Structure-Metabolism-Relationships in the microsomal clearance of. piperazin-1-ylpyridazines
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1 Electronic Supplementary Material (ESI) for MedChemComm. This journal is The Royal Society of Chemistry 2017 Structure-Metabolism-Relationships in the microsomal clearance of piperazin-1-ylpyridazines Sabin Llona-Minguez, a * Artin Ghassemian, a Pawel Baranczewski, b Matthieu Desroses, a Tobias Koolmeister, a Per Artursson, b Martin Scobie, a and Thomas Helleday. a* a Division of Translational Medicine and Chemical Biology, Science for Life Laboratory, Department of Medical Biochemistry and Biophysics, Karolinska Institutet, Stockholm, Sweden. b Uppsala University Drug Optimization and Pharmaceutical Profiling Platform (UDOPP), Science for Life Laboratory, Department of Pharmacy, Uppsala University, Uppsala, Sweden. Supplementary Information
2 Supplementary Figures Figure S 1 Predicted Phase I metabolism sites in 1 and 29 using Meteor Nexus Figure S 2 Predicted Phase I metabolism sites in 1 and 29 using MetaPrint2D The colour highlighting an atom indicates its normalised occurrence ratio (NOR). Colour code: Red, 0.66 <= NOR <= 1.00; Yellow, 0.33 <= NOR < 0.66; Green, 0.15 <= NOR < 0.33; White, 0.00 <= NOR < 0.15; Grey, Little/no data. A high NOR indicates a more frequently reported site of metabolism in the metabolite database Rat Phase I metabolism Human Phase I metabolism
3 Figure S 3 Predicted Phase I metabolism sites in 1 and 29 using SMARTCyp The atoms in the tables are ranked by Score, with the lowest score resulting in the lowest rank, and thus the highest probability of being a site of metabolism. Only the 3 top ranking atoms are highlighted. Standard CYP2C CYP2D6 1 29
4 Figure S 4 Predicted Phase I metabolism sites in 1 and 29 using XenoSite P450 Metabolism 1.0. The atomic colour highlight indicates its probability of metabolism, see colour scale bar. 1 CYP1A2 CYP1A6 CYP1B6 CYP2C8 CYP2C9 CYP2C19 CYP2D6 CYP3A4 CYP1E1 HLM 29 CYP1A2 CYP1A6 CYP1B6 CYP2C8 CYP2C9 CYP2C19 CYP2D6 CYP3A4 CYP1E1 HLM
5 Figure S 5 Observed metabolites of 15 in mouse liver microsomes MLM (%), 30 min incubation MLM (%), 60 min incubation M M M3 3 5 M M5 2 2 Figure S 6 Observed metabolites of 16 in mouse liver microsomes MLM (%), 30 min incubation MLM (%), 60 min incubation M M M3 2 8 M4 6 8 M5 1 2
6 Figure S 7 2D correlation plots: (a) MLM E vs. clogp, (b) MLM E vs. PSA Figure S 8 Observed metabolites of 24 in mouse liver microsomes MLM (%), 30 min incubation MLM (%), 60 min incubation M M2 4 9 M M4 3 5
