NZ532624A - Alpha2delta ligands to treat tinnitus - Google Patents

Info

Publication number

NZ532624A

NZ532624A NZ532624A NZ53262403A NZ532624A NZ 532624 A NZ532624 A NZ 532624A NZ 532624 A NZ532624 A NZ 532624A NZ 53262403 A NZ53262403 A NZ 53262403A NZ 532624 A NZ532624 A NZ 532624A

Authority

NZ

New Zealand

Prior art keywords

aminomethyl

methyl

acid

mmol

compound

Prior art date

2002-01-31

Links

• Espacenet
• Global Dossier
• Discuss

• 208000009205 Tinnitus Diseases 0.000 title claims abstract description 27
• 231100000886 tinnitus Toxicity 0.000 title claims abstract description 26
• 239000003446 ligand Substances 0.000 title abstract description 46
• 150000001875 compounds Chemical class 0.000 claims abstract description 237
• 150000003839 salts Chemical class 0.000 claims abstract description 59
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 46
• 239000001257 hydrogen Substances 0.000 claims abstract description 34
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 34
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 28
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
• 239000003814 drug Substances 0.000 claims abstract description 13
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
• -1 3-aminomethyl-bicyclo[3.2.0]hept-3-yl Chemical group 0.000 claims description 99
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 81
• 229960000583 acetic acid Drugs 0.000 claims description 73
• 239000002253 acid Substances 0.000 claims description 59
• 238000011282 treatment Methods 0.000 claims description 48
• 238000002360 preparation method Methods 0.000 claims description 41
• 241000124008 Mammalia Species 0.000 claims description 8
• KKXFMWXZXDUYBF-BDAKNGLRSA-N (3s,5r)-3-(aminomethyl)-5-methyloctanoic acid Chemical compound CCC[C@@H](C)C[C@H](CN)CC(O)=O KKXFMWXZXDUYBF-BDAKNGLRSA-N 0.000 claims description 7
• AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 claims description 7
• 229960001233 pregabalin Drugs 0.000 claims description 5
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 3
• 229910052717 sulfur Inorganic materials 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims 1
• 239000000546 pharmaceutical excipient Substances 0.000 claims 1
• UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 abstract description 24
• 229960002870 gabapentin Drugs 0.000 abstract description 5
• 238000004519 manufacturing process Methods 0.000 abstract 1
• PBJUNZJWGZTSKL-MRXNPFEDSA-N tiagabine Chemical compound C1=CSC(C(=CCCN2C[C@@H](CCC2)C(O)=O)C2=C(C=CS2)C)=C1C PBJUNZJWGZTSKL-MRXNPFEDSA-N 0.000 abstract 1
• 229960001918 tiagabine Drugs 0.000 abstract 1
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 366
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 325
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 246
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 219
• 239000000243 solution Substances 0.000 description 212
• 238000000034 method Methods 0.000 description 160
• 239000000203 mixture Substances 0.000 description 150
• 239000003921 oil Substances 0.000 description 144
• 235000019198 oils Nutrition 0.000 description 144
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 133
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 130
• 235000019439 ethyl acetate Nutrition 0.000 description 126
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 117
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 114
• 229910001868 water Inorganic materials 0.000 description 113
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 112
• 238000005481 NMR spectroscopy Methods 0.000 description 105
• 239000002904 solvent Substances 0.000 description 96
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 90
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 81
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 79
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 78
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 77
• 239000007787 solid Substances 0.000 description 76
• 238000003786 synthesis reaction Methods 0.000 description 73
• 238000006243 chemical reaction Methods 0.000 description 72
• 230000015572 biosynthetic process Effects 0.000 description 68
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 65
• 239000012267 brine Substances 0.000 description 63
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 60
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 58
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 58
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 57
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 57
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
• 230000002829 reductive effect Effects 0.000 description 49
• 239000000047 product Substances 0.000 description 47
• 238000003756 stirring Methods 0.000 description 44
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 43
• 239000010410 layer Substances 0.000 description 40
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 38
• 238000010992 reflux Methods 0.000 description 38
• 239000011541 reaction mixture Substances 0.000 description 37
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 34
• 239000012074 organic phase Substances 0.000 description 34
• 238000000746 purification Methods 0.000 description 33
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 31
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 30
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
• 229910000104 sodium hydride Inorganic materials 0.000 description 30
• 229940086542 triethylamine Drugs 0.000 description 30
• 150000002148 esters Chemical class 0.000 description 28
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 27
• 239000012230 colorless oil Substances 0.000 description 26
• 238000001704 evaporation Methods 0.000 description 26
• 239000000725 suspension Substances 0.000 description 26
• 230000008020 evaporation Effects 0.000 description 25
• 239000000284 extract Substances 0.000 description 25
• 238000003818 flash chromatography Methods 0.000 description 25
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 24
• 150000003951 lactams Chemical class 0.000 description 24
• 101150041968 CDC13 gene Proteins 0.000 description 23
