TW200306177A - Method of treating tinnitus - Google Patents

Info

Publication number

TW200306177A

TW200306177A TW092102235A TW92102235A TW200306177A TW 200306177 A TW200306177 A TW 200306177A TW 092102235 A TW092102235 A TW 092102235A TW 92102235 A TW92102235 A TW 92102235A TW 200306177 A TW200306177 A TW 200306177A

Authority

TW

Taiwan

Prior art keywords

acid

methyl

aminomethyl

aminemethyl

acetic acid

Prior art date

2002-01-31

Links

• Espacenet
• Global Dossier
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• 208000009205 Tinnitus Diseases 0.000 title claims abstract description 18
• 231100000886 tinnitus Toxicity 0.000 title claims abstract description 18
• 238000000034 method Methods 0.000 title abstract description 156
• 150000001875 compounds Chemical class 0.000 claims abstract description 233
• 150000003839 salts Chemical class 0.000 claims abstract description 64
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 35
• 239000003446 ligand Substances 0.000 claims abstract description 31
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
• -1 1-aminomethyl-cyclohexylmethyl Chemical group 0.000 claims description 346
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 196
• 239000000203 mixture Substances 0.000 claims description 148
• 239000002253 acid Substances 0.000 claims description 146
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 85
• 229910052799 carbon Inorganic materials 0.000 claims description 34
• 125000004432 carbon atom Chemical group C* 0.000 claims description 30
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
• 150000001412 amines Chemical class 0.000 claims description 20
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 14
• 239000000126 substance Substances 0.000 claims description 14
• UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 claims description 12
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
• 239000003814 drug Substances 0.000 claims description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 125000003545 alkoxy group Chemical group 0.000 claims description 10
• 125000004429 atom Chemical group 0.000 claims description 10
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
• 229940124530 sulfonamide Drugs 0.000 claims description 9
• 125000000623 heterocyclic group Chemical group 0.000 claims description 8
• 125000001424 substituent group Chemical group 0.000 claims description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 5
• 150000001409 amidines Chemical class 0.000 claims description 5
• 229940079593 drug Drugs 0.000 claims description 5
• 229960002870 gabapentin Drugs 0.000 claims description 5
• 125000005843 halogen group Chemical group 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 5
• AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 claims description 4
• 150000003456 sulfonamides Chemical group 0.000 claims description 4
• 241000124008 Mammalia Species 0.000 claims description 3
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 229960001233 pregabalin Drugs 0.000 claims description 3
• 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 2
• 125000003342 alkenyl group Chemical group 0.000 claims description 2
• UPCIBFUJJLCOQG-UHFFFAOYSA-L ethyl-[2-[2-[ethyl(dimethyl)azaniumyl]ethyl-methylamino]ethyl]-dimethylazanium;dibromide Chemical compound [Br-].[Br-].CC[N+](C)(C)CCN(C)CC[N+](C)(C)CC UPCIBFUJJLCOQG-UHFFFAOYSA-L 0.000 claims description 2
• 239000000651 prodrug Substances 0.000 claims description 2
• 229940002612 prodrug Drugs 0.000 claims description 2
• 125000005102 carbonylalkoxy group Chemical group 0.000 claims 3
• KKXFMWXZXDUYBF-DTWKUNHWSA-N (3r,5s)-3-(aminomethyl)-5-methyloctanoic acid Chemical compound CCC[C@H](C)C[C@@H](CN)CC(O)=O KKXFMWXZXDUYBF-DTWKUNHWSA-N 0.000 claims 1
• XZRHNAFEYMSXRG-UHFFFAOYSA-N 2,5-dimethylbenzoic acid Chemical compound CC1=CC=C(C)C(C(O)=O)=C1 XZRHNAFEYMSXRG-UHFFFAOYSA-N 0.000 claims 1
• BIGWXAGEQONZGD-UHFFFAOYSA-N 2h-oxadiazol-5-one Chemical compound O=C1C=NNO1 BIGWXAGEQONZGD-UHFFFAOYSA-N 0.000 claims 1
• 241001529936 Murinae Species 0.000 claims 1
• 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
• 208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 claims 1
• 238000010586 diagram Methods 0.000 claims 1
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
• 229940100684 pentylamine Drugs 0.000 claims 1
• 229940116254 phosphonic acid Drugs 0.000 claims 1
• 238000004611 spectroscopical analysis Methods 0.000 claims 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 claims 1
• 229960001918 tiagabine Drugs 0.000 claims 1
• 229910052739 hydrogen Inorganic materials 0.000 abstract description 28
• 239000001257 hydrogen Substances 0.000 abstract description 26
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 306
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 278
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 251
• 239000000243 solution Substances 0.000 description 201
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 198
• 229910001868 water Inorganic materials 0.000 description 155
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 147
• VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 145
• 235000019439 ethyl acetate Nutrition 0.000 description 116
• 239000002904 solvent Substances 0.000 description 106
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 91
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 88
• 238000006243 chemical reaction Methods 0.000 description 88
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 85
