http://rdf.ncbi.nlm.nih.gov/pubchem/patent/ES-2837034-T3

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filingDate 2014-03-14-04:00^^<http://www.w3.org/2001/XMLSchema#date>
grantDate 2021-06-29-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_0879f935a706e1195612594c734bb760
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publicationDate 2021-06-29-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber ES-2837034-T3
titleOfInvention Arginine methyltransferase inhibitors and their uses
abstract Compound of formula (I): ** (See formula) ** or a pharmaceutically acceptable salt thereof, wherein: X is N, Z is NR4, and Y is CR5, or X is NR4, Z is N, and Y is CR5, or X is CR5, Z is NR4, and Y is N, or X is CR5, Z is N, and Y is NR4, Rx is methyl, ethyl, isopropyl, hydroxyethyl, or methoxyethyl, L1 is a bond or a saturated or unsaturated unsubstituted C1-6 hydrocarbon chain, RW is optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl, with the proviso that, in case L1 is a bond, RW is not substituted aryl optionally, or optionally substituted heteroaryl, R3 is hydrogen or methyl, R4 is hydrogen or methyl, R5 is hydrogen or methyl, wherein, unless otherwise indicated, heterocyclyl or heterocyclic refers to a radical of a non-ring system. aromatic of 3 to 14 elements having ring carbon atoms and 1 to 4 ring heteroatoms, in which each heteroatom or is independently selected from nitrogen, oxygen, and sulfur, carbocyclic or carbocyclic refers to a radical of a non-aromatic cyclic hydrocarbon group having 3 to 14 ring carbon atoms and zero heteroatoms in the non-aromatic ring system, aryl refers to to a monocyclic or polycyclic aromatic ring system having 6 to 14 ring carbon atoms and zero heteroatoms provided in the aromatic ring system, and heteroaryl refers to a radical of a 4n + 2 aromatic ring system of 5 to 10 monocyclic or bicyclic elements having ring carbon atoms and 1 to 4 ring heteroatoms provided in the aromatic ring system, where each hetero atom is independently selected from nitrogen, oxygen and sulfur, alkyl refers to a radical of a straight or branched chain saturated hydrocarbon group having 1 to 20 carbon atoms, alkenyl refers to a radical of a straight chain hydrocarbon group or amified having 2 to 20 carbon atoms and one or more carbon-carbon double bonds, and alkynyl refers to a radical of a straight or branched chain hydrocarbon group having 2 to 20 carbon atoms and one or more triple carbon bonds -carbon, are optional substituents on a carbon atom, halogen, -CN, -NO2, -N3, -SO2H, -SO3H, -OH, -ORaa, -ON (Rbb) 2, -N (Rbb) 2, -N (Rbb) 3 + X-, -N (ORcc) Rbb, -SH, -SRaa, -SSRcc, -C (= O) Raa, -CO2H, -CHO, -C (ORcc) 2, - CO2Raa, -OC (= O) Raa, -OCO2Raa, -C (= O) N (Rbb) 2, - OC (= O) N (Rbb) 2, -NRbbC (= O) Raa, -NRbbCO2Raa, - NRbbC (= O) N (Rbb) 2, -C (= NRbb) Raa, - C (= NRbb) ORaa, -OC (= NRbb) Raa, -OC (= NRbb) ORaa, -C (= NRbb) N (Rbb) 2, -OC (= NRbb) N (Rbb) 2, -NRbbC (= NRbb) N (Rbb) 2, -C (= O) NRbbSO2Raa, -NRbbSO2Raa, -SO2N (Rbb) 2, -SO2Raa, - SO2ORaa, -OSO2Raa , -S (= O) Raa, -OS (= O) Raa, -Si (Raa) 3, -OSi (Raa) 3 -C (= S) N (Rbb) 2, -C (= O) SRaa, - C (= S) SRaa, -SC (= S) SRaa, -SC (= O) SRaa, -OC (= O) SRaa, -SC (= O) ORaa, - SC (= O) Raa, -P (= O) 2Raa, - OP (= O) 2Raa, -P (= O) (Raa) 2, -OP (= O) (Raa) 2, -OP (= O) (ORcc) 2, -P ( = O) 2N (Rbb) 2, -OP (= O) 2N (Rbb) 2, - P (= O) (NRbb) 