7 Compound characterisation 9 Chemical name N-(Thiazol-5-ylmethyl)-6-(4-(o- tolylsulfonyl)piperazin-1-yl)pyridazine-3- carboxamide 1 H NMR Yield 1 H NMR (400 MHz, CDCl 3 ) δ = 8.26 (t, J = 6.1 Hz, 1 H), 8.04 (d, J = 9.6 Hz, 1 H), (m, 1 H), 7.85 (br. s., 1 H), (m, 1 H), (m, 2 H), (m, 1H), 6.97 (d, J = 9.6 Hz, 1 H), 4.88 (d, J = 6.1 Hz, 2 H), (m, 4 H), (m, 4 H), 2.66 (s, 3 H); LC-MS (ESI+) m/z = 459 [M+H]+. 11% Synthetic Remarks B. Purified by 10 N-Benzyl-6-(4-((2- chlorophenyl)sulfonyl)piperazin-1- yl)pyridazine-3-carboxamide 1 H NMR (400 MHz, CDCl 3 ) δ = 8.20 (t, J = 6.0 Hz, 1 H), (m, 2 H), (m, 2 H), (m, 1 H), (m, 5 H), 6.99 (d, J = 9.3 Hz, 1 H), 4.68 (d, J = 6.0 Hz, 2 H), (m, 4 H), (m, 4 H); LC-MS (ESI+) m/z = 472 [M+H]+. 61% FCC (5-80% 11 N-Benzyl-6-(4-((2,3- dichlorophenyl)sulfonyl)piperazin-1- yl)pyridazine-3-carboxamide 1 H NMR (400MHz, CDCl 3 ) δ = 8.19 (t, J = 5.9 Hz, 1 H), 8.06 (d, J = 9.5 Hz, 1 H), 8.03 (dd, J = 1.5, 8.0 Hz, 1 H), 7.69 (dd, J = 1.8, 8.0 Hz, 1 H), (m, 1 H), (m, 5 H), 6.99 (d, J = 9.5 Hz, 1 H), 4.66 (d, J = 5.8 Hz, 2 H), 3.85 (d, J = 3.3 Hz, 4 H), (m, 4 H); LC-MS (ESI+) m/z = 506 [M+H]+. 68% FCC (20-100% pentane). 12 N-Benzyl-6-(4-((2,3- dichlorophenyl)sulfonyl)piperidin-1- yl)pyridazine-3-carboxamide 1 H NMR (400MHz, DMSO-d 6 ) δ = 9.39 (t, J = 6.5 Hz, 1 H), 8.08 (dd, J = 1.6, 7.9 Hz, 1 H), (m, 1 H), 7.85 (d, J = 9.8 Hz, 1 H), 7.66 (t, 1 H), 7.39 (d, J = 9.5 Hz, 1 H), (m, 3 H), (m, J = 7.9 Hz, 1 H), (m, 2 H), 4.48 (d, J = 6.3 Hz, 2 H), (m, 1 H), (m, 2 H), (m, 2 H), 1.64 (app qd, J = 4.3, 12.4 Hz, 2 H); LC-MS (ESI+) m/z = 505 [M+H]+. 63% C. Purified by HPLC basic 13 6-(4-((4-Fluoro-2- methylphenyl)sulfonyl)piperazin-1-yl)-n- (4-1 H NMR (400 MHz, CDCl 3 ) δ = (m, 1 H), (m, 1 H), (m, 1 H), (m, 2 H), (m, 5 H), 4.63 (d, J = 6.1 Hz, 2 H), (m, 4 H), (m, 4 H), 2.65 (s, 3 H); LC- MS (ESI+) m/z = 488 [M+H]+. 64% FCC (40-95% 14 6-(4-((5-Fluoro-2- methylphenyl)sulfonyl)piperazin-1-yl)-n- (4-1 H NMR (400 MHz, CDCl 3 ) δ = (m, 1 H), 8.08 (d, J = 9.3 Hz, 1 H), 7.66 (dd, J = 8.6, 2.8 Hz, 1 H), (m, 3 H), (m, 1 H), (m, 3 H), 4.64 (d, J = 6.1 Hz, 2 H), (m, 4 H), (m, 4 H), 2.63 (s, 3 H); LC-MS (ESI+) m/z = 488 [M+H]+. 94% FCC (40-100% petroleum ether). 15 N-(4-Fluorobenzyl)-6-(4-((2- (trifluoromethyl)phenyl)sulfonyl)piperazin- 1-yl)pyridazine-3-carboxamide 1 H NMR (400 MHz, CDCl 3 ) δ = 8.18 (s, 2 H), 8.06 (d, J = 9.3 Hz, 1 H), (m, 1 H), (m, 2 H), (m, 2 H), (m, 3 H), 4.63 (d, J = 6.1 Hz, 2 H), (m, 4 H), (m, 4 H); LC- MS (ESI+) m/z = 524 [M+H]+. 