KR20040081478A - 이명을 치료하기 위한 알파 2 델타 리간드 - Google Patents
이명을 치료하기 위한 알파 2 델타 리간드 Download PDFInfo
- Publication number
- KR20040081478A KR20040081478A KR10-2004-7011809A KR20047011809A KR20040081478A KR 20040081478 A KR20040081478 A KR 20040081478A KR 20047011809 A KR20047011809 A KR 20047011809A KR 20040081478 A KR20040081478 A KR 20040081478A
- Authority
- KR
- South Korea
- Prior art keywords
- aminomethyl
- methyl
- acid
- formula
- acetic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
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- 239000003446 ligand Substances 0.000 title claims abstract description 56
- 208000009205 Tinnitus Diseases 0.000 title claims abstract description 25
- 231100000886 tinnitus Toxicity 0.000 title claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 236
- 238000000034 method Methods 0.000 claims abstract description 165
- 150000003839 salts Chemical class 0.000 claims abstract description 66
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 43
- 239000001257 hydrogen Substances 0.000 claims abstract description 41
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 3
- -1 hydroxy, carboxy Chemical group 0.000 claims description 143
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 118
- 239000002253 acid Substances 0.000 claims description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims description 40
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
- BIGWXAGEQONZGD-UHFFFAOYSA-N 2h-oxadiazol-5-one Chemical compound O=C1C=NNO1 BIGWXAGEQONZGD-UHFFFAOYSA-N 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 claims description 15
- NDDZVQRQVFTNSN-UHFFFAOYSA-N 2-[3-(aminomethyl)-3-bicyclo[3.2.0]heptanyl]acetic acid Chemical compound C1C(CN)(CC(O)=O)CC2CCC21 NDDZVQRQVFTNSN-UHFFFAOYSA-N 0.000 claims description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
- 150000001408 amides Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 229940124530 sulfonamide Drugs 0.000 claims description 10
- 150000003456 sulfonamides Chemical group 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 9
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical group C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 7
- 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 6
- CWSXPZYRFGYVBO-UHFFFAOYSA-N 4-methyl-2-(2h-tetrazol-5-ylmethyl)pentan-1-amine Chemical compound CC(C)CC(CN)CC1=NN=NN1 CWSXPZYRFGYVBO-UHFFFAOYSA-N 0.000 claims description 6
- CJMFUZSVUFPYJR-UHFFFAOYSA-N [2-(aminomethyl)-4-methylpentyl]phosphonic acid Chemical compound CC(C)CC(CN)CP(O)(O)=O CJMFUZSVUFPYJR-UHFFFAOYSA-N 0.000 claims description 6
- 229960002870 gabapentin Drugs 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- BKHFSUPPXXUOLT-UHFFFAOYSA-N 3-[2-(aminomethyl)-4-methylpentyl]-2h-1,2,4-oxadiazole-5-thione Chemical compound CC(C)CC(CN)CC1=NOC(=S)N1 BKHFSUPPXXUOLT-UHFFFAOYSA-N 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 229960001233 pregabalin Drugs 0.000 claims description 4
- MOEZPHHJIZLEKX-UHFFFAOYSA-N 3-[[1-(aminomethyl)cyclohexyl]methyl]-2h-1,2,4-oxadiazol-5-one Chemical compound N=1OC(=O)NC=1CC1(CN)CCCCC1 MOEZPHHJIZLEKX-UHFFFAOYSA-N 0.000 claims description 3
- QFLSQUNSWXMJBE-UHFFFAOYSA-N [1-(aminomethyl)cyclohexyl]methylphosphonic acid Chemical compound OP(=O)(O)CC1(CN)CCCCC1 QFLSQUNSWXMJBE-UHFFFAOYSA-N 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 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 description 2
- OUYPRNJUXRLDLW-UHFFFAOYSA-N 3-(3-amino-2-cyclobutylpropyl)-2h-1,2,4-thiadiazol-5-one Chemical compound C1CCC1C(CN)CC1=NSC(=O)N1 OUYPRNJUXRLDLW-UHFFFAOYSA-N 0.000 claims description 2
- XRTLNMMGRKQIQZ-UHFFFAOYSA-N 3-(3-amino-2-cyclopentylpropyl)-2h-1,2,4-thiadiazol-5-one Chemical compound C1CCCC1C(CN)CC1=NSC(=O)N1 XRTLNMMGRKQIQZ-UHFFFAOYSA-N 0.000 claims description 2
- YRQVDEYJCBOBGQ-UHFFFAOYSA-N 3-[[1-(aminomethyl)cycloheptyl]methyl]-2h-1,2,4-oxadiazol-5-one;hydrochloride Chemical compound Cl.N=1OC(=O)NC=1CC1(CN)CCCCCC1 YRQVDEYJCBOBGQ-UHFFFAOYSA-N 0.000 claims description 2
- IHLRLJMHYXJRST-UHFFFAOYSA-N 3-[[1-(aminomethyl)cyclohexyl]methyl]-2h-1,2,4-oxadiazol-5-one;hydrochloride Chemical compound Cl.N=1OC(=O)NC=1CC1(CN)CCCCC1 IHLRLJMHYXJRST-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- PPIQMYQQPKTQBZ-UHFFFAOYSA-N n-[2-[1-(aminomethyl)cyclohexyl]ethyl]methanesulfonamide Chemical compound CS(=O)(=O)NCCC1(CN)CCCCC1 PPIQMYQQPKTQBZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000006502 nitrobenzyl group Chemical group 0.000 claims description 2
