NO320803B1 - Renin-inhibitorer, fremstilling av disse, fremstilling av preparater, samt anvendelse for fremstilling av medikamenter. - Google Patents

Info

Publication number

NO320803B1

NO320803B1 NO20015206A NO20015206A NO320803B1 NO 320803 B1 NO320803 B1 NO 320803B1 NO 20015206 A NO20015206 A NO 20015206A NO 20015206 A NO20015206 A NO 20015206A NO 320803 B1 NO320803 B1 NO 320803B1

Authority

NO

Norway

Prior art keywords

methoxy

ylmethoxy

propoxy

phenyl

naphthalen

Prior art date

1999-04-27

Links

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• 238000004519 manufacturing process Methods 0.000 title claims description 13
• 239000003814 drug Substances 0.000 title claims description 8
• 238000002360 preparation method Methods 0.000 title description 12
• 239000002461 renin inhibitor Substances 0.000 title description 3
• 229940086526 renin-inhibitors Drugs 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims description 136
• 238000000034 method Methods 0.000 claims description 79
• -1 4-methoxynaphthalen-2-yl Chemical group 0.000 claims description 68
• 150000003839 salts Chemical class 0.000 claims description 36
• 125000006239 protecting group Chemical group 0.000 claims description 29
• 239000001257 hydrogen Substances 0.000 claims description 22
• 229910052739 hydrogen Inorganic materials 0.000 claims description 22
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
• 150000002431 hydrogen Chemical group 0.000 claims description 13
• 229910052736 halogen Inorganic materials 0.000 claims description 12
• 150000002367 halogens Chemical class 0.000 claims description 12
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• 206010020772 Hypertension Diseases 0.000 claims description 11
• 239000000654 additive Substances 0.000 claims description 10
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 10
• 125000001424 substituent group Chemical group 0.000 claims description 10
• 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 208000010412 Glaucoma Diseases 0.000 claims description 8
• 206010019280 Heart failures Diseases 0.000 claims description 8
• 208000001647 Renal Insufficiency Diseases 0.000 claims description 8
• 201000006370 kidney failure Diseases 0.000 claims description 8
• 208000010125 myocardial infarction Diseases 0.000 claims description 8
• 208000037803 restenosis Diseases 0.000 claims description 8
• 125000003545 alkoxy group Chemical group 0.000 claims description 7
• 125000001624 naphthyl group Chemical group 0.000 claims description 7
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• NSAUOOQLSGAVDH-YYZIUVEKSA-N (2r)-1-methoxy-3-[(3s,4r,5r)-5-[(4-methoxynaphthalen-2-yl)methoxy]-4-[4-[3-[(2-methoxyphenyl)methoxy]propoxy]phenyl]piperidin-3-yl]oxypropan-2-ol Chemical compound C1=CC([C@@H]2[C@@H](OCC=3C=C4C=CC=CC4=C(OC)C=3)CNC[C@H]2OC[C@H](O)COC)=CC=C1OCCCOCC1=CC=CC=C1OC NSAUOOQLSGAVDH-YYZIUVEKSA-N 0.000 claims description 5
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
• 230000008816 organ damage Effects 0.000 claims description 5
• QRFDLBDVWFBKSU-ZYQOJWKCSA-N (2r)-1-(2-methoxyethoxy)-3-[(3s,4r,5r)-5-[(4-methoxynaphthalen-2-yl)methoxy]-4-[4-[3-[(2-methoxyphenyl)methoxy]propoxy]phenyl]piperidin-3-yl]oxypropan-2-ol Chemical compound C1=CC([C@@H]2[C@@H](OCC=3C=C4C=CC=CC4=C(OC)C=3)CNC[C@H]2OC[C@H](O)COCCOC)=CC=C1OCCCOCC1=CC=CC=C1OC QRFDLBDVWFBKSU-ZYQOJWKCSA-N 0.000 claims description 4
