IL171566A - Pyrimidine derivatives useful for the treatment of diseases mediated by crth2 and medicament comprising the same - Google Patents

Info

Publication number

IL171566A

IL171566A IL171566A IL17156605A IL171566A IL 171566 A IL171566 A IL 171566A IL 171566 A IL171566 A IL 171566A IL 17156605 A IL17156605 A IL 17156605A IL 171566 A IL171566 A IL 171566A

Authority

IL

Israel

Prior art keywords

amino

benzyl

acetic acid

chloro

dimethylamino

Prior art date

2003-04-25

Links

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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 20
• 150000003230 pyrimidines Chemical class 0.000 title claims description 16
• 201000010099 disease Diseases 0.000 title claims description 15
• 238000011282 treatment Methods 0.000 title claims description 14
• 239000003814 drug Substances 0.000 title claims description 12
• 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 3
• 230000001404 mediated effect Effects 0.000 title description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 398
• -1 nitro, guanidino, pyrrolyl Chemical group 0.000 claims description 205
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 160
• 150000001875 compounds Chemical class 0.000 claims description 155
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 120
• 239000002253 acid Substances 0.000 claims description 84
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 79
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 57
• 125000000217 alkyl group Chemical group 0.000 claims description 50
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 36
• 229910052736 halogen Inorganic materials 0.000 claims description 30
• 102000009389 Prostaglandin D receptors Human genes 0.000 claims description 28
• 108050000258 Prostaglandin D receptors Proteins 0.000 claims description 28
• 230000000694 effects Effects 0.000 claims description 23
• 229910052739 hydrogen Inorganic materials 0.000 claims description 23
• 239000001257 hydrogen Substances 0.000 claims description 23
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 22
• 125000003545 alkoxy group Chemical group 0.000 claims description 20
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 18
• 150000003839 salts Chemical class 0.000 claims description 18
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
• 150000002431 hydrogen Chemical group 0.000 claims description 14
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 125000003118 aryl group Chemical group 0.000 claims description 12
• 150000002148 esters Chemical class 0.000 claims description 12
• 239000004480 active ingredient Substances 0.000 claims description 11
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
• 125000001072 heteroaryl group Chemical group 0.000 claims description 9
• 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 125000003282 alkyl amino group Chemical group 0.000 claims description 8
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 150000002367 halogens Chemical group 0.000 claims description 8
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
• 125000002541 furyl group Chemical group 0.000 claims description 7
• 125000001041 indolyl group Chemical group 0.000 claims description 7
• 125000001624 naphthyl group Chemical group 0.000 claims description 7
• 150000002825 nitriles Chemical group 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 125000001424 substituent group Chemical group 0.000 claims description 7
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 6
• 125000004414 alkyl thio group Chemical group 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 125000005493 quinolyl group Chemical group 0.000 claims description 6
• 208000032671 Allergic granulomatous angiitis Diseases 0.000 claims description 5
• 208000006344 Churg-Strauss Syndrome Diseases 0.000 claims description 5
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 5
• 208000018428 Eosinophilic granulomatosis with polyangiitis Diseases 0.000 claims description 5
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 5
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
• 201000010105 allergic rhinitis Diseases 0.000 claims description 5
• 208000006673 asthma Diseases 0.000 claims description 5
• 201000008937 atopic dermatitis Diseases 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
• 201000009890 sinusitis Diseases 0.000 claims description 5