58% FCC (40-95% 16 6-(4-((4-Fluoro-2- (trifluoromethyl)phenyl)sulfonyl)piperazin- 1-yl)-N-(4-fluorobenzyl)pyridazine-3- carboxamide 1 H NMR (400 MHz, CDCl 3 ) δ = 8.20 (s, 2 H), 8.07 (d, J = 9.3 Hz, 1 H), (m, 1 H), (m, 1 H), (m, 2 H), (m, 3 H), 4.63 (d, J = 6.1 Hz, 2 H), (m, 4 H), (m, 4 H); LC- MS (ESI+) m/z = 542 [M+H]+. 55% FCC (40-95% 17 4-Fluorobenzyl 5-(4-(o- tolylsulfonyl)piperazin-1-yl)pyrazine-2- carboxamide 1 H NMR (400 MHz, CDCl 3 ) δ = 8.87 (d, J = 1.5 Hz, 1 H), (m, 2 H), 7.79 (t, J = 6.1 Hz, 1 H), (m, 1 H), (m, 4 H), (m, 2 H), 4.60 (d, J = 6.1 Hz, 2 H), (m, 4 H), (m, 4 H), 2.66 (s, 3 H); LC-MS (ESI+) m/z = 470 [M+H]+. 46% B. Purified by ph 18 N-(4-Fluorobenzyl)-6-(1-(o-tolylsulfonyl)- 1,2,3,6-tetrahydropyridin-4-yl)pyridazine- 3-carboxamide 1 H NMR (400 MHz, CDCl 3 ) δ = 8.48 (t, J = 6.1 Hz, 1 H), 8.27 (d, J = 8.8 Hz, 1 H), 7.97 (dd, J = 1.3, 7.8 Hz, 1 H), 7.75 (d, J = 8.8 Hz, 1 H), (m, 1 H), (m, 4 H), (m, 2 H), m, 1 H), 4.66 (d, J = 6.1 Hz, 2 H), 4.03 (app q, J = 2.7 Hz, 2 H), 3.53 (app t, J = 5.7 Hz, 2 H), (m, 2 H), 2.64 (s, 3 H); LC-MS (ESI+) m/z = 467 [M+H]+. 86% FCC (20-80%
8 19 N-(4-Fluorobenzyl)-6-(6-(o-tolylsulfonyl)- 2,6-diazaspiro[3.3]heptan-2-yl)pyridazine- 3-carboxamide 1 H NMR (400 MHz, CDCl 3 ) δ = 8.18 (t, J = 6.2 Hz, 1 H), 8.11 (d, J = 9.3 Hz, 1 H), 7.95 (td, J = 0.9, 7.6 Hz, 1 H), (m, 1 H), (m, 4 H), (m, 2 H), 6.71 (d, J = 9.3 Hz, 1 H), 4.61 (d, J = 6.2 Hz, 2 H), 4.39 (br s, 4 H), 4.11 (br s, 4 H), (m, 3 H); LC- MS (ESI+) m/z = 482 [M+H]+. 25% ph 21 N-(4-Fluorobenzyl)-6-(4-((2-methyl-6- (trifluoromethyl)pyridin-3- yl)sulfonyl)piperazin-1-yl)pyridazine-3- carboxamide 1 H NMR (400 MHz, CDCl 3 ) δ = 8.39 (d, J = 8.1 Hz, 1 H), 8.08 (d, J = 9.6 Hz, 1 H), 7.69 (d, J = 8.1 Hz, 1 H), (m, 2 H), (m, 3 H), 4.62 (s, 2 H), (m, 4 H), (m, 4 H), 2.94 (s, 3 H); LC-MS (ESI+) m/z = 539 [M+H]+. 16% 22 6-(4-((2-Cyclopropylpyridin-3- yl)sulfonyl)piperazin-1-yl)-n-(4-1 H NMR (400 MHz, CDCl 3 ) δ = 8.60 (dd, J = 4.8, 1.8 Hz, 1 H), (m, 2 H), 8.06 (d, J = 9.3 Hz, 1 H), (m, 2 H), 7.18 (dd, J = 8.1, 4.8 Hz, 1 H), (m, 3 H), 4.62 (d, J = 6.1 Hz, 2 H), (m, 4 H), (m, 4 H), (m, 1 H), (m, 2 H), (m, 2 H); LC-MS (ESI+) m/z = 497 [M+H]+. 18% 23 6-(4-((2-Cyanopyridin-3- yl)sulfonyl)piperazin-1-yl)-n-(4-1 H NMR (400 MHz, CDCl 3 ) δ = 8.90 (dd, J = 1.5, 4.8 Hz, 1 H), 8.37 (dd, J = 1.5, 8.1 Hz, 1 H), 8.19 (t, J = 5.8 Hz, 1 H), 8.07 (d, J = 9.3 Hz, 1 H), 7.72 (dd, J = 4.7, 8.2 Hz, 1 H), (m, 2 H), (m, 3 H), 4.62 (d, J = 5.8 Hz, 2 H), (m, 4 H), (m, 4 H); LC-MS (ESI+) m/z = 482 [M+H]+. 