- 239000000651 prodrug Substances 0.000 claims description 2
- 229940002612 prodrug Drugs 0.000 claims description 2
- 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 2
- HCQGVISMHVQRMT-UHFFFAOYSA-N 2-(3-amino-5-methyl-3-bicyclo[3.2.0]heptanyl)acetic acid Chemical compound C1C(N)(CC(O)=O)CC2(C)C1CC2 HCQGVISMHVQRMT-UHFFFAOYSA-N 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 330
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 303
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 254
- 239000000243 solution Substances 0.000 description 221
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 213
- 239000000203 mixture Substances 0.000 description 161
- 239000003921 oil Substances 0.000 description 142
- 235000019198 oils Nutrition 0.000 description 142
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 135
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 130
- 235000019439 ethyl acetate Nutrition 0.000 description 118
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 113
- 239000002904 solvent Substances 0.000 description 99
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 96
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 87
- 239000007787 solid Substances 0.000 description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 76
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 76
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 75
- 238000003786 synthesis reaction Methods 0.000 description 75
- 230000015572 biosynthetic process Effects 0.000 description 72
- 238000006243 chemical reaction Methods 0.000 description 72
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 71
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 71
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 67
- 239000012267 brine Substances 0.000 description 65
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 60
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 60
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
- 230000002829 reductive effect Effects 0.000 description 52
- 239000000047 product Substances 0.000 description 48
- 150000003951 lactams Chemical class 0.000 description 44
- 238000002360 preparation method Methods 0.000 description 44
- 239000010410 layer Substances 0.000 description 43
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 41
- 238000003756 stirring Methods 0.000 description 41
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 40
- 239000011541 reaction mixture Substances 0.000 description 39
- 229920006395 saturated elastomer Polymers 0.000 description 38
- 239000012074 organic phase Substances 0.000 description 36
- 238000010992 reflux Methods 0.000 description 35
- 239000000460 chlorine Substances 0.000 description 33
- 238000000746 purification Methods 0.000 description 32
- 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 31
- 238000007792 addition Methods 0.000 description 31
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 31
- 229940086542 triethylamine Drugs 0.000 description 31
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
- 150000002148 esters Chemical class 0.000 description 30
- VLVOEGVIDIDILV-RKDXNWHRSA-N ethyl 2-cyano-2-[(3r,4r)-3,4-dimethylcyclopentylidene]acetate Chemical compound CCOC(=O)C(C#N)=C1C[C@@H](C)[C@H](C)C1 VLVOEGVIDIDILV-RKDXNWHRSA-N 0.000 description 28
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 28
- 239000012230 colorless oil Substances 0.000 description 27
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 26
- 239000008346 aqueous phase Substances 0.000 description 26
- 239000011734 sodium Substances 0.000 description 26
- 229910000104 sodium hydride Inorganic materials 0.000 description 26
- 239000000725 suspension Substances 0.000 description 26
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 25
- 239000000284 extract Substances 0.000 description 25
- 230000008569 process Effects 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 238000001704 evaporation Methods 0.000 description 24
- 239000000706 filtrate Substances 0.000 description 23
- 239000000377 silicon dioxide Substances 0.000 description 23
- 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 23
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 22
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 22
- ORDRYYZMZDILKB-SCLLHFNJSA-N [(3r,4r)-3,4-dimethyl-1-(2h-tetrazol-5-ylmethyl)cyclopentyl]methanamine;hydrochloride Chemical compound Cl.C1[C@@H](C)[C@H](C)CC1(CN)CC1=NN=NN1 ORDRYYZMZDILKB-SCLLHFNJSA-N 0.000 description 22
