BRPI0721127A2 - Derivados indol como agonistas de receptor s1p1 - Google Patents

Info

Publication number

BRPI0721127A2

BRPI0721127A2 BRPI0721127-9A BRPI0721127A BRPI0721127A2 BR PI0721127 A2 BRPI0721127 A2 BR PI0721127A2 BR PI0721127 A BRPI0721127 A BR PI0721127A BR PI0721127 A2 BRPI0721127 A2 BR PI0721127A2

Authority

BR

Brazil

Prior art keywords

indol

oxadiazol

phenyl

acid

chloro

Prior art date

2006-12-21

Links

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• 101710155454 Sphingosine 1-phosphate receptor 1 Proteins 0.000 title claims description 10
• 102100025750 Sphingosine 1-phosphate receptor 1 Human genes 0.000 title claims description 10
• 239000000556 agonist Substances 0.000 title description 10
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title description 8
• 150000001875 compounds Chemical class 0.000 claims description 209
• -1 trifluoromethoxy, difluoromethoxy Chemical group 0.000 claims description 122
• 229910052739 hydrogen Inorganic materials 0.000 claims description 88
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 82
• 239000002253 acid Substances 0.000 claims description 78
• 238000000034 method Methods 0.000 claims description 56
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 51
• 150000003839 salts Chemical class 0.000 claims description 41
• 239000001257 hydrogen Substances 0.000 claims description 39
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 28
• 229910052736 halogen Inorganic materials 0.000 claims description 28
• 150000002367 halogens Chemical class 0.000 claims description 27
• 102000011011 Sphingosine 1-phosphate receptors Human genes 0.000 claims description 26
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 25
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
• 108050001083 Sphingosine 1-phosphate receptors Proteins 0.000 claims description 22
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 21
• 125000001424 substituent group Chemical group 0.000 claims description 19
• 125000000217 alkyl group Chemical group 0.000 claims description 18
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
• 238000011282 treatment Methods 0.000 claims description 18
• 208000035475 disorder Diseases 0.000 claims description 14
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 11
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 11
• 125000003545 alkoxy group Chemical group 0.000 claims description 11
• 201000010099 disease Diseases 0.000 claims description 10
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
• 206010028980 Neoplasm Diseases 0.000 claims description 8
• 230000002757 inflammatory effect Effects 0.000 claims description 8
• 230000001404 mediated effect Effects 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 125000004178 (C1-C4) alkyl group Chemical class 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 7
• 239000011737 fluorine Substances 0.000 claims description 7
• 229910052731 fluorine Inorganic materials 0.000 claims description 7
• 201000006417 multiple sclerosis Diseases 0.000 claims description 7
• DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 7
• 235000019260 propionic acid Nutrition 0.000 claims description 7
