CA2542220A1

CA2542220A1 - Novel mch receptor antagonists

Novel mch receptor antagonists Download PDF

Info

Publication number: CA2542220A1
Authority: CA; Canada
Prior art keywords: group; phenoxy; oxadiazol; alkyl; ethylsulfanylmethyl
Prior art date: 2003-10-22
Legal status : Abandoned

Application number

CA002542220A

Other languages

English (en)

French (fr)

Inventor

James Ronald Gillig

Michael Dean Kinnick

John Michael Junior Morin

Martinez Antonio Navarro

Current Assignee

Eli Lilly and Co

Original Assignee

Individual

Priority date

2003-10-22

Filing date

2004-10-21

Publication date

2005-05-06

2004-10-21 Application filed by Individual filed Critical Individual

2005-05-06 Publication of CA2542220A1 publication Critical patent/CA2542220A1/en

Status Abandoned legal-status Critical Current

Links

102000029828 Melanin-concentrating hormone receptor Human genes 0.000 title description 5
108010047068 Melanin-concentrating hormone receptor Proteins 0.000 title description 5
229940044551 receptor antagonist Drugs 0.000 title description 2
239000002464 receptor antagonist Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 151
208000008589 Obesity Diseases 0.000 claims abstract description 21
235000020824 obesity Nutrition 0.000 claims abstract description 21
101800002739 Melanin-concentrating hormone Proteins 0.000 claims abstract description 15
150000003839 salts Chemical class 0.000 claims abstract description 15
ORRDHOMWDPJSNL-UHFFFAOYSA-N melanin concentrating hormone Chemical compound N1C(=O)C(C(C)C)NC(=O)C(CCCNC(N)=N)NC(=O)CNC(=O)C(C(C)C)NC(=O)C(CCSC)NC(=O)C(NC(=O)C(CCCNC(N)=N)NC(=O)C(NC(=O)C(NC(=O)C(N)CC(O)=O)C(C)O)CCSC)CSSCC(C(=O)NC(CC=2C3=CC=CC=C3NC=2)C(=O)NC(CCC(O)=O)C(=O)NC(C(C)C)C(O)=O)NC(=O)C2CCCN2C(=O)C(CCCNC(N)=N)NC(=O)C1CC1=CC=C(O)C=C1 ORRDHOMWDPJSNL-UHFFFAOYSA-N 0.000 claims abstract description 4
102000047659 melanin-concentrating hormone Human genes 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims description 76
-1 -O-aryl Chemical group 0.000 claims description 70
239000000203 mixture Substances 0.000 claims description 47
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
125000003118 aryl group Chemical group 0.000 claims description 41
125000000217 alkyl group Chemical group 0.000 claims description 35
229910052760 oxygen Inorganic materials 0.000 claims description 33
125000000623 heterocyclic group Chemical group 0.000 claims description 26
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 22
229910052717 sulfur Chemical group 0.000 claims description 21
125000005647 linker group Chemical group 0.000 claims description 20
229910052757 nitrogen Inorganic materials 0.000 claims description 19
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 18
125000005843 halogen group Chemical group 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 17
125000000753 cycloalkyl group Chemical group 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
125000002877 alkyl aryl group Chemical group 0.000 claims description 15
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 14
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
125000003342 alkenyl group Chemical group 0.000 claims description 12
125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 12
201000010099 disease Diseases 0.000 claims description 11
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 10
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 10
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 10
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 10
239000003814 drug Substances 0.000 claims description 10
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 10
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
125000001188 haloalkyl group Chemical group 0.000 claims description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
239000001301 oxygen Substances 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
MVWGDEIHAMVCEQ-UHFFFAOYSA-N n,n-dimethyl-1-[1-methylsulfonyl-6-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]indol-2-yl]methanamine Chemical compound C1=C2N(S(C)(=O)=O)C(CN(C)C)=CC2=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 MVWGDEIHAMVCEQ-UHFFFAOYSA-N 0.000 claims description 8
125000001624 naphthyl group Chemical group 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