• HUZOCQSMPREZTO-YYZIUVEKSA-N (2r)-1-[(3s,4r,5r)-4-[4-[3-[(5-fluoro-2-methoxyphenyl)methoxy]propoxy]phenyl]-5-[(4-methoxynaphthalen-2-yl)methoxy]piperidin-3-yl]oxy-3-methoxypropan-2-ol Chemical compound C1=CC([C@@H]2[C@@H](OCC=3C=C4C=CC=CC4=C(OC)C=3)CNC[C@H]2OC[C@H](O)COC)=CC=C1OCCCOCC1=CC(F)=CC=C1OC HUZOCQSMPREZTO-YYZIUVEKSA-N 0.000 claims description 4
• LJPUCLYLJIYZOU-MWTPBHLGSA-N (2r)-1-methoxy-3-[[(3s,4r,5r)-5-[(4-methoxynaphthalen-2-yl)methoxy]-4-[4-[3-[(2-methoxyphenyl)methoxy]propoxy]phenyl]piperidin-3-yl]methoxy]propan-2-ol Chemical compound C1=CC([C@@H]2[C@@H](OCC=3C=C4C=CC=CC4=C(OC)C=3)CNC[C@H]2COC[C@H](O)COC)=CC=C1OCCCOCC1=CC=CC=C1OC LJPUCLYLJIYZOU-MWTPBHLGSA-N 0.000 claims description 4
• FHKHJCYRTIZVOS-ZLWKXDTISA-N (2r)-3-[(3s,4r,5r)-4-[4-[3-[(5-fluoro-2-methoxyphenyl)methoxy]propoxy]phenyl]-5-[(4-methoxynaphthalen-2-yl)methoxy]piperidin-3-yl]oxypropane-1,2-diol Chemical compound COC1=CC=C(F)C=C1COCCCOC1=CC=C([C@@H]2[C@H](CNC[C@H]2OC[C@H](O)CO)OCC=2C=C3C=CC=CC3=C(OC)C=2)C=C1 FHKHJCYRTIZVOS-ZLWKXDTISA-N 0.000 claims description 4
• KCJFSYIIUNAJPV-UFSQBELCSA-N (2r)-3-[(3s,4r,5r)-5-[(4-methoxynaphthalen-2-yl)methoxy]-4-[4-[3-(2-nitrophenoxy)propoxy]phenyl]piperidin-3-yl]oxypropane-1,2-diol Chemical compound C1=CC([C@H]2[C@H](OC[C@H](O)CO)CNC[C@@H]2OCC=2C=C(C3=CC=CC=C3C=2)OC)=CC=C1OCCCOC1=CC=CC=C1[N+]([O-])=O KCJFSYIIUNAJPV-UFSQBELCSA-N 0.000 claims description 4
• BPQJGSRBGBGPDT-OYSRKBQJSA-N (2r)-3-[[(3s,4r,5r)-5-[(4-methoxynaphthalen-2-yl)methoxy]-4-[4-[3-[(2-methoxyphenyl)methoxy]propoxy]phenyl]piperidin-3-yl]methoxy]propane-1,2-diol Chemical compound COC1=CC=CC=C1COCCCOC1=CC=C([C@@H]2[C@H](CNC[C@H]2COC[C@H](O)CO)OCC=2C=C3C=CC=CC3=C(OC)C=2)C=C1 BPQJGSRBGBGPDT-OYSRKBQJSA-N 0.000 claims description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
• PHEZVSMVAGZWBE-LCFCVFAESA-N [(3s,4r,5r)-5-[(4-methoxynaphthalen-2-yl)methoxy]-4-[4-[3-[(2-methoxyphenyl)methoxy]propoxy]phenyl]piperidin-3-yl]methanol Chemical compound COC1=CC=CC=C1COCCCOC1=CC=C([C@@H]2[C@H](CNC[C@H]2CO)OCC=2C=C3C=CC=CC3=C(OC)C=2)C=C1 PHEZVSMVAGZWBE-LCFCVFAESA-N 0.000 claims description 4
• 230000000996 additive effect Effects 0.000 claims description 4
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• KLWGFXVOBGPQPW-UFSQBELCSA-N (2r)-3-[(3s,4r,5r)-4-[4-[3-(2-chlorophenoxy)propoxy]phenyl]-5-[(4-methoxynaphthalen-2-yl)methoxy]piperidin-3-yl]oxypropane-1,2-diol Chemical compound C1=CC([C@H]2[C@H](OC[C@H](O)CO)CNC[C@@H]2OCC=2C=C(C3=CC=CC=C3C=2)OC)=CC=C1OCCCOC1=CC=CC=C1Cl KLWGFXVOBGPQPW-UFSQBELCSA-N 0.000 claims description 3
• 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 3
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
• 150000004292 cyclic ethers Chemical group 0.000 claims description 3
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 3
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 3
• 230000008569 process Effects 0.000 claims description 3
• HMLXZGQNBOFDAG-ZLWKXDTISA-N (2r)-1-[(3s,4r,5r)-4-[4-[3-[(3,5-difluoro-2-methoxyphenyl)methoxy]propoxy]phenyl]-5-[(4-methoxynaphthalen-2-yl)methoxy]piperidin-3-yl]oxy-3-methoxypropan-2-ol Chemical compound C1=CC([C@@H]2[C@@H](OCC=3C=C4C=CC=CC4=C(OC)C=3)CNC[C@H]2OC[C@H](O)COC)=CC=C1OCCCOCC1=CC(F)=CC(F)=C1OC HMLXZGQNBOFDAG-ZLWKXDTISA-N 0.000 claims description 2
• CKVJVDUZPDMGBS-ZLWKXDTISA-N (2r)-1-[(3s,4r,5r)-4-[4-[3-[(3-fluoro-2-methoxyphenyl)methoxy]propoxy]phenyl]-5-[(4-methoxynaphthalen-2-yl)methoxy]piperidin-3-yl]oxy-3-methoxypropan-2-ol Chemical compound C1=CC([C@@H]2[C@@H](OCC=3C=C4C=CC=CC4=C(OC)C=3)CNC[C@H]2OC[C@H](O)COC)=CC=C1OCCCOCC1=CC=CC(F)=C1OC CKVJVDUZPDMGBS-ZLWKXDTISA-N 0.000 claims description 2