• 238000002054 transplantation Methods 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 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 5
• 150000003235 pyrrolidines Chemical class 0.000 claims description 5
• 108020003175 receptors Proteins 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• 208000023275 Autoimmune disease Diseases 0.000 claims description 4
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 4
• 208000011231 Crohn disease Diseases 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 206010027476 Metastases Diseases 0.000 claims description 4
• 201000004681 Psoriasis Diseases 0.000 claims description 4
• 206010063837 Reperfusion injury Diseases 0.000 claims description 4
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 4
• 230000001154 acute effect Effects 0.000 claims description 4
• 230000033115 angiogenesis Effects 0.000 claims description 4
• 206010003246 arthritis Diseases 0.000 claims description 4
• 208000006673 asthma Diseases 0.000 claims description 4
• 208000037976 chronic inflammation Diseases 0.000 claims description 4
• 208000037893 chronic inflammatory disorder Diseases 0.000 claims description 4
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
• 125000001153 fluoro group Chemical group F* 0.000 claims description 4
• 230000000302 ischemic effect Effects 0.000 claims description 4
• 230000009401 metastasis Effects 0.000 claims description 4
• 201000001119 neuropathy Diseases 0.000 claims description 4
• 230000007823 neuropathy Effects 0.000 claims description 4
• 102000005962 receptors Human genes 0.000 claims description 4
• 208000019553 vascular disease Diseases 0.000 claims description 4
• 230000003612 virological effect Effects 0.000 claims description 4
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 3
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
• 125000005843 halogen group Chemical group 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 150000003053 piperidines Chemical class 0.000 claims description 3
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 3
• STYIZLCKMLBTSK-UHFFFAOYSA-N 1-nitropiperidine-2-carbonitrile Chemical compound C(#N)C1N(CCCC1)[N+](=O)[O-] STYIZLCKMLBTSK-UHFFFAOYSA-N 0.000 claims description 2
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• JNCSFNYUKWYUDF-UHFFFAOYSA-N 2-[4-[5-(3-cyano-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]acetic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CC(O)=O)C=3C=CC=2)=NO1 JNCSFNYUKWYUDF-UHFFFAOYSA-N 0.000 claims description 2
• QFOCXKVUZZDCDL-UHFFFAOYSA-N 3-[5-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=C3C=CN(CCC(O)=O)C3=CC=2)=NO1 QFOCXKVUZZDCDL-UHFFFAOYSA-N 0.000 claims description 2
• NCZWOHWUDJLURH-UHFFFAOYSA-N 4-[4-[5-[3-chloro-4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=CC=C2N(CCCC(=O)O)C=CC2=C1C(N=1)=NOC=1C1=CC=C(OC(F)(F)F)C(Cl)=C1 NCZWOHWUDJLURH-UHFFFAOYSA-N 0.000 claims description 2
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• GPIGQTXSVJRXGM-UHFFFAOYSA-N 3-[3-chloro-5-[5-[6-(4-fluorophenyl)pyridin-3-yl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C=1C=C2N(CCC(=O)O)C=C(Cl)C2=CC=1C(N=1)=NOC=1C(C=N1)=CC=C1C1=CC=C(F)C=C1 GPIGQTXSVJRXGM-UHFFFAOYSA-N 0.000 claims 2