• 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 claims description 4
• 208000016557 Acute basophilic leukemia Diseases 0.000 claims description 4
• 206010052568 Urticaria chronic Diseases 0.000 claims description 4
• 125000003705 anilinocarbonyl group Chemical group O=C([*])N([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000001589 carboacyl group Chemical group 0.000 claims description 4
• 208000024376 chronic urticaria Diseases 0.000 claims description 4
• 206010024378 leukocytosis Diseases 0.000 claims description 4
• CUNNBJJEJUDKNN-UHFFFAOYSA-N 2-[4-chloro-6-(dimethylamino)-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=N1 CUNNBJJEJUDKNN-UHFFFAOYSA-N 0.000 claims description 3
• 125000002672 4-bromobenzoyl group Chemical group BrC1=CC=C(C(=O)*)C=C1 0.000 claims description 3
• 125000002391 4-chlorocinnamoyl group Chemical group 0.000 claims description 3
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
• 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 3
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 230000002265 prevention Effects 0.000 claims description 3
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
• PTVJXKKBDDFIEH-UHFFFAOYSA-N 2-[2-[[4-[(4-fluorobenzoyl)amino]phenyl]methyl]-4-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound N1=C(N2CCCC2)C(CC(=O)O)=CN=C1CC(C=C1)=CC=C1NC(=O)C1=CC=C(F)C=C1 PTVJXKKBDDFIEH-UHFFFAOYSA-N 0.000 claims description 2
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
• 208000010668 atopic eczema Diseases 0.000 claims description 2
• 125000001246 bromo group Chemical group Br* 0.000 claims description 2
• 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 2
• 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 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
• 239000011734 sodium Substances 0.000 claims description 2
• 229910052708 sodium Inorganic materials 0.000 claims description 2
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
• 208000035475 disorder Diseases 0.000 claims 5
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
• 125000002638 (E)-4-(trifluoromethyl)cinnamoyl group Chemical group FC(C1=CC=C(/C=C/C(=O)*)C=C1)(F)F 0.000 claims 1
• MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 claims 1
• YBKWXSXHGJHDKJ-UHFFFAOYSA-N 2-[2-[(4-benzamidophenyl)methyl]-4-chloro-6-[[2-(cyclopentylamino)-2-oxoethyl]-methylamino]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=CC(NC(=O)C=3C=CC=CC=3)=CC=2)=NC(Cl)=C(CC(O)=O)C=1N(C)CC(=O)NC1CCCC1 YBKWXSXHGJHDKJ-UHFFFAOYSA-N 0.000 claims 1
• WDYCRZAIFVIUEV-UHFFFAOYSA-N 2-[2-[[4-[(4-bromobenzoyl)amino]phenyl]methyl]-4-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=CC(Br)=CC=3)=CC=2)=N1 WDYCRZAIFVIUEV-UHFFFAOYSA-N 0.000 claims 1
• LACBHKONDFDLLO-UHFFFAOYSA-N 2-[2-[[4-[(4-chlorobenzoyl)amino]phenyl]methyl]-4-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=CC(Cl)=CC=3)=CC=2)=N1 LACBHKONDFDLLO-UHFFFAOYSA-N 0.000 claims 1
• YTMBTJPYTXLXLT-UHFFFAOYSA-N 2-[2-[[4-[(4-chlorobenzoyl)amino]phenyl]methyl]-4-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound N1=C(N2CCCC2)C(CC(=O)O)=CN=C1CC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 YTMBTJPYTXLXLT-UHFFFAOYSA-N 0.000 claims 1
• VIADXYASLLIBBI-NTEUORMPSA-N 2-[2-[[4-[[(e)-3-(4-chlorophenyl)prop-2-enoyl]amino]phenyl]methyl]-4,6-bis(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound CN(C)C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)\C=C\C=3C=CC(Cl)=CC=3)=CC=2)=N1 VIADXYASLLIBBI-NTEUORMPSA-N 0.000 claims 1
• HRFIBVDUAZPDBR-UHFFFAOYSA-N 2-[4,6-bis(dimethylamino)-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound CN(C)C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=N1 HRFIBVDUAZPDBR-UHFFFAOYSA-N 0.000 claims 1
• KXPAVCJDTRYMRP-UHFFFAOYSA-N 2-[4,6-dichloro-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound N1=C(Cl)C(CC(=O)O)=C(Cl)N=C1CC(C=C1)=CC=C1NC(=O)C1=CC=C(C=CC=C2)C2=C1 KXPAVCJDTRYMRP-UHFFFAOYSA-N 0.000 claims 1
• JQMMXIYSINFBCU-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[[4-[(4-nitrophenyl)methoxycarbonylamino]phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)OCC=3C=CC(=CC=3)[N+]([O-])=O)=CC=2)=N1 JQMMXIYSINFBCU-UHFFFAOYSA-N 0.000 claims 1
• KZCGWNVWJRIYQZ-MDWZMJQESA-N 2-[4-(dimethylamino)-2-[[4-[[(e)-3-(4-methoxyphenyl)prop-2-enoyl]amino]phenyl]methyl]-6-morpholin-4-ylpyrimidin-5-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1\C=C\C(=O)NC(C=C1)=CC=C1CC1=NC(N(C)C)=C(CC(O)=O)C(N2CCOCC2)=N1 KZCGWNVWJRIYQZ-MDWZMJQESA-N 0.000 claims 1