- 239000003054 catalyst Substances 0.000 description 22
- 230000008020 evaporation Effects 0.000 description 22
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 22
- 150000001241 acetals Chemical class 0.000 description 21
- 238000003818 flash chromatography Methods 0.000 description 21
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 21
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 20
- 229910052786 argon Inorganic materials 0.000 description 20
- 239000002585 base Substances 0.000 description 20
- 239000012071 phase Substances 0.000 description 20
- HOFBIVOLROWHNN-UHFFFAOYSA-N n-[2-[1-(aminomethyl)cyclohexyl]ethyl]methanesulfonamide;hydrochloride Chemical compound Cl.CS(=O)(=O)NCCC1(CN)CCCCC1 HOFBIVOLROWHNN-UHFFFAOYSA-N 0.000 description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 229910004298 SiO 2 Inorganic materials 0.000 description 18
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 17
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
- 150000001412 amines Chemical class 0.000 description 16
- 239000003153 chemical reaction reagent Substances 0.000 description 16
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 16
- 239000000741 silica gel Substances 0.000 description 16
- 229910002027 silica gel Inorganic materials 0.000 description 16
- 150000001540 azides Chemical class 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
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 15
- 235000019341 magnesium sulphate Nutrition 0.000 description 15
- 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 14
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 14
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 14
- 238000001816 cooling Methods 0.000 description 14
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 13
- 150000001413 amino acids Chemical class 0.000 description 13
- 239000012298 atmosphere Substances 0.000 description 13
- 150000002596 lactones Chemical class 0.000 description 13
- 229910052763 palladium Inorganic materials 0.000 description 13
- POJPAKDTOHEIBC-UHFFFAOYSA-N 1-benzyl-4-(2-methylpentyl)pyrrolidin-2-one Chemical compound O=C1CC(CC(C)CCC)CN1CC1=CC=CC=C1 POJPAKDTOHEIBC-UHFFFAOYSA-N 0.000 description 12
- ONKWZNBXHSMMDK-UHFFFAOYSA-N 2-[2-(aminomethyl)-1,3,3a,4,5,6,7,7a-octahydroinden-2-yl]acetic acid Chemical compound C1CCCC2CC(CN)(CC(O)=O)CC21 ONKWZNBXHSMMDK-UHFFFAOYSA-N 0.000 description 12
- KKXFMWXZXDUYBF-UHFFFAOYSA-N 3-(aminomethyl)-5-methyloctanoic acid Chemical compound CCCC(C)CC(CN)CC(O)=O KKXFMWXZXDUYBF-UHFFFAOYSA-N 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 12
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- 229940126214 compound 3 Drugs 0.000 description 11
- 150000004820 halides Chemical class 0.000 description 11
- 239000012312 sodium hydride Substances 0.000 description 11
- NBINUAYUYGRPPJ-UHFFFAOYSA-N 2-[3-(aminomethyl)-3-bicyclo[3.2.0]heptanyl]acetic acid;hydrochloride Chemical compound Cl.C1C(CN)(CC(O)=O)CC2CCC21 NBINUAYUYGRPPJ-UHFFFAOYSA-N 0.000 description 10
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 10
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 10
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 10
- 229940125782 compound 2 Drugs 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 10
- IASDTUBNBCYCJG-YUMQZZPRSA-N (3r,4s)-3-(azaniumylmethyl)-4,5-dimethylhexanoate Chemical compound CC(C)[C@H](C)[C@H](CN)CC(O)=O IASDTUBNBCYCJG-YUMQZZPRSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
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- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
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- BIRWKKXCRCFMKP-HROGELHOSA-N tert-butyl (3s,5r)-5-methyl-3-[(4r,5s)-4-methyl-2-oxo-5-phenyl-1,3-oxazolidine-3-carbonyl]nonanoate Chemical compound O1C(=O)N(C(=O)[C@H](CC(=O)OC(C)(C)C)C[C@H](C)CCCC)[C@H](C)[C@@H]1C1=CC=CC=C1 BIRWKKXCRCFMKP-HROGELHOSA-N 0.000 description 1
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- GSRYOMXTHAIEMA-WBQJQJEBSA-N tert-butyl (3s,5s)-5-methyl-3-[(4r,5s)-4-methyl-2-oxo-5-phenyl-1,3-oxazolidine-3-carbonyl]heptanoate Chemical compound O1C(=O)N(C(=O)[C@H](CC(=O)OC(C)(C)C)C[C@@H](C)CC)[C@H](C)[C@@H]1C1=CC=CC=C1 GSRYOMXTHAIEMA-WBQJQJEBSA-N 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
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- CKKRXPQJUIYKTF-UHFFFAOYSA-N tert-butyl n-[2-[[1-(2-cyanoethyl)tetrazol-5-yl]methyl]-4-methylpentyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC(CC(C)C)CC1=NN=NN1CCC#N CKKRXPQJUIYKTF-UHFFFAOYSA-N 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