• RYCURDRPWHCXQR-AWEZNQCLSA-N (2s)-3-[5-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]-2-methylpropanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=C3C=CN(C[C@H](C)C(O)=O)C3=CC=2)=NO1 RYCURDRPWHCXQR-AWEZNQCLSA-N 0.000 claims 1
• JDKAJAKVJGLQIO-UHFFFAOYSA-N 2,2-dimethyl-3-[5-[5-[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C=1C=C2N(CC(C)(C)C(O)=O)C=CC2=CC=1C(N=1)=NOC=1C(SC=1C(F)(F)F)=CC=1C1=CC=CC=C1 JDKAJAKVJGLQIO-UHFFFAOYSA-N 0.000 claims 1
• QDKQSBXYKYZLMW-UHFFFAOYSA-N 2-[4-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CC(O)=O)C=3C=CC=2)=NO1 QDKQSBXYKYZLMW-UHFFFAOYSA-N 0.000 claims 1
• IHFJSTWVWRLHRP-UHFFFAOYSA-N 3-[3-chloro-4-[5-[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=CC=C2N(CCC(=O)O)C=C(Cl)C2=C1C(N=1)=NOC=1C(SC=1C(F)(F)F)=CC=1C1=CC=CC=C1 IHFJSTWVWRLHRP-UHFFFAOYSA-N 0.000 claims 1
• HVTSNKVSHMFPKV-UHFFFAOYSA-N 3-[3-chloro-5-[5-(3-chloro-4-propoxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(Cl)C(OCCC)=CC=C1C1=NC(C=2C=C3C(Cl)=CN(CCC(O)=O)C3=CC=2)=NO1 HVTSNKVSHMFPKV-UHFFFAOYSA-N 0.000 claims 1
• XHSNHDLFBNSHHH-UHFFFAOYSA-N 3-[3-chloro-5-[5-[3-chloro-4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C=1C=C2N(CCC(=O)O)C=C(Cl)C2=CC=1C(N=1)=NOC=1C1=CC=C(OC(F)(F)F)C(Cl)=C1 XHSNHDLFBNSHHH-UHFFFAOYSA-N 0.000 claims 1
• JWIKJHGBIFHLPM-UHFFFAOYSA-N 3-[4-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CCC(O)=O)C=3C=CC=2)=NO1 JWIKJHGBIFHLPM-UHFFFAOYSA-N 0.000 claims 1
• XAJVGJHOAIETSC-UHFFFAOYSA-N 3-[4-[5-(3-cyano-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CCC(O)=O)C=3C=CC=2)=NO1 XAJVGJHOAIETSC-UHFFFAOYSA-N 0.000 claims 1
• QIHAASGINXICIX-UHFFFAOYSA-N 3-[4-[5-[4-(2-fluorophenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=CC=C2N(CCC(=O)O)C=CC2=C1C(N=1)=NOC=1C(C=C1C(F)(F)F)=CC=C1C1=CC=CC=C1F QIHAASGINXICIX-UHFFFAOYSA-N 0.000 claims 1
• FONMSGPEBHUUIV-UHFFFAOYSA-N 3-[4-[5-[4-cyclohexyl-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=CC=C2N(CCC(=O)O)C=CC2=C1C(N=1)=NOC=1C(C=C1C(F)(F)F)=CC=C1C1CCCCC1 FONMSGPEBHUUIV-UHFFFAOYSA-N 0.000 claims 1
• NORSCQNGKKVMIO-UHFFFAOYSA-N 3-[4-[5-[4-phenyl-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=CC=C2N(CCC(=O)O)C=CC2=C1C(N=1)=NOC=1C(C=C1C(F)(F)F)=CC=C1C1=CC=CC=C1 NORSCQNGKKVMIO-UHFFFAOYSA-N 0.000 claims 1
• YYMNUTARGZMIAY-UHFFFAOYSA-N 3-[4-[5-[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid propanoic acid Chemical compound C1(=CC=CC=C1)C=1C=C(SC1C(F)(F)F)C1=NC(=NO1)C1=C2C=CN(C2=CC=C1)CCC(=O)O.C(CC)(=O)O YYMNUTARGZMIAY-UHFFFAOYSA-N 0.000 claims 1
• GVFAFIKUOWUAIQ-UHFFFAOYSA-N 3-[4-[5-[4-propan-2-yloxy-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(C(F)(F)F)C(OC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CCC(O)=O)C=3C=CC=2)=NO1 GVFAFIKUOWUAIQ-UHFFFAOYSA-N 0.000 claims 1
• JXFAYGCVJMEDKI-UHFFFAOYSA-N 3-[5-[5-(3-cyano-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1C1=NC(C=2C=C3C=CN(CCC(O)=O)C3=CC=2)=NO1 JXFAYGCVJMEDKI-UHFFFAOYSA-N 0.000 claims 1
• KTEBETLGEOJCSN-UHFFFAOYSA-N 3-[5-[5-(4-phenylthiophen-2-yl)-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid 3-[5-[5-[3-phenyl-4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]indol-1-yl]propanoic acid Chemical compound C1(=CC=CC=C1)C=1C=C(SC1)C1=NC(=NO1)C=1C=C2C=CN(C2=CC1)CCC(=O)O.FC(C1=CC=C(C=C1C1=CC=CC=C1)C1=NC(=NO1)C=1C=C2C=CN(C2=CC1)CCC(=O)O)(F)F KTEBETLGEOJCSN-UHFFFAOYSA-N 0.000 claims 1