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 81
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 81
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 74
• 238000005481 NMR spectroscopy Methods 0.000 description 71
• 239000003921 oil Substances 0.000 description 70
• 235000019198 oils Nutrition 0.000 description 70
• 239000007787 solid Substances 0.000 description 70
• 239000000047 product Substances 0.000 description 59
• 238000003756 stirring Methods 0.000 description 58
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 56
• 238000003786 synthesis reaction Methods 0.000 description 56
• 239000012267 brine Substances 0.000 description 55
• 230000015572 biosynthetic process Effects 0.000 description 53
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
• 239000010410 layer Substances 0.000 description 51
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 49
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 48
• 101150041968 CDC13 gene Proteins 0.000 description 46
• 230000002829 reductive effect Effects 0.000 description 46
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 45
• 241001674048 Phthiraptera Species 0.000 description 44
• 150000002148 esters Chemical class 0.000 description 43
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 38
• 239000000284 extract Substances 0.000 description 37
• 230000008569 process Effects 0.000 description 37
• 239000012074 organic phase Substances 0.000 description 36
• 238000004519 manufacturing process Methods 0.000 description 34
• DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 34
• 235000019441 ethanol Nutrition 0.000 description 33
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 32
• 239000011541 reaction mixture Substances 0.000 description 32
• 238000010992 reflux Methods 0.000 description 31
• 239000000725 suspension Substances 0.000 description 31
• 238000002360 preparation method Methods 0.000 description 29
• 239000002585 base Substances 0.000 description 27
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 26
• 235000013336 milk Nutrition 0.000 description 26
• 239000008267 milk Substances 0.000 description 26
• 210000004080 milk Anatomy 0.000 description 26
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• 238000000746 purification Methods 0.000 description 26
• 229910000104 sodium hydride Inorganic materials 0.000 description 26
• 238000003818 flash chromatography Methods 0.000 description 25
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 24
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 23
• 239000008346 aqueous phase Substances 0.000 description 23
• 239000012071 phase Substances 0.000 description 23
• 238000011282 treatment Methods 0.000 description 23
• 229920006395 saturated elastomer Polymers 0.000 description 22
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 21
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 21
• 239000012230 colorless oil Substances 0.000 description 21
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 20
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
• 239000007864 aqueous solution Substances 0.000 description 20
• 239000000706 filtrate Substances 0.000 description 20
• 238000004587 chromatography analysis Methods 0.000 description 18
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 18
• 238000012360 testing method Methods 0.000 description 18
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 17
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 17
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 17
• 239000003054 catalyst Substances 0.000 description 17
• 239000007788 liquid Substances 0.000 description 17
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 16
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 16
• 235000011054 acetic acid Nutrition 0.000 description 16
• 229910052786 argon Inorganic materials 0.000 description 16
• 210000003414 extremity Anatomy 0.000 description 16
• 229960003692 gamma aminobutyric acid Drugs 0.000 description 16
• 229960002446 octanoic acid Drugs 0.000 description 16
• 239000000741 silica gel Substances 0.000 description 16
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• 241000282414 Homo sapiens Species 0.000 description 15
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• 239000003153 chemical reaction reagent Substances 0.000 description 15
• 239000003795 chemical substances by application 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
• 238000001704 evaporation Methods 0.000 description 15
• 230000008020 evaporation Effects 0.000 description 15
• 229910052740 iodine Inorganic materials 0.000 description 15
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 15
• MHPUGCYGQWGLJL-UHFFFAOYSA-N 5-methyl-hexanoic acid Chemical compound CC(C)CCCC(O)=O MHPUGCYGQWGLJL-UHFFFAOYSA-N 0.000 description 14
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• 229910052757 nitrogen Inorganic materials 0.000 description 14
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• 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 13
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• 238000001816 cooling Methods 0.000 description 13
• BLTGCCZCXNKAPX-UHFFFAOYSA-N ethyl 3-(bromomethyl)-5-methylhexanoate Chemical compound CCOC(=O)CC(CBr)CC(C)C BLTGCCZCXNKAPX-UHFFFAOYSA-N 0.000 description 13
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• 125000005916 2-methylpentyl group Chemical group 0.000 description 7
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