NZ546259A - Benzoimidazole compounds - Google Patents

Info

Publication number

NZ546259A

NZ546259A NZ546259A NZ54625904A NZ546259A NZ 546259 A NZ546259 A NZ 546259A NZ 546259 A NZ546259 A NZ 546259A NZ 54625904 A NZ54625904 A NZ 54625904A NZ 546259 A NZ546259 A NZ 546259A

Authority

NZ

New Zealand

Prior art keywords

methyl

benzoimidazole

piperidin

pyridin

butoxy

Prior art date

2003-09-30

Links

• Espacenet
• Global Dossier
• Discuss

• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title description 58
• 150000001875 compounds Chemical class 0.000 claims abstract description 287
• 239000003814 drug Substances 0.000 claims abstract description 12
• 238000002360 preparation method Methods 0.000 claims abstract description 12
• 101000585507 Solanum tuberosum Cytochrome b-c1 complex subunit 7 Proteins 0.000 claims abstract description 3
• 239000000203 mixture Substances 0.000 claims description 166
• -1 hydroxy, amino Chemical group 0.000 claims description 65
• 125000001424 substituent group Chemical group 0.000 claims description 51
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
• 230000028709 inflammatory response Effects 0.000 claims description 38
• 102000005962 receptors Human genes 0.000 claims description 35
• 108020003175 receptors Proteins 0.000 claims description 35
• 150000002148 esters Chemical class 0.000 claims description 33
• 230000004044 response Effects 0.000 claims description 33
• 150000003839 salts Chemical class 0.000 claims description 33
• 150000001408 amides Chemical class 0.000 claims description 31
• 229910052739 hydrogen Inorganic materials 0.000 claims description 27
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
• 239000008194 pharmaceutical composition Substances 0.000 claims description 22
• 210000003630 histaminocyte Anatomy 0.000 claims description 20
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
• 125000004122 cyclic group Chemical group 0.000 claims description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• 210000000265 leukocyte Anatomy 0.000 claims description 14
• 230000007115 recruitment Effects 0.000 claims description 14
• 230000003110 anti-inflammatory effect Effects 0.000 claims description 13
• 230000001404 mediated effect Effects 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 208000035475 disorder Diseases 0.000 claims description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
• 125000000623 heterocyclic group Chemical group 0.000 claims description 10
• 239000003112 inhibitor Substances 0.000 claims description 10
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
• 208000023275 Autoimmune disease Diseases 0.000 claims description 9
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 9
• 201000010105 allergic rhinitis Diseases 0.000 claims description 9
• 208000006673 asthma Diseases 0.000 claims description 9
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
• 125000005842 heteroatom Chemical group 0.000 claims description 9
• 125000003118 aryl group Chemical group 0.000 claims description 8
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 8
• 239000003396 histamine H4 receptor antagonist Substances 0.000 claims description 8
• 230000001900 immune effect Effects 0.000 claims description 8
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 125000005843 halogen group Chemical group 0.000 claims description 7
• 229910003827 NRaRb Inorganic materials 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• 230000002401 inhibitory effect Effects 0.000 claims description 6
• 229940044551 receptor antagonist Drugs 0.000 claims description 6
• 239000002464 receptor antagonist Substances 0.000 claims description 6
• 239000000126 substance Substances 0.000 claims description 6
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 5
• 201000001320 Atherosclerosis Diseases 0.000 claims description 5
• 206010020751 Hypersensitivity Diseases 0.000 claims description 5
• 208000006045 Spondylarthropathies Diseases 0.000 claims description 5
• 125000000217 alkyl group Chemical group 0.000 claims description 5
• 208000026935 allergic disease Diseases 0.000 claims description 5
• 230000009285 allergic inflammation Effects 0.000 claims description 5
• 208000010668 atopic eczema Diseases 0.000 claims description 5
• 201000004339 autoimmune neuropathy Diseases 0.000 claims description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 230000000694 effects Effects 0.000 claims description 5
• 208000027866 inflammatory disease Diseases 0.000 claims description 5
• 229940075993 receptor modulator Drugs 0.000 claims description 5
• 201000005671 spondyloarthropathy Diseases 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 4
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
• 206010047112 Vasculitides Diseases 0.000 claims description 4
• 206010047115 Vasculitis Diseases 0.000 claims description 4
• 230000006022 acute inflammation Effects 0.000 claims description 4
• 208000038016 acute inflammation Diseases 0.000 claims description 4
• 230000000172 allergic effect Effects 0.000 claims description 4
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 208000037976 chronic inflammation Diseases 0.000 claims description 4
