; or if any of the substituents R1, R4 or G are located on adjacent carbon atoms then they can be taken together as the divalent radical -O-C (R6) 2-O; Y is a divalent radical selected from the group consisting of: - (CH2) a-, -O-, and -NR6-; R7 is -NR6R6, -OR6, -J, -N (R6) 3+, or -NR6 (OR6); M is> NR6, -O-,> N- (C (R6) 2pNR6R6, or> N- (C (R6) 2) p-OR6; W is> NR6, -O- or is a bond; Het is selected from the group consisting of morpholino, thiomorpholino, thiomorpholino S-oxide, S, thiomorpholino S-dioxide, piperidine, pyrrolidine, aziridine, pyridine, imidazole, 1,2,3-triazole, 1,2,4-triazole, thiazole, thiazolidine, tetrazol, piperazine, furan, thiophene, tetrahydrothiophene, tetrahydrofuran, dioxane, 1,3-dioxolane, tetrahydropyran, and the group of formula (4), where Het is optionally mono- or di-substituted on carbon or nitrogen with R6 , optionally mono- or di-substituted on the carbon with hydroxy, -N (R6) 2, or -OR6, optionally mono or di-substituted on the carbon with the monovalent radicals -C (R6) 2) s OR6 or -C (R6) 2) s N (R6) 2, and optionally mono or di-substituted on a carbon saturated with the divalent radicals -O- or -O (C (R6) 2) sO-; R6 is hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 cycloalkyl, C2-7 carboalkyl, C2-7 carboalkoxy, C2-7 carboxyalkyl, phenyl or phenyl optionally substituted with one or more halogens, C1-6 alkoxy, trifluoromethyl, amino, C1-3 alkylamino, C2-6 dialkylamino, nitro, cyano, azide, halomethyl, C2-7 alkoxymethyl, C2-7 alkanoyloxymethyl, C1-6 alkylthio, hydroxy, carboxyl, C2-7 carboalkoxy , phenoxy, phenyl, thiophenoxy, benzoyl, benzyl, phenylamino, benzylamino, C1-6 alkanoylamino or C1-6 alkyl; with the proviso that the alkenyl or alkynyl group is attached to a nitrogen or oxygen atom through a saturated carbon atom; R2, is selected from the group consisting of formulas (5); R3 is independently hydrogen, C1-6 alkyl, carboxy, C1-6 carboalkoxy, phenyl, C2-7 carboalkyl, the group of formula (6), R7- (C (R6) 2) s-; R7- (C (R6) 2) p-M- (C (R6) 2) r-, R8R9-CH-; M- (C (R6) 2) r-; or Het- (C (R6) 2) q-W- (CR6) 2) r-; R5 is independently hydrogen, C1-6 alkyl, carboxy, C1-6 carboalkoxy, C2-7 phenylcarboalkyl, the group of formula (7), R7- (C (R6) 2) s-; R7- (C (R6) 2) p-M- (C (R6) 2) r-, R8R9-CH-; M- (C (R6) 2) r-; or Het- (C (R6) 2) q-W- (CR6) 2) r-; R8, and R9 are each, independently - (C (R6) 2) rNR6R6, or - (C (R6) 2) rOR6; J is independently hydrogen, chlorine, fluorine or bromine; Q is C1-6 alkyl or hydrogen; a = 0 or 1; g = 1-6; k = 0-4; n is 0-1; m is 0-3; p = 2-4; q = 0-4; r = 1-4; s = 1-6; u = 0-4 and v = 0-4, where the sum of u + v is 2-4; x = 0-3; y = 0-1; z = 0-3; or a salt thereof. |
| priorityDate | 2004-01-16-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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