2, -OP (= O) (NRbb) 2, -NRbbP (= O) ( ORcc) 2, -NRbbP (= O) (NRbb) 2, -P (Rcc) 2, -P (Rcc) 3, -OP (Rcc) 2, - OP (Rcc) 3, -B (Raa) 2, -B (ORcc) 2, -BRaa (ORcc), C1-10 alkyl, C1-10 perhaloalkyl, C2-10 alkenyl, C2-10 alkynyl, C3-10 carbocyclyl, 3-14 membered heterocyclyl, C6-14 aryl and 5- to 14-membered heteroaryl, wherein each alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, aryl, and heteroaryl is independently substituted with 0, 1, 2, 3, 4, or 5 Rdd groups, or two geminal hydrogens on one atom of carbon are substituted with the group = O, = S, = NN (Rbb) 2, = NNRbbC (= O) Raa, = NNRbbC (= O) ORaa, = NNRbbS (= O) 2Raa, = NRbb, or = NORcc, each occurrence of Raa is independently selected from C1-10 alkyl, C1-10 perhaloalkyl, C2-10 alkenyl, C2-10 alkynyl, C3-10 carbocyclyl, 3-14 membered heterocyclyl, C6-14 aryl, and 5-heteroaryl to 14 elements, or two Raa groups join to form a 3- to 14-membered heterocyclyl or a heteroaryl ring of 5 to 14 elements, wherein each alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, aryl, and heteroaryl is independently substituted with 0, 1, 2, 3, 4, or 5 Rdd groups, each occurrence of Rbb is independently selected from hydrogen, -OH, -ORaa, - N (Rcc) 2, -CN, -C (= O) Raa, -C (= O) N (Rcc) 2, -CO2Raa, -SO2Raa, -C (= NRcc) ORaa, - C (= NRcc) N (Rcc) 2, -SO2N (Rcc) 2, -SO2Rcc, -SO2ORcc, - SORaa, -C (= S) N (Rcc) 2, -C (= O) SRcc, - C (= S) SRcc, -P (= O) 2Raa, -P (= O) (Raa) 2, -P (= O) 2N (Rcc) 2, -P (= O) (NRcc) 2, C1 alkyl -10, C1-10 perhaloalkyl, C2-10 alkenyl, C2-10 alkynyl, C3-10 carbocyclyl, 3-14 membered heterocyclyl, C6-14 aryl and 5-14 membered heteroaryl, or two Rbb groups join to form a 3-14 membered heterocyclyl or a 5-14 membered heteroaryl ring, wherein each alkyl, alkenyl, carbocyclyl, heterocyclyl, aryl, and heteroaryl is independently substituted with 0, 1, 2, 3, 4, or 5 Rdd groups, each case Rcc is independently selected from hydrogen, alkyl C1-10, C1-10 perhaloalkyl, C2-10 alkenyl, C2-10 alkynyl, C3-10 carbocyclyl, 3-14 membered heterocyclyl, C6-14 aryl and 5-14 membered heteroaryl, or two Rcc groups join to form a 3- to 14-membered heterocyclyl or a 5- to 14-membered heteroaryl ring, wherein each alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, aryl, and heteroaryl is independently substituted with 0, 1, 2, 3, 4, or 5 groups Rdd, each occurrence of Rdd is independently selected from halogen, -CN, -NO2, -N3, - SO2H, -SO3H, -OH, -ORee, -ON (Rff) 2, -N (Rff) 2, - N (Rff) 3 + X-, -N (ORee) Rff, -SH, -SRee, - SSRee, -C (= O) Ree, -CO2H, -CO2Ree, - OC (= O) Ree, -OCO2Ree, -C (= O) N (Rff) 2, - OC (= O) N (Rff) 2, -NRffC (= O) Ree, -NRffCO2Ree, -NRffC (= O) N (Rff) 2, - C ( = NRff) ORee, -OC (= NRff) Ree, -OC (= NRff) ORee, -C (= NRff) N (Rff) 2, -OC (= NRff) N (Rff) 2, - NRffC (= NRff ) N (Rff) 2, - NRffSO2Ree, -SO2N (Rff) 2, -SO2Ree, -SO2ORee, -OSO2Ree, -S (= O) Ree, -Si (Ree) 3, -OSi (Ree) 3, -C (= S) N (Rff) 2, - C (= O) SRee, -C (= S) SRee, -SC (= S) SRee, -P ( = O) 2Ree, - P (= O) (Ree) 2, -OP (= O) (Ree) 2, -OP (= O) (ORee) 2, C1-6 alkyl, C1-6 perhaloalkyl, C2 alkenyl -6, C2-6 alkynyl, C3-10 carbocyclyl, 3-10 membered heterocyclyl, C6-10 aryl, 5-10 membered heteroaryl, wherein each alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, aryl, and heteroaryl are independently substituted with 0, 1, 2, 3, 4 or 5 Rgg groups, or two geminal Rdd substituents can join