• MOCAUPZPVITHLI-SFYXBDFRSA-N (2r)-1-[(3s,4r,5r)-4-[4-[3-[(4,5-difluoro-2-methoxyphenyl)methoxy]propoxy]phenyl]-5-[(4-methoxynaphthalen-2-yl)methoxy]piperidin-3-yl]oxy-3-methoxypropan-2-ol Chemical compound C1=CC([C@@H]2[C@@H](OCC=3C=C4C=CC=CC4=C(OC)C=3)CNC[C@H]2OC[C@H](O)COC)=CC=C1OCCCOCC1=CC(F)=C(F)C=C1OC MOCAUPZPVITHLI-SFYXBDFRSA-N 0.000 claims description 2
• BNAQMZRRFOMPFZ-YYZIUVEKSA-N (2r)-1-[(3s,4r,5r)-4-[4-[3-[(4-fluoro-2-methoxyphenyl)methoxy]propoxy]phenyl]-5-[(4-methoxynaphthalen-2-yl)methoxy]piperidin-3-yl]oxy-3-methoxypropan-2-ol Chemical compound C1=CC([C@@H]2[C@@H](OCC=3C=C4C=CC=CC4=C(OC)C=3)CNC[C@H]2OC[C@H](O)COC)=CC=C1OCCCOCC1=CC=C(F)C=C1OC BNAQMZRRFOMPFZ-YYZIUVEKSA-N 0.000 claims description 2
• MWUCDASIGBSILS-DRDGVYCCSA-N (2r)-1-[(3s,4r,5r)-5-[(4-methoxynaphthalen-2-yl)methoxy]-4-[4-[3-(2-nitrophenoxy)propoxy]phenyl]piperidin-3-yl]oxy-3-(1,2,4-triazol-1-yl)propan-2-ol Chemical compound C([C@@H](O)CO[C@@H]1CNC[C@@H]([C@H]1C=1C=CC(OCCCOC=2C(=CC=CC=2)[N+]([O-])=O)=CC=1)OCC=1C=C(C2=CC=CC=C2C=1)OC)N1C=NC=N1 MWUCDASIGBSILS-DRDGVYCCSA-N 0.000 claims description 2
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
• NFQLDBLVTCSTCP-WQZSUXSPSA-N 2-[3-[4-[(3s,4r,5r)-3-[(2r)-2,3-dihydroxypropoxy]-5-[(4-methoxynaphthalen-2-yl)methoxy]piperidin-4-yl]phenoxy]propoxy]benzonitrile Chemical compound C1=CC([C@H]2[C@H](OC[C@H](O)CO)CNC[C@@H]2OCC=2C=C(C3=CC=CC=C3C=2)OC)=CC=C1OCCCOC1=CC=CC=C1C#N NFQLDBLVTCSTCP-WQZSUXSPSA-N 0.000 claims description 2
• HBZWTRJPSVWVTB-ZLWKXDTISA-N 2-[3-[4-[(3s,4r,5r)-3-[(2r)-2-hydroxy-3-methoxypropoxy]-5-[(4-methoxynaphthalen-2-yl)methoxy]piperidin-4-yl]phenoxy]propoxy]benzonitrile Chemical compound C1=CC([C@@H]2[C@@H](OCC=3C=C4C=CC=CC4=C(OC)C=3)CNC[C@H]2OC[C@H](O)COC)=CC=C1OCCCOC1=CC=CC=C1C#N HBZWTRJPSVWVTB-ZLWKXDTISA-N 0.000 claims description 2
• 201000010099 disease Diseases 0.000 claims description 2
• 125000001033 ether group Chemical group 0.000 claims description 2
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
• 230000002265 prevention Effects 0.000 claims description 2
• TVQHDSNXQVZSDX-LBUYHFENSA-N (2r)-3-[[(3s,4r,5r)-5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]methoxy]propane-1,2-diol Chemical compound C1=CC([C@@H]2[C@@H](OCC=3C=C4C=CC=CC4=CC=3)CNC[C@H]2COC[C@H](O)CO)=CC=C1OCCCOCC1=CC=CC=C1 TVQHDSNXQVZSDX-LBUYHFENSA-N 0.000 claims 1
• QSSBIBVVQIXXRP-SEXBWERRSA-N (2s)-3-[[(3s,4r,5r)-4-[4-[3-[(2-methoxyphenyl)methoxy]propoxy]phenyl]-5-(naphthalen-2-ylmethoxy)piperidin-3-yl]methoxy]propane-1,2-diol Chemical compound COC1=CC=CC=C1COCCCOC1=CC=C([C@@H]2[C@H](CNC[C@H]2COC[C@@H](O)CO)OCC=2C=C3C=CC=CC3=CC=2)C=C1 QSSBIBVVQIXXRP-SEXBWERRSA-N 0.000 claims 1
• TVQHDSNXQVZSDX-IZVAWUQISA-N (2s)-3-[[(3s,4r,5r)-5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]methoxy]propane-1,2-diol Chemical compound C1=CC([C@@H]2[C@@H](OCC=3C=C4C=CC=CC4=CC=3)CNC[C@H]2COC[C@@H](O)CO)=CC=C1OCCCOCC1=CC=CC=C1 TVQHDSNXQVZSDX-IZVAWUQISA-N 0.000 claims 1
• OGRWJHGIXDLHJQ-VUVDHCLXSA-N (3s,4r,5r)-3-(imidazol-1-ylmethyl)-5-[(4-methoxynaphthalen-2-yl)methoxy]-4-[4-[3-[(2-methoxyphenyl)methoxy]propoxy]phenyl]piperidine Chemical compound COC1=CC=CC=C1COCCCOC1=CC=C([C@@H]2[C@H](CNC[C@H]2CN2C=NC=C2)OCC=2C=C3C=CC=CC3=C(OC)C=2)C=C1 OGRWJHGIXDLHJQ-VUVDHCLXSA-N 0.000 claims 1