• IWDZLCBGILKSMO-SDNWHVSQSA-N 2-[4-(dimethylamino)-6-methyl-2-[[4-[[(e)-3-phenylprop-2-enoyl]amino]phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)\C=C\C=3C=CC=CC=3)=CC=2)=N1 IWDZLCBGILKSMO-SDNWHVSQSA-N 0.000 claims 1
• FZZZSCVAJSHOTP-UHFFFAOYSA-N 2-[4-[[2-(cyclopentylamino)-2-oxoethyl]-methylamino]-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=NC=C(CC(O)=O)C=1N(C)CC(=O)NC1CCCC1 FZZZSCVAJSHOTP-UHFFFAOYSA-N 0.000 claims 1
• WXARHGJSLJJRPG-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(4-chlorobenzoyl)amino]phenyl]methyl]-6-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound N1=C(N2CCCC2)C(CC(=O)O)=C(Cl)N=C1CC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 WXARHGJSLJJRPG-UHFFFAOYSA-N 0.000 claims 1
• HVTPKJKYFNCJTQ-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(4-cyanobenzoyl)amino]phenyl]methyl]-6-[[2-(cyclopentylamino)-2-oxoethyl]-methylamino]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=CC(NC(=O)C=3C=CC(=CC=3)C#N)=CC=2)=NC(Cl)=C(CC(O)=O)C=1N(C)CC(=O)NC1CCCC1 HVTPKJKYFNCJTQ-UHFFFAOYSA-N 0.000 claims 1
• YXGOGRZMDMUOGA-JLHYYAGUSA-N 2-[4-chloro-2-[[4-[[(e)-3-phenylprop-2-enoyl]amino]phenyl]methyl]-6-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound N1=C(N2CCCC2)C(CC(=O)O)=C(Cl)N=C1CC(C=C1)=CC=C1NC(=O)\C=C\C1=CC=CC=C1 YXGOGRZMDMUOGA-JLHYYAGUSA-N 0.000 claims 1
• JDIZIXSBVMDTGP-UHFFFAOYSA-N 2-[4-chloro-6-(3-hydroxypyrrolidin-1-yl)-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound C1C(O)CCN1C1=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=NC(Cl)=C1CC(O)=O JDIZIXSBVMDTGP-UHFFFAOYSA-N 0.000 claims 1
• BFMGMGYWQIAUDB-UHFFFAOYSA-N 2-[4-chloro-6-(dimethylamino)-2-[[4-(1h-indole-6-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=C4NC=CC4=CC=3)=CC=2)=N1 BFMGMGYWQIAUDB-UHFFFAOYSA-N 0.000 claims 1
• BKKCKMSIZYLPNF-UHFFFAOYSA-N 2-[4-chloro-6-[2-methoxyethyl(methyl)amino]-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)C(N(C)CCOC)=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=N1 BKKCKMSIZYLPNF-UHFFFAOYSA-N 0.000 claims 1
• OVWALNLURHWQRX-UHFFFAOYSA-N 2-[4-chloro-6-[[2-(cyclopentylamino)-2-oxoethyl]-methylamino]-2-[[4-(quinoline-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=CC(NC(=O)C=3N=C4C=CC=CC4=CC=3)=CC=2)=NC(Cl)=C(CC(O)=O)C=1N(C)CC(=O)NC1CCCC1 OVWALNLURHWQRX-UHFFFAOYSA-N 0.000 claims 1
• QQMRDTNQAFALAD-UHFFFAOYSA-N 2-[4-chloro-6-[[2-(cyclopentylamino)-2-oxoethyl]-methylamino]-2-[[4-[(4-methylbenzoyl)amino]phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=CC(NC(=O)C=3C=CC(C)=CC=3)=CC=2)=NC(Cl)=C(CC(O)=O)C=1N(C)CC(=O)NC1CCCC1 QQMRDTNQAFALAD-UHFFFAOYSA-N 0.000 claims 1
• NLWYDXUIACZZHR-DTQAZKPQSA-N 2-[4-chloro-6-[[2-(cyclopentylamino)-2-oxoethyl]-methylamino]-2-[[4-[[(e)-3-phenylprop-2-enoyl]amino]phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=CC(NC(=O)\C=C\C=3C=CC=CC=3)=CC=2)=NC(Cl)=C(CC(O)=O)C=1N(C)CC(=O)NC1CCCC1 NLWYDXUIACZZHR-DTQAZKPQSA-N 0.000 claims 1
• JCCWVFAUVIWOGL-UHFFFAOYSA-N 2-[4-chloro-6-[methyl-(2-oxo-2-pyrrolidin-1-ylethyl)amino]-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=NC(Cl)=C(CC(O)=O)C=1N(C)CC(=O)N1CCCC1 JCCWVFAUVIWOGL-UHFFFAOYSA-N 0.000 claims 1
• 125000002999 4-(trifluoromethyl)benzoyl group Chemical group FC(C1=CC=C(C(=O)*)C=C1)(F)F 0.000 claims 1
• RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 1
• 229940124003 CRTH2 antagonist Drugs 0.000 claims 1
• 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims 1
• 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 claims 1
• 241001465754 Metazoa Species 0.000 claims 1
• 230000000172 allergic effect Effects 0.000 claims 1
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
• SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical group NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 claims 1
• 238000006243 chemical reaction Methods 0.000 description 87
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• 239000002904 solvent Substances 0.000 description 34
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
• 239000000243 solution Substances 0.000 description 32
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• 239000000203 mixture Substances 0.000 description 26
• 210000004027 cell Anatomy 0.000 description 24
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
• 239000007787 solid Substances 0.000 description 22
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