• SKMHVWFGAFXNPS-UHFFFAOYSA-N 4-[4-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CCCC(O)=O)C=3C=CC=2)=NO1 SKMHVWFGAFXNPS-UHFFFAOYSA-N 0.000 claims 1
• UHURKDFLIMINLN-UHFFFAOYSA-N 4-[4-[5-(3-cyano-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1C1=NC(C=2C=3C=CN(CCCC(O)=O)C=3C=CC=2)=NO1 UHURKDFLIMINLN-UHFFFAOYSA-N 0.000 claims 1
• NFIGDBFIDKDNIG-UHFFFAOYSA-N 4-[4-[5-(5-chloro-6-propan-2-yloxypyridin-3-yl)-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=NC=C1C1=NC(C=2C=3C=CN(CCCC(O)=O)C=3C=CC=2)=NO1 NFIGDBFIDKDNIG-UHFFFAOYSA-N 0.000 claims 1
• CRVGFMNPKAVZLK-UHFFFAOYSA-N 4-[4-[5-[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=CC=C2N(CCCC(=O)O)C=CC2=C1C(N=1)=NOC=1C(SC=1C(F)(F)F)=CC=1C1=CC=CC=C1 CRVGFMNPKAVZLK-UHFFFAOYSA-N 0.000 claims 1
• HLDBXISXBVARTO-UHFFFAOYSA-N 4-[5-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=C3C=CN(CCCC(O)=O)C3=CC=2)=NO1 HLDBXISXBVARTO-UHFFFAOYSA-N 0.000 claims 1
• VXNIDFMYHIAKQT-UHFFFAOYSA-N 5-[5-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]indol-1-yl]pentanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC(C=2C=C3C=CN(CCCCC(O)=O)C3=CC=2)=NO1 VXNIDFMYHIAKQT-UHFFFAOYSA-N 0.000 claims 1
• HHJRTTLWJFMCGJ-UHFFFAOYSA-N C(#N)C1=C(C=CC(=C1)C1=NC(=NO1)C1=C2C=CN(C2=CC=C1)CCCC(=O)O)C1=CC=CC=C1.C(#N)C=1C=C(C=CC1CC(C)C)C1=NC(=NO1)C1=C2C=CN(C2=CC=C1)CCCC(=O)O Chemical compound C(#N)C1=C(C=CC(=C1)C1=NC(=NO1)C1=C2C=CN(C2=CC=C1)CCCC(=O)O)C1=CC=CC=C1.C(#N)C=1C=C(C=CC1CC(C)C)C1=NC(=NO1)C1=C2C=CN(C2=CC=C1)CCCC(=O)O HHJRTTLWJFMCGJ-UHFFFAOYSA-N 0.000 claims 1
• HGFOFHRQIDSJNF-UHFFFAOYSA-N CCC(C(O)=O)N1C2=CC=CC(C3=NOC(C(C=C4)=CC(C(F)(F)F)=C4C4=CC=CC=C4)=N3)=C2C=C1 Chemical compound CCC(C(O)=O)N1C2=CC=CC(C3=NOC(C(C=C4)=CC(C(F)(F)F)=C4C4=CC=CC=C4)=N3)=C2C=C1 HGFOFHRQIDSJNF-UHFFFAOYSA-N 0.000 claims 1
• VGAJWLUXQVSFLA-UHFFFAOYSA-N ClC1=CN(C2=CC=C(C=C12)C1=NOC(=N1)C1=CC(=C(C=C1)OC)Cl)CCC Chemical compound ClC1=CN(C2=CC=C(C=C12)C1=NOC(=N1)C1=CC(=C(C=C1)OC)Cl)CCC VGAJWLUXQVSFLA-UHFFFAOYSA-N 0.000 claims 1
• 241000124008 Mammalia Species 0.000 claims 1
• QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical compound [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 258
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 210
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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 114
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• 239000000203 mixture Substances 0.000 description 107
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• 238000006243 chemical reaction Methods 0.000 description 76
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• 239000011541 reaction mixture Substances 0.000 description 62
• 235000019441 ethanol Nutrition 0.000 description 57
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 50
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 42
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• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
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• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 31
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• 239000012071 phase Substances 0.000 description 30
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• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
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