• FBKIXNJJGZEHSJ-PZXGITDCSA-N 2-[3-[4-[(3s,4r,5r)-3-[(2r)-2-hydroxy-3-(2-methoxyethoxy)propoxy]-5-[(4-methoxynaphthalen-2-yl)methoxy]piperidin-4-yl]phenoxy]propoxy]benzonitrile Chemical compound C1=CC([C@@H]2[C@@H](OCC=3C=C4C=CC=CC4=C(OC)C=3)CNC[C@H]2OC[C@H](O)COCCOC)=CC=C1OCCCOC1=CC=CC=C1C#N FBKIXNJJGZEHSJ-PZXGITDCSA-N 0.000 claims 1
• 125000004185 ester group Chemical group 0.000 claims 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 198
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 156
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 85
• 239000000243 solution Substances 0.000 description 65
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 64
• 239000000203 mixture Substances 0.000 description 62
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
• 239000012230 colorless oil Substances 0.000 description 49
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
• 238000006243 chemical reaction Methods 0.000 description 43
• 239000011541 reaction mixture Substances 0.000 description 41
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 39
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• 239000002904 solvent Substances 0.000 description 39
• 230000002829 reductive effect Effects 0.000 description 32
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 31
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
• 239000012074 organic phase Substances 0.000 description 30
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
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• 229910002027 silica gel Inorganic materials 0.000 description 28
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
• 239000007787 solid Substances 0.000 description 25
• 238000005804 alkylation reaction Methods 0.000 description 23
• 239000002585 base Substances 0.000 description 23
• 230000029936 alkylation Effects 0.000 description 22
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• 229910000041 hydrogen chloride Inorganic materials 0.000 description 22
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 21
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• 238000003776 cleavage reaction Methods 0.000 description 21
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• DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 20
• 238000003756 stirring Methods 0.000 description 19
• 239000012043 crude product Substances 0.000 description 18
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• 235000017557 sodium bicarbonate Nutrition 0.000 description 17
• 239000012312 sodium hydride Substances 0.000 description 17
• 229910000104 sodium hydride Inorganic materials 0.000 description 17
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
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• 229910052943 magnesium sulfate Inorganic materials 0.000 description 15
• 235000019341 magnesium sulphate Nutrition 0.000 description 15
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
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• 235000011152 sodium sulphate Nutrition 0.000 description 15
• 239000002253 acid Substances 0.000 description 14
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• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
• 150000002009 diols Chemical group 0.000 description 11
• 239000007788 liquid Substances 0.000 description 11
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
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