• 230000006020 chronic inflammation Effects 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 3
• 208000003343 Antiphospholipid Syndrome Diseases 0.000 claims description 3
• 206010003827 Autoimmune hepatitis Diseases 0.000 claims description 3
• 206010050245 Autoimmune thrombocytopenia Diseases 0.000 claims description 3
• 208000009137 Behcet syndrome Diseases 0.000 claims description 3
• 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims description 3
• 208000033222 Biliary cirrhosis primary Diseases 0.000 claims description 3
• 208000011231 Crohn disease Diseases 0.000 claims description 3
• 206010012468 Dermatitis herpetiformis Diseases 0.000 claims description 3
• 208000007465 Giant cell arteritis Diseases 0.000 claims description 3
• 206010072579 Granulomatosis with polyangiitis Diseases 0.000 claims description 3
• 208000035186 Hemolytic Autoimmune Anemia Diseases 0.000 claims description 3
• 208000029462 Immunodeficiency disease Diseases 0.000 claims description 3
• 208000019693 Lung disease Diseases 0.000 claims description 3
• 208000018501 Lymphatic disease Diseases 0.000 claims description 3
• 201000011152 Pemphigus Diseases 0.000 claims description 3
• 208000031845 Pernicious anaemia Diseases 0.000 claims description 3
• 208000012654 Primary biliary cholangitis Diseases 0.000 claims description 3
• 208000003251 Pruritus Diseases 0.000 claims description 3
• 201000004681 Psoriasis Diseases 0.000 claims description 3
• 206010039710 Scleroderma Diseases 0.000 claims description 3
• 208000021386 Sjogren Syndrome Diseases 0.000 claims description 3
• 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 claims description 3
• 210000004100 adrenal gland Anatomy 0.000 claims description 3
• 230000007815 allergy Effects 0.000 claims description 3
• 201000000448 autoimmune hemolytic anemia Diseases 0.000 claims description 3
• 208000006424 autoimmune oophoritis Diseases 0.000 claims description 3
• 208000010928 autoimmune thyroid disease Diseases 0.000 claims description 3
• 201000004982 autoimmune uveitis Diseases 0.000 claims description 3
• 125000004432 carbon atom Chemical group C* 0.000 claims description 3
• 238000002512 chemotherapy Methods 0.000 claims description 3
• 230000001684 chronic effect Effects 0.000 claims description 3
• 201000001981 dermatomyositis Diseases 0.000 claims description 3
• 125000001072 heteroaryl group Chemical group 0.000 claims description 3
• 208000015181 infectious disease Diseases 0.000 claims description 3
• 230000009545 invasion Effects 0.000 claims description 3
• 206010025135 lupus erythematosus Diseases 0.000 claims description 3
• 208000018555 lymphatic system disease Diseases 0.000 claims description 3
• 201000006417 multiple sclerosis Diseases 0.000 claims description 3
• 206010028417 myasthenia gravis Diseases 0.000 claims description 3
• 201000005737 orchitis Diseases 0.000 claims description 3
• 239000004031 partial agonist Substances 0.000 claims description 3
• 201000001976 pemphigus vulgaris Diseases 0.000 claims description 3
• 208000005987 polymyositis Diseases 0.000 claims description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
• 206010043207 temporal arteritis Diseases 0.000 claims description 3
• 210000003437 trachea Anatomy 0.000 claims description 3
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 2
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 2
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 2
• 230000001363 autoimmune Effects 0.000 claims description 2
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
• 230000007823 neuropathy Effects 0.000 claims description 2
• 201000001119 neuropathy Diseases 0.000 claims description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
• 208000033808 peripheral neuropathy Diseases 0.000 claims description 2
• 229910052701 rubidium Inorganic materials 0.000 claims description 2
• LATWOSVUJSUXIW-UHFFFAOYSA-N 4,5-dimethyl-2-[2-[4-(1-methylpiperidin-4-yl)butoxy]pyridin-4-yl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCCOC1=CC(C=2NC3=CC=C(C)C(C)=C3N=2)=CC=N1 LATWOSVUJSUXIW-UHFFFAOYSA-N 0.000 claims 2
• 238000010186 staining Methods 0.000 claims 2
• MEZJODVVTDSYLU-UHFFFAOYSA-N 2-[5-bromo-2-[4-(1-methylpiperidin-4-yl)butoxy]pyridin-4-yl]-5-chloro-6-fluoro-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCCOC1=CC(C=2NC3=CC(F)=C(Cl)C=C3N=2)=C(Br)C=N1 MEZJODVVTDSYLU-UHFFFAOYSA-N 0.000 claims 1
• DUJUWDBZNGBPTK-UHFFFAOYSA-N 2-[5-chloro-2-[4-(1-methylpiperidin-4-yl)butoxy]pyridin-4-yl]-4,6-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCCOC1=CC(C=2NC3=CC(C)=CC(C)=C3N=2)=C(Cl)C=N1 DUJUWDBZNGBPTK-UHFFFAOYSA-N 0.000 claims 1
• KMRIZXCSPQLJPF-UHFFFAOYSA-N 4,6-dimethyl-2-[3-methyl-2-[4-(1-methylpiperidin-4-yl)butoxy]pyridin-4-yl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCCOC1=NC=CC(C=2NC3=CC(C)=CC(C)=C3N=2)=C1C KMRIZXCSPQLJPF-UHFFFAOYSA-N 0.000 claims 1
• DUXGDMXVDCRBBT-UHFFFAOYSA-N 4-methyl-2-[3-methyl-2-[4-(1-methylpiperidin-4-yl)butoxy]pyridin-4-yl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCCOC1=NC=CC(C=2NC3=CC=CC(C)=C3N=2)=C1C DUXGDMXVDCRBBT-UHFFFAOYSA-N 0.000 claims 1