56% 24 3-(4-((2-Cyanopyridin-3- yl)sulfonyl)piperazin-1-yl)-6-((4- fluorobenzyl)carbamoyl)pyridazine 1- oxide 1 H NMR (400 MHz, CDCl 3 ) δ = (t, J = 6.0 Hz, 1 H), 8.92 (dd, J = 1.8, 4.8 Hz, 1 H), 8.43 (d, J = 9.3 Hz, 1 H), 8.38 (dd, J = 1.6, 8.2 Hz, 1 H), 7.74 (dd, J = 4.8, 8.2 Hz, 1 H), (m, 2 H), (m, 2 H), 6.70 (d, J = 9.3 Hz, 1 H), 4.62 (d, J = 6.0 Hz, 2 H), (m, 4 H), (m, 4 H); LC-MS (ESI+) m/z = 498 [M+H]+. 75% Prepared from 23. Purified by 25 6-(4-((2-Aminopyridin-3- yl)sulfonyl)piperazin-1-yl)-n-(4-1 H NMR (400 MHz, MeOH- d4 ) δ = 8.58 (d, J = 4.3 Hz, 1 H), (m, 1 H), 7.94 (d, J = 9.3 Hz, 1 H), (m, 1 H), (m, 2 H), (m, 1 H), 6.93 (t, J = 8.7 Hz, 2 H), 4.52 (s, 2 H), (m, 4 H), (m, 4 H); LC-MS (ESI+) m/z = 472 [M+H]+. 73% 26 N-(4-Fluorobenzyl)-6-(4-((2- morpholinopyridin-3-yl)sulfonyl)piperazin- 1-yl)pyridazine-3-carboxamide 2,2,2- trifluoroacetate 1 H NMR (400 MHz, CDCl 3 ) δ = 8.52 (dd, J = 4.8, 1.8 Hz, 1 H), 8.25 (dd, J = 7.8, 2.0 Hz, 2 H), 8.17 (d, J = 9.6 Hz, 1 H), (m, 2 H), 7.19 (dd, J = 8.0, 4.9 Hz, 1 H), 7.13 (d, J = 9.6 Hz, 1 H), (m, 2 H), 4.64 (d, J = 6.1 Hz, 2 H), (m, 4 H), (m, 4 H), 3.37 (m, 8 H); LC-MS (ESI+) m/z = 542 [M+H]+. 11% 27 N-(4-Fluorobenzyl)-6-(4-((2- hydroxypyridin-3-yl)sulfonyl)piperazin-1- yl)pyridazine-3-carboxamide 1 H NMR (400 MHz, CDCl 3 ) δ = 8.32 (dd, J = 7.3, 2.0 Hz, 1 H), 8.24 (t, J = 5.9 Hz, 1 H), 8.10 (d, J = 9.6 Hz, 1 H), (m, 1 H), (m, 2 H), (m, 3 H), 6.55 (t, J = 6.9 Hz, 1 H), 4.62 (d, J = 6.1 Hz, 2 H), (m, 4 H), (m, 4 H); LC-MS (ESI+) m/z = 473 [M+H]+. 16% HPLC basic 28 6-(4-((2-Chloropyridin-3- yl)sulfonyl)piperazin-1-yl)-n-(4-1 H NMR (400 MHz, CDCl 3 ) δ = 8.59 (dd, J = 4.8, 1.8 Hz, 1 H), 8.43 (dd, J = 7.8, 2.0 Hz, 1 H), 8.19 (br. s, 1 H), 8.08 (d, J = 9.3 Hz, 1 H), 7.45 (dd, J = 7.8, 4.8 Hz, 1 H), (m, 2 H), (m, 3 H), 4.63 (d, J = 6.1 Hz, 2 H), (m, 4 H), (m, 4 H); LC- MS (ESI+) m/z = 491 [M+H]+. 29% 29 6-(6-((2-Chloropyridin-3-yl)sulfonyl)-2,6- diazaspiro[3.3]heptan-2-yl)-n-(4-1 H NMR (400 MHz, CDCl 3 ) δ = 8.60 (dd, J = 1.7, 4.9 Hz, 1H), 8.49 (dd, J = 1.7, 7.6 Hz, 1H), 8.18 (t, J = 6.2 Hz, 1 H), 8.12 (d, J = 9.3 Hz, 1 H), 7.41 (dd, J = 4.9, 7.6 Hz, 1H), (m, 2 H), (m, 2 H), 6.71 (d, J = 9.3 Hz, 1 H), 4.61 (d, J = 6.2 Hz, 2 H), 4.38 (br s, 4 H), 4.11 (br s, 4 H), (m, 3 H); LC-MS (ESI+) m/z = 503 [M+H]+. 15% ph
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