http://rdf.ncbi.nlm.nih.gov/pubchem/patent/ES-2727869-T3

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filingDate 2014-03-13-04:00^^<http://www.w3.org/2001/XMLSchema#date>
grantDate 2019-10-21-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_b77710c90c1881cc93973d7c2c476cc6
http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_89061b857e93adf43ae6a24419d4f658
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publicationDate 2019-10-21-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber ES-2727869-T3
titleOfInvention Method for preparing glucosylceramide synthase inhibitors
abstract A method for preparing a compound of the formula, ** Formula ** in which: n is 1, 2 or 3; m is 1; t is 0, 1 or 2; y is 1 or 2; z is 0, 1 or 2; E is O; X1 is CR1; X2 is O; X3 is -NH; X4 is CR4R5, CH2 CR4R5 or CH2-(C1-C6) alkyl -CR4R5; X5 is a direct link, O, S, SO2, CR4R5; (C1-C6) alkyl, (C1-C6) alkyloxy, (C1-C6) alkenyl, (C1-C6) alkenyloxy; R1 is H, CN, (C1-C6) alkylcarbonyl, or (C1-C6) alkyl; R4 and R5 are independently selected from H, (C1-C6) alkyl, or, taken together with the carbon to which they are attached, form a cycloalkyl spiro ring (C3-C10) or a cycloalkoxy spiro ring (C3-C10) ; R6 is -H, halogen, -CN, (C6-C12) aryl, (C6-C12) aryloxy, (C1-C6) alkyloxy; (C1-C6) alkyl optionally substituted with one to four halo or (C1-C6) alkyl; A1 is alkynyl (C2-C6); cycloalkyl (C3-C10), aryl (C6-C12), heteroaryl (C2-C9), heterocycloalkyl (C2-C9) or benzoheterocycloalkyl (C2-C9) optionally substituted with one or more substituents selected from the group consisting of halo, alkyl (C1-C6) optionally substituted with one to three halo; (C1-C6) alkenyl, amino, (C1-C6) alkylamino, (C1-C6) dialkylamino, (C1-C6) alkoxy, nitro, CN, -OH, (C1-C6) alkyloxy optionally substituted with one to three halo ; (C1-C6) alkoxycarbonyl, and (C1-C6) alkylcarbonyl; A2 is H, cycloalkyl (C3-C10), aryl (C6-C12), heteroaryl (C2-C9), heterocycloalkyl (C2-C9) or benzoheterocycloalkyl (C2-C9) optionally substituted with one or more substituents selected from the group consisting in halo, (C1-C6) alkyl optionally substituted with one to three halo; (C1-C6) alkylenyl, amino, (C1-C6) alkylamino, (C1-C6) dialkylamino, (C1-C6) alkoxy, O (C3-C6 cycloalkyl), cycloalkoxy (C3-C6), nitro, CN, OH, (C1-C6) alkyloxy optionally substituted with one to three halo; (C3-C6) cycloalkyl, (C1-C6) alkoxycarbonyl, (C1-C6) alkylcarbonyl, (C1-C6) haloalkyl; with the proviso that the sum of n + t + y + z is not greater than 6; which comprises reacting the compound of Formula II and the compound of Formula IV ** Formula ** with a compound of Formula III ** Formula ** in which n, t, y, z, X4, A1, X5 and A2 are as defined above. including the method of reacting, while heating to reflux, the compound of Formula V ** Formula ** with imidazole to form the compounds of Formula II and Formula IV ** Formula ** in which X4, A1, X5 and A2 are as defined above.
priorityDate 2013-03-15-04:00^^<http://www.w3.org/2001/XMLSchema#date>
type http://data.epo.org/linked-data/def/patent/Publication

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