• DDYLUTKZNHPYKL-UHFFFAOYSA-N 6-tert-butyl-2-[2-[4-(1-methylpiperidin-4-yl)butoxy]pyridin-4-yl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCCOC1=CC(C=2NC3=CC=C(C=C3N=2)C(C)(C)C)=CC=N1 DDYLUTKZNHPYKL-UHFFFAOYSA-N 0.000 claims 1
• 206010051841 Exposure to allergen Diseases 0.000 claims 1
• IXSSOWOFRKNOSO-UHFFFAOYSA-N [4-(4,6-dimethyl-1h-benzimidazol-2-yl)-6-[4-(1-methylpiperidin-4-yl)butoxy]pyridin-3-yl]methanol Chemical compound C1CN(C)CCC1CCCCOC1=CC(C=2NC3=CC(C)=CC(C)=C3N=2)=C(CO)C=N1 IXSSOWOFRKNOSO-UHFFFAOYSA-N 0.000 claims 1
• 230000006978 adaptation Effects 0.000 claims 1
• 230000004048 modification Effects 0.000 claims 1
• 238000012986 modification Methods 0.000 claims 1
• 229950003937 tolonium Drugs 0.000 claims 1
• HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 claims 1
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 254
• 238000000034 method Methods 0.000 description 199
• 238000005160 1H NMR spectroscopy Methods 0.000 description 155
• 239000000243 solution Substances 0.000 description 101
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 98
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 77
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
• 239000000284 extract Substances 0.000 description 54
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 53
• NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 45
• 238000000746 purification Methods 0.000 description 44
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 37
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 35
• 238000004128 high performance liquid chromatography Methods 0.000 description 34
• 239000011541 reaction mixture Substances 0.000 description 31
• 229910001868 water Inorganic materials 0.000 description 28
• 239000000741 silica gel Substances 0.000 description 27
• 229910002027 silica gel Inorganic materials 0.000 description 27
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 26
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• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
• 229960001340 histamine Drugs 0.000 description 25
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 25
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
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• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 17
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 16
• 238000011282 treatment Methods 0.000 description 16
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
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• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 14
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 14
• 238000004440 column chromatography Methods 0.000 description 14
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
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• 229910000104 sodium hydride Inorganic materials 0.000 description 14
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• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 13
• 239000007787 solid Substances 0.000 description 13
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• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
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• MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 11
• 229910000027 potassium carbonate Inorganic materials 0.000 description 11
• LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 11
• 239000001476 sodium potassium tartrate Substances 0.000 description 11
• 235000011006 sodium potassium tartrate Nutrition 0.000 description 11
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• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
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• SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 8
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 8
• 239000012043 crude product Substances 0.000 description 8
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• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 8
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• PJQIBTFOXWGAEN-UHFFFAOYSA-N 1,2-dimethylbenzimidazole Chemical compound C1=CC=C2N(C)C(C)=NC2=C1 PJQIBTFOXWGAEN-UHFFFAOYSA-N 0.000 description 7
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 7
• 239000005909 Kieselgur Substances 0.000 description 7
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• 239000005557 antagonist Substances 0.000 description 7
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• 235000015320 potassium carbonate Nutrition 0.000 description 7
• 239000000651 prodrug Substances 0.000 description 7
• 229940002612 prodrug Drugs 0.000 description 7
• 239000002904 solvent Substances 0.000 description 7
• 238000012360 testing method Methods 0.000 description 7
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• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
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• 229940079593 drug Drugs 0.000 description 6
• VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 6
• 150000004678 hydrides Chemical class 0.000 description 6
• 239000007788 liquid Substances 0.000 description 6
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
• 230000002265 prevention Effects 0.000 description 6
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