together to form = O or = S, each occurrence of Ree is independently selected from C1-6 alkyl, C1- perhaloalkyl 6, C2-6 alkenyl, C2-6 alkynyl, C3-10 carbocyclyl, C6-10 aryl, 3-10 membered heterocyclyl, and 3-10 membered heteroaryl, wherein each alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, aryl and heteroaryl are independently substituted with 0, 1, 2, 3, 4 or 5 Rgg groups, each occurrence of Rff is independently selected from hydrogen, C1-6 alkyl, C1-6 perhaloalkyl, C2-6 alkenyl, C2 alkynyl -6, C3-10 carbocyclyl, heterocyc 3-10 membered lyl, C6-10 aryl and 5-10 membered heteroaryl, or two Rff groups join together to form a 3-14 membered heterocyclyl or 5-14 membered heteroaryl ring, wherein each alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, aryl, and heteroaryl are independently substituted with 0, 1, 2, 3, 4, or 5 Rgg groups, and each occurrence of Rgg is independently halogen, -CN, -NO2, -N3, - SO2H, -SO3H, - OH, -O-C1-6 alkyl, -ON (C1-6 alkyl) 2, -N (C1-6 alkyl) 2, -N (C1-6 alkyl) 3 + X-, - NH (C1-6 alkyl) 2 + X-, -NH2 (C1-6 alkyl) + X-, - NH3 + X-, -N (O-C1-6 alkyl) (C1-6 alkyl), -N ( OH) (C1-6 alkyl), -NH (OH), -SH, -S-C1-6 alkyl, -SS (C1-6 alkyl), -C (= O) (C1-6 alkyl), -CO2H , -CO2 (C1-6 alkyl), -OC (= O) (C1-6 alkyl), -OCO2 (C1-6 alkyl), - C (= O) NH2, -C (= O) N (C1 alkyl) -6) 2, -OC (= O) NH (C1-6 alkyl), -NHC (= O) (C1-6 alkyl), -N (C1-6 alkyl) C (= O) (C1-6 alkyl ), - NHCO2 (C1-6 alkyl), -NHC (= O) N (C1-6 alkyl) 2, -NHC (= O) NH (C1-6 alkyl), - NHC (= O) NH2, -C (= NH) O (alk C1-6 uyl), -OC (= NH) (C1-6 alkyl), -OC (= NH) O-C1-6 alkyl, -C (= NH) N (C1-6 alkyl) 2, -C ( = NH) NH (C1-6 alkyl), -C (= NH) NH2, -OC (= NH) N (C1-6 alkyl) 2, - OC (NH) NH (C1-6 alkyl), - OC ( NH) NH2, -NHC (NH) N (C1-6 alkyl) 2, -NHC (= NH) NH2, - NHSO2 (C1-6 alkyl), -SO2N (C1-6 alkyl) 2, - SO2NH (C1 alkyl -6), -SO2NH2, -SO2-C1-6 alkyl, - SO2O-C1-6 alkyl, -OSO2-C1-6 alkyl, -SO-C1-6 alkyl, -Si (C1-6 alkyl) 3, - OSi (C1-6 alkyl) 3 - C (= S) N (C1-6 alkyl) 2, C (= S) NH (C1-6 alkyl), C (= S) NH2, - C (= O) S (C1-6 alkyl), -C (= S) S-C1-6 alkyl, -SC (= S) S-C1-6 alkyl, -P (= O) 2 (C1-6 alkyl), -P ( = O) (C1-6 alkyl) 2, -OP (= O) (C1-6 alkyl) 2, - OP (= O) (O-C1-6 alkyl) 2, C1-6 alkyl, C1-6 perhaloalkyl , C2-6 alkenyl, C2-6 alkynyl, C3-10 carbocyclyl, C6-10 aryl, 3- to 10-membered heterocyclyl, 5 to 10-membered heteroaryl, or two geminal Rgg substituents can join to form = O or = S, where X- is a counter ion, and are substituents on a nitrogen atom, hydrogen, -OH, -ORaa, -N (Rcc) 2, -CN, -C ( = O) Raa, - C (= O) N (Rcc) 2, -CO2Raa, -SO2Raa, -C (= NRbb) Raa, -C (= NRcc) ORaa, - C (= NRcc) N (Rcc) 2 , -SO2N (Rcc) 2, -SO2Rcc, -SO2ORcc, -SORaa, -C (= S) N (Rcc) 2, -C (= O) SRcc, - C (= S) SRcc, -P (= O ) 2Raa, -P (= O) (Raa) 2, -P (= O) 2N (Rcc) 2, - P (= O) (NRcc) 2, C1-10 alkyl, C1-10 perhaloalkyl, C2- alkenyl 10, C2-10 alkynyl, C3-10 carbocyclyl, 3-14 membered heterocyclyl, C6-14 aryl and 5-14 membered heteroaryl, or two Rcc groups attached to a nitrogen atom join to form a 3-14 heterocyclyl elements or a 5- to 14-membered heteroaryl ring, wherein each alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, aryl, and heteroaryl is independently substituted with 0, 1, 2, 3, 4, or 5 Rdd groups, and wherein Raa, Rbb, Rcc and Rdd are as defined above.
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Total number of triples: 1242.