Prmt5 inhibitors
A C2H5, halogen technology for the genetic persistence of sickle cell and fetal hemoglobin mutations, PRMT5 inhibitors, the treatment of cancer, the preparation of compounds of formula I, which can solve elusive problems
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[0350] Some specific examples of tyrosine kinase inhibitors: include N-(trifluoromethylphenyl)-5-methylisoxazole-4-carboxamide, 3-[(2,4-dimethylpyrrole-5 -yl)methylene)indol-2-one, 17-(allylamino)-17-desmethoxygeldanamycin, 4-(3-chloro-4-fluorophenylamino)- 7-Methoxy-6-[3-(4-morpholinyl)propoxy]quinazoline, N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy base)-4-quinazolinamine, BIBX1382, 2,3,9,10,11,12-hexahydro-10-(hydroxymethyl)-10-hydroxy-9-methyl-9,12-epoxy -1H-Diindolo[1,2,3-fg:3',2',1'-kl]pyrrolo[3,4-i][1,6]benzodiazon-1-one, SH268 , genistein, STI571, CEP2563, 4-(3-chlorophenylamino)-5,6-dimethyl-7H-pyrrolo[2,3-d]pyrimidine methanesulfonate, 4-(3- Bromo-4-hydroxyphenyl)amino-6,7-dimethoxyquinazoline, 4-(4'-hydroxyphenyl)amino-6,7-dimethoxyquinazoline, SU6668, STI571A, N-4-Chlorophenyl-4-(4-pyridylmethyl)-1-phthalazinamine and EMD121974.
[0351] Combinations with compounds other than anticancer compounds are also included in this method. For example, combinations of c...
Embodiment 1
[0816] (1R, 2S, 3R, 5R)-5-(((2-amino-3-bromoquinolin-7-yl)oxy)methyl)-3-(4-chloro-7H-pyrrolo [2,3-d]pyrimidin-7-yl)-1-methylcyclopentane-1,2-diol
[0817]
[0818] step 1: ((3aR, 4R, 6R, 6aS)-6-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2,3a-trimethyltetrahydro-3aH -Cyclopenta[d][1,3]dioxol-4-yl)methanol (1.2g, 3.6mmol), 2-amino-3-bromoquinolin-7-ol (0.934 g, 3.91 mmol) and triphenylphosphine (1.86 g, 7.10 mmol) were coevaporated with dry toluene (three times, 10 mL each) and then redissolved in anhydrous THF (20 mL). The reaction mixture was cooled to 0°C, and (E)-diisopropyldiazene-1,2-dicarboxylate (1.44 g, 7.10 mmol) was added dropwise at 0°C. The mixture was naturally warmed to room temperature, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0-10% MeOH in DCM). Fractions containing the desired product were combined and...
Embodiment 2
[0821] (1R,2S,3R,5R)-5-(((2-amino-3-bromoquinolin-7-yl)oxy)methyl)-3-(4-amino-7H-pyrrole And[2,3-d]pyrimidin-7-yl)-1-methylcyclopentane-1,2-diol
[0822]
[0823] To a sealed tube (10 mL) was added (1R,2S,3R,5R)-5-(((2-amino-3-bromoquinolin-7-yl)oxy)methyl)-3-( 4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-1-methylcyclopentane-1,2-diol (350mg, 0.675mmol), 1,4-dioxane (3mL) and NH 3 ·H 2 O (5 mL; 25%-28% w / w). The reaction mixture was sealed tightly and then stirred at 90°C for 16 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified by reverse phase HPLC (0-45% acetonitrile / water) to give (1R,2S,3R,5R)-5-(((2-amino-3-bromoquinolin-7-yl)oxy) Methyl)-3-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-1-methylcyclopentane-1,2-diol. MS 499,501 (M+1,M+3). 1 H NMR (400MHz, DMSO-d 6 )δ8.28(s,1H),8.02(s,1H),7.58(d,J=8.7Hz,1H),7.30(d,J=3.6Hz,1H),6.96–6.89(m,4H), 6.57–6.53(m,3H),4.97–4.91(m,2H),4.41(s,1H),4.19–4.10(m,3H),2.45–2.37(m,2H),1.72–...
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