http://rdf.ncbi.nlm.nih.gov/pubchem/patent/AR-069715-A1
Outgoing Links
Predicate | Object |
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assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_eccd894c99fea2d1c0c8735872bb2309 |
classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D401-04 |
filingDate | 2008-12-17-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_19fc0a8a394a71196adf36d1972b3e6c http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_04e2e09f552e1bed855ce0d5e748d3e0 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_3d630df8e0978f99858e02c7a12f6d25 |
publicationDate | 2010-02-10-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
publicationNumber | AR-069715-A1 |
titleOfInvention | PROCESS TO PREPARE TETRAHYDROQUINOLINE DERIVATIVES AND OBTAINING INTERMEDIARIES OF SUCH PROCESS ENRIQUECIDOS ENANTIOMERICAMENTE ENRIQUECIDOS. |
abstract | Process for preparing enantiomerically enantiomerically pure tetrahydroquinoline derivatives by reacting a chiral dihydropyran methylamine C with an aldehyde B and an aniline A in a multicomponent synthesis in a single vessel in the presence of a protonic acid or Lewis acid with an appropriate solvent. Claim 1: Process for the manufacture of an enantiomerically enriched or pure compound, characterized in that it responds to formula (1), wherein Ra denotes Hal, cyano, COOH, COOA, A, CF3; R1 denotes H, A, aryl, Het, Hal, - (CY2) n-SA, - (CY2) n-SCF3, - (CY2) n-SCN, - (CY2) n-CF3, - (CY2) n- OCF3, R, cycloalkyl, -SCH3, -SCN, -CF3, -OCF3, -OA, - (CY2) n-OH, - (CY2) n-CO2R, - (CY2) n-CN, - (CY2) n -Hal, - (CY2) n-NR2, (CY2) n-OA, (CY2) n-OCOA, -SCF3, (CY2) n-CONR2, - (CY2) n-NHCOA, - (CY2) n-NHSO2A , SF5, Si (CH3) 3, CO- (CY2) n-CH3, - (CY2) nN-Pirolidon, (CH2) nNRCOOR, NRCOOR, NCO, (CH2) nCOOR, NCOOR, (CH2) nOH, NR (CH2 ) nNR2, C (OH) R2, NR (CH2) nOR, NCOR, (CH2) nAr, (CH2) nHet, (CH2) nR1, (CH2) nX (CH2) nAr, (CH2) nX (CH2) nHet, (CH2) 2CONR2, XCONR (CH2) nNR2, N [(CH2) nXCOOR] CO (CH2) nAr, N [(CH2) nXR] CO (CH2) nAr, N [(CH2) nXR] CO (CH2) nXArile, N [(CH2) nXR] SO2 (CH2) nAr, N [(CH2) nNRCOOR] CO (CH2) nAr, N [(CH2) nNR2] CO (CH2) nAr, N [(CH2) nNR2] CO (CH2) nNRAr, N [(CH2) nNR2] SO2 (CH2) nAr, N [(CH2) nXR] CO (CH2) nHet, N [(CH2) nXR] CO (CH2) nXHet, N [(CH2) nXR] SO2 ( CH2) nHet, N [(CH2) nNRCOOR] CO (CH2) nHet, N [(CHö9nNR2] CO (CH2) nHet, N [(CH2) nNR2] CO (CH2) nNRHet; R2, R3 denotes H, A, Hal , OA, O; Y denotes H, A, Hal, O; A denotes alkyl or cycloalkyl, where one or more atoms d and H can be replaced with Hal; Hal denotes F, Cl, Br or I; R denotes H or A, in the case of R geminal groups together also - (CH2) 5-, - (CH2) 4- or - (CH2) nX- (CH2) n, or - (CH2) nZ- (CH2) n; X denotes O, S or NR1; Q denotes CH2-NH-A, CH2-NH-C (O) R1, CH2-NH-SO2R1; Z denotes CH2, X, CHCONH2, CH (CH2) nNR1COOR1, CHNR1COOR1, NCHO, CHCON (R1) 2, CH (CH2) nCOOR1, NCOOR1, CH (CH2) nOH, N (CH2) nOH, CHNH2, CH (CH2) nNR12, CH (CH2) nNR12, C (OH) R1, CHNCOR1, NCOR1, N (CH2) nAR, N (CH2) nHet, CHR1, NR1, CH (CH2) nAr, CH (CH2) nHet, CH (CH2) nR1, N (CH2) nCOOR1, CH (CH2) nX (CH2) nAr, CH (CH2) nX (CH2) nHet, N (CH2) nCON (R1) 2, NSO2R1, CHSO2N (R1) 2, XCONR (CH2) nN (R1) 2, NCO (CH2) nAr, NCO (CH2) nXAr, NSO2 (CH2) nAr, NCO (CH2) nAr, NCO (CH2) nNR1aryl, NCO (CH2) nHet, NCO (CH2) nXHet, NSO2 ( CH2) nHet, NCO (CH2) nNR1Het, N (CH2) nNR2CH, CHO (CH2) nN (R1) 2, CHX (CH2) nN (R1) 2, NCO (CH2) nNR2; R6 denotes Ar or Het unsubstituted or substituted in at least one position with Hal, NO2, CN, O, A, - (CY2) nO, -OCOR, - (CY2) n-CO2R, - (CY2) n- CN, -NCOR, -COR or - (CY2) n-NR2 or with aryl or Het which can also be substituted with Hal, NO2, CN, A, O, OCOR, COR, NR2, CF3, OCF3, OCH (CF3) 2, R7 denotes (C = O) -R, (C = O) -NR2, (C = O) -O, H or A; Ar denotes a monocyclic or bicyclic, saturated, unsaturated or aromatic carbocyclic ring with between 6 and 14 carbon atoms that may not be substituted be substituted in at least one position with Hal, NO2, CN, O, A, - (CY2) nO , -OCOR, - (CY2) n-CO2R, - (CY2) n-CN, -NCOR, -COR or - (CY2) n-NR2 or by Hal, NO2, CN, A, O, OCOR, COR, NR2 , CF3, OCF3, OCH (CF3) 2; Het denotes a monocyclic or bicyclic, saturated, unsaturated or aromatic heterocyclic ring with between 1 and 4 atoms of N, O and / or S that may not be substituted or substituted in at least one position with Hal, NO2, CN, O, A, - (CY2) nO, -OCOR, - (CY2) n-CO2R, - (CY2) n-CN, -NCOR, -COR or - (CY2) n-NR2 or by Hal, NO2, CN, A, O, OCOR, COR, NR2, CF3, OCF3, OCH (CF3) 2; n denotes 0, 1, 2, 3, 4, 5, 6 or 7; and also its derivatives, solvates, tautomers, salts and polymorphic forms acceptable for pharmaceutical use comprising; reacting an aniline A derivative and an aldehyde B with a chiral dihydropyran methylamine C derivative in the presence of a suitable solvent and a Lewis protonic acid or acid where R1 to R6 and Q are as described above. Claim 12: Process for the manufacture of enantiomerically enantiomerically pure or enantiomerically pure formula C compounds: where Q is as defined in claim 1, as well as its derivatives, solvates, tautomers, salts and polymorphic forms acceptable for pharmaceutical use characterized in that it comprises next steps: treat racemic compound C, where Q is CH2NH2 or CH2NHA, preferably CH2NHCH3 with a chiral acid compound in a polar solvent to give enantiomerically or enantiomerically pure dihydropyran methylated salts and optionally use a base to obtain the free base from dihydropyran methylamine salts |
priorityDate | 2007-12-18-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
type | http://data.epo.org/linked-data/def/patent/Publication |
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