125000004429 atom Chemical group 0.000 claims description 7
125000004122 cyclic group Chemical group 0.000 claims description 7
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 6
ROYQQLMXAJXHOL-UHFFFAOYSA-N 5-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]-2-(2-piperidin-1-ylethyl)-3h-isoindol-1-one Chemical compound C1C2=CC(C=3OC(CSCCOC=4C=CC=CC=4)=NN=3)=CC=C2C(=O)N1CCN1CCCCC1 ROYQQLMXAJXHOL-UHFFFAOYSA-N 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
FGDTVLQNKWSOJO-UHFFFAOYSA-N n,n-dimethyl-1-[1-methylsulfonyl-5-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]indol-2-yl]methanamine Chemical compound C=1C=C2N(S(C)(=O)=O)C(CN(C)C)=CC2=CC=1C(O1)=NN=C1CSCCOC1=CC=CC=C1 FGDTVLQNKWSOJO-UHFFFAOYSA-N 0.000 claims description 6
CRPQTFQASNDDOH-UHFFFAOYSA-N n,n-dimethyl-1-[6-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]naphthalen-2-yl]methanamine Chemical compound C1=CC2=CC(CN(C)C)=CC=C2C=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 CRPQTFQASNDDOH-UHFFFAOYSA-N 0.000 claims description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
125000004043 oxo group Chemical group O=* 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
125000002950 monocyclic group Chemical group 0.000 claims description 5
125000002971 oxazolyl group Chemical group 0.000 claims description 5
239000012453 solvate Substances 0.000 claims description 5
125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
125000004438 haloalkoxy group Chemical group 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 4
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
UWTZXSGHOKFTGN-UHFFFAOYSA-N n,n-dimethyl-1-[1-methyl-6-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]indol-2-yl]methanamine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=C2N(C)C(CN(C)C)=CC2=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 UWTZXSGHOKFTGN-UHFFFAOYSA-N 0.000 claims description 4
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
239000011593 sulfur Chemical group 0.000 claims description 4
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 4
FSMMEMQGALTDON-BTJKTKAUSA-N (z)-but-2-enedioic acid;2-(2-phenoxyethylsulfanylmethyl)-5-[6-(pyrrolidin-1-ylmethyl)naphthalen-2-yl]-1,3,4-oxadiazole Chemical compound OC(=O)\C=C/C(O)=O.C=1C=CC=CC=1OCCSCC(O1)=NN=C1C(C=C1C=C2)=CC=C1C=C2CN1CCCC1 FSMMEMQGALTDON-BTJKTKAUSA-N 0.000 claims description 3
OZDJLVULJQFTLE-UHFFFAOYSA-N 2-(2-phenoxyethylsulfanylmethyl)-5-[6-(piperidin-1-ylmethyl)naphthalen-2-yl]-1,3,4-oxadiazole Chemical compound C=1C=CC=CC=1OCCSCC(O1)=NN=C1C(C=C1C=C2)=CC=C1C=C2CN1CCCCC1 OZDJLVULJQFTLE-UHFFFAOYSA-N 0.000 claims description 3
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
FVZSEZORVQWGNL-UHFFFAOYSA-N n,n-dimethyl-1-[1-methyl-5-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]indol-3-yl]methanamine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=C2C(CN(C)C)=CN(C)C2=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 FVZSEZORVQWGNL-UHFFFAOYSA-N 0.000 claims description 3
GTGMJBRHGYLFMK-UHFFFAOYSA-N n,n-dimethyl-1-[5-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]-1-benzofuran-2-yl]methanamine;oxalic acid Chemical compound OC(=O)C(O)=O.C=1C=C2OC(CN(C)C)=CC2=CC=1C(O1)=NN=C1CSCCOC1=CC=CC=C1 GTGMJBRHGYLFMK-UHFFFAOYSA-N 0.000 claims description 3
KXXVTHPNMUULHT-UHFFFAOYSA-N n,n-dimethyl-1-[6-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]-1-benzofuran-2-yl]methanamine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=C2OC(CN(C)C)=CC2=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 KXXVTHPNMUULHT-UHFFFAOYSA-N 0.000 claims description 3
ZUYUUAIKJFTKND-UHFFFAOYSA-N n,n-dimethyl-4-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]naphthalen-1-amine Chemical compound C12=CC=CC=C2C(N(C)C)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 ZUYUUAIKJFTKND-UHFFFAOYSA-N 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 3
101100244083 Arabidopsis thaliana PKL gene Proteins 0.000 claims description 2
101100134925 Gallus gallus COR6 gene Proteins 0.000 claims description 2
101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 2
125000005518 carboxamido group Chemical group 0.000 claims description 2
125000001072 heteroaryl group Chemical group 0.000 claims description 2