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 23
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 23
• 229920006395 saturated elastomer Polymers 0.000 description 23
• 239000000377 silicon dioxide Substances 0.000 description 23
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
• 239000008346 aqueous phase Substances 0.000 description 22
• 239000000706 filtrate Substances 0.000 description 22
• 239000012071 phase Substances 0.000 description 22
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 22
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 21
• OFUQZEVBAUYZJB-HTQZYQBOSA-N (3r,4r)-3,4-dimethyl-1-(2h-tetrazol-5-ylmethyl)cyclopentane-1-carbonitrile Chemical compound C1[C@@H](C)[C@H](C)CC1(C#N)CC1=NN=NN1 OFUQZEVBAUYZJB-HTQZYQBOSA-N 0.000 description 20
• 239000002585 base Substances 0.000 description 20
• 239000003153 chemical reaction reagent Substances 0.000 description 20
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 19
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 19
• 229910052786 argon Inorganic materials 0.000 description 19
• 239000003054 catalyst Substances 0.000 description 19
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 18
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 18
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
• LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 18
• 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 17
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 16
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 16
• 238000004458 analytical method Methods 0.000 description 16
• 239000000741 silica gel Substances 0.000 description 16
• 229910002027 silica gel Inorganic materials 0.000 description 16
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
• VLRQRRQHXZCEDL-UHFFFAOYSA-N 2-cyclohexylideneacetonitrile Chemical compound N#CC=C1CCCCC1 VLRQRRQHXZCEDL-UHFFFAOYSA-N 0.000 description 15
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 15
• 239000007864 aqueous solution Substances 0.000 description 15
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
• 238000001914 filtration Methods 0.000 description 15
• 235000019341 magnesium sulphate Nutrition 0.000 description 15
• 150000001412 amines Chemical class 0.000 description 14
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 14
• 238000004587 chromatography analysis Methods 0.000 description 14
• BLTGCCZCXNKAPX-UHFFFAOYSA-N ethyl 3-(bromomethyl)-5-methylhexanoate Chemical compound CCOC(=O)CC(CBr)CC(C)C BLTGCCZCXNKAPX-UHFFFAOYSA-N 0.000 description 14
• 229940116254 phosphonic acid Drugs 0.000 description 14
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 14
• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 13
• KKXFMWXZXDUYBF-UHFFFAOYSA-N 3-(aminomethyl)-5-methyloctanoic acid Chemical compound CCCC(C)CC(CN)CC(O)=O KKXFMWXZXDUYBF-UHFFFAOYSA-N 0.000 description 13
• JVVRCYWZTJLJSG-UHFFFAOYSA-N 4-dimethylaminophenol Chemical compound CN(C)C1=CC=C(O)C=C1 JVVRCYWZTJLJSG-UHFFFAOYSA-N 0.000 description 13
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 13
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-dimethylaminopyridine Substances CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 13
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 13
• CJMFUZSVUFPYJR-UHFFFAOYSA-N [2-(aminomethyl)-4-methylpentyl]phosphonic acid Chemical compound CC(C)CC(CN)CP(O)(O)=O CJMFUZSVUFPYJR-UHFFFAOYSA-N 0.000 description 13
• 150000001413 amino acids Chemical class 0.000 description 13
• 239000012298 atmosphere Substances 0.000 description 13
• 125000000623 heterocyclic group Chemical group 0.000 description 13
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 13
• AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 13
• 239000012312 sodium hydride Substances 0.000 description 13
• GXLDCDIGAKAJSB-UHFFFAOYSA-N tert-butyl n-[[1-(2-amino-2-oxoethyl)cyclohexyl]methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1(CC(N)=O)CCCCC1 GXLDCDIGAKAJSB-UHFFFAOYSA-N 0.000 description 13
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
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• 229910052757 nitrogen Inorganic materials 0.000 description 12
• 239000012044 organic layer Substances 0.000 description 12
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 11
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• 125000006239 protecting group Chemical group 0.000 description 11
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 10
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
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• MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 10
• 229940125782 compound 2 Drugs 0.000 description 10
• UNOSJPBCPKCIJI-UHFFFAOYSA-N ethyl 3-(diethoxyphosphorylmethyl)-5-methylhexanoate Chemical compound CCOC(=O)CC(CC(C)C)CP(=O)(OCC)OCC UNOSJPBCPKCIJI-UHFFFAOYSA-N 0.000 description 10
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• JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 10
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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 10
• 230000002378 acidificating effect Effects 0.000 description 9
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• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
• SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 8
• BGQCKHBIIZKBJU-UHFFFAOYSA-N 3-(aminomethyl)-5,7-dimethyloctanoic acid Chemical compound CC(C)CC(C)CC(CN)CC(O)=O BGQCKHBIIZKBJU-UHFFFAOYSA-N 0.000 description 7
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 7
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• 150000007513 acids Chemical class 0.000 description 7
• SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 7
• 229940125904 compound 1 Drugs 0.000 description 7
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• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
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• 239000012280 lithium aluminium hydride Substances 0.000 description 7
• 229910052751 metal Inorganic materials 0.000 description 7
• 239000002184 metal Substances 0.000 description 7
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