230000002401 inhibitory effect Effects 0.000 claims description 2
VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical compound C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 claims description 2
MEQGXPXYVTZVHQ-UHFFFAOYSA-N n,n-dimethyl-1-[6-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]-1h-indol-2-yl]methanamine Chemical compound C1=C2NC(CN(C)C)=CC2=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 MEQGXPXYVTZVHQ-UHFFFAOYSA-N 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
239000000651 prodrug Substances 0.000 claims description 2
229940002612 prodrug Drugs 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
BDJAEZRIGNCQBZ-UHFFFAOYSA-N methylcyclobutane Chemical compound CC1CCC1 BDJAEZRIGNCQBZ-UHFFFAOYSA-N 0.000 claims 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims 2
GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
125000002393 azetidinyl group Chemical group 0.000 claims 1
PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims 1
VNXBKJFUJUWOCW-UHFFFAOYSA-N methylcyclopropane Chemical compound CC1CC1 VNXBKJFUJUWOCW-UHFFFAOYSA-N 0.000 claims 1
125000003386 piperidinyl group Chemical group 0.000 claims 1
206010012601 diabetes mellitus Diseases 0.000 abstract description 7
239000003667 hormone antagonist Substances 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 92
238000010168 coupling process Methods 0.000 description 75
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 73
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
239000007787 solid Substances 0.000 description 56
239000000243 solution Substances 0.000 description 56
238000005859 coupling reaction Methods 0.000 description 53
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 49
230000008569 process Effects 0.000 description 48
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 47
238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 47
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
239000002904 solvent Substances 0.000 description 44
230000008878 coupling Effects 0.000 description 41
238000005160 1H NMR spectroscopy Methods 0.000 description 39
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
238000007429 general method Methods 0.000 description 36
238000004587 chromatography analysis Methods 0.000 description 34
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239000003921 oil Substances 0.000 description 31
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239000002585 base Substances 0.000 description 28
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
235000019439 ethyl acetate Nutrition 0.000 description 26
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238000002360 preparation method Methods 0.000 description 25
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HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
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UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 16
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
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RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
238000010626 work up procedure Methods 0.000 description 12
GKQLYSROISKDLL-UHFFFAOYSA-N EEDQ Chemical compound C1=CC=C2N(C(=O)OCC)C(OCC)C=CC2=C1 GKQLYSROISKDLL-UHFFFAOYSA-N 0.000 description 11
102400001132 Melanin-concentrating hormone Human genes 0.000 description 11
239000002253 acid Substances 0.000 description 11
238000005755 formation reaction Methods 0.000 description 11
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 11
230000000269 nucleophilic effect Effects 0.000 description 11
230000006103 sulfonylation Effects 0.000 description 11
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 10
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
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238000005804 alkylation reaction Methods 0.000 description 10
239000012267 brine Substances 0.000 description 10
239000004202 carbamide Substances 0.000 description 10
239000003054 catalyst Substances 0.000 description 10
239000003153 chemical reaction reagent Substances 0.000 description 10
150000002148 esters Chemical class 0.000 description 10
150000003891 oxalate salts Chemical class 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
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