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- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/131—Amines acyclic
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K31/13—Amines
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4245—Oxadiazoles
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/443—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with oxygen as a ring hetero atom
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- A—HUMAN NECESSITIES
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A61K31/662—Phosphorus acids or esters thereof having P—C bonds, e.g. foscarnet, trichlorfon
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35363202P | 2002-01-31 | 2002-01-31 | |
| US60/353,632 | 2002-01-31 | ||
| PCT/IB2003/000232 WO2003063845A1 (en) | 2002-01-31 | 2003-01-20 | Alpha 2 delta ligands to treat tinnitus |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20040081478A true KR20040081478A (ko) | 2004-09-21 |
Family
ID=27663234
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR10-2004-7011809A Ceased KR20040081478A (ko) | 2002-01-31 | 2003-01-20 | 이명을 치료하기 위한 알파 2 델타 리간드 |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US7026505B2 (https=) |
| EP (1) | EP1469841A1 (https=) |
| JP (1) | JP2005521664A (https=) |
| KR (1) | KR20040081478A (https=) |
| CN (1) | CN1625393A (https=) |
| AU (1) | AU2003201716B2 (https=) |
| BR (1) | BR0307411A (https=) |
| CA (1) | CA2474000A1 (https=) |
| CL (1) | CL2008000613A1 (https=) |
| IL (1) | IL162028A0 (https=) |
| MX (1) | MXPA04004105A (https=) |
| NZ (1) | NZ532624A (https=) |
| PL (1) | PL371944A1 (https=) |
| TW (1) | TW200306177A (https=) |
| WO (1) | WO2003063845A1 (https=) |
| ZA (1) | ZA200403069B (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL126999A (en) | 1996-07-24 | 2002-03-10 | Warner Lambert Co | Pharmaceutical preparations containing isobutylgaba and its history for use in the treatment of pain |
| US8048917B2 (en) | 2005-04-06 | 2011-11-01 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| WO2004078734A1 (en) | 2003-03-07 | 2004-09-16 | Warner-Lambert Company Llc | TETRAZOLE AND OXADIAZOLONE SUBSTITUTED β-AMINO ACID DERIVATIVES |
| NZ543102A (en) | 2003-04-24 | 2008-12-24 | Incyte Corp | Aza spiro alkane derivatives as inhibitors of metalloproteases |
| WO2005013888A2 (en) * | 2003-05-14 | 2005-02-17 | Cytokinetics, Inc. | Compounds, compositions and methods |
| CN101506140B (zh) * | 2006-08-24 | 2014-06-18 | 百时美施贵宝公司 | 环状11β-羟类固醇脱氢酶Ⅰ型抑制剂 |
| US7727978B2 (en) | 2006-08-24 | 2010-06-01 | Bristol-Myers Squibb Company | Cyclic 11-beta hydroxysteroid dehydrogenase type I inhibitors |
| US20080188562A1 (en) * | 2006-11-14 | 2008-08-07 | Noa Zerangue | Treating tinnitus using prodrugs of gabapentin and pregabalin |
| WO2008073257A1 (en) * | 2006-12-08 | 2008-06-19 | Xenoport, Inc. | Use of prodrugs of gaba analogs for treating diseases |
| ITMI20071492A1 (it) | 2007-07-24 | 2009-01-25 | S I I T Srl Servizio Internazi | "composizioni per il trattamento e la prevenzione di condizioni di vertigine e acufeni comprendenti citicolina, estratto di ginkgo biloba e flavoni dimerici di ginkgo biloba" |
| US8119658B2 (en) | 2007-10-01 | 2012-02-21 | Bristol-Myers Squibb Company | Triazolopyridine 11-beta hydroxysteroid dehydrogenase type I inhibitors |
| CN101260063B (zh) * | 2008-03-21 | 2013-06-19 | 北京润德康医药技术有限公司 | γ-氨基丁酸衍生物及其制备方法 |
| JP2010043063A (ja) | 2008-05-09 | 2010-02-25 | Agency For Science Technology & Research | 川崎病の診断及び治療 |
| CN111718379A (zh) * | 2019-03-19 | 2020-09-29 | 海南长安国际制药有限公司 | 具有l1和l2结构的铂类物质及其制备方法和应用 |
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| DE2460891C2 (de) | 1974-12-21 | 1982-09-23 | Gödecke AG, 1000 Berlin | 1-Aminomethyl-1-cycloalkanessigsäuren und deren Ester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US4087544A (en) | 1974-12-21 | 1978-05-02 | Warner-Lambert Company | Treatment of cranial dysfunctions using novel cyclic amino acids |
| US6197819B1 (en) * | 1990-11-27 | 2001-03-06 | Northwestern University | Gamma amino butyric acid analogs and optical isomers |
| ATE361909T1 (de) * | 1996-10-23 | 2007-06-15 | Warner Lambert Co | Substituierte gamma-aminobuttersäurederivate als arzneimittel |
| CA2304967C (en) * | 1997-12-16 | 2005-06-14 | Warner-Lambert Company | 4(3)substituted-4(3)-aminomethyl-(thio)pyran or -piperidine derivatives (=gabapentin analogues), their preparation and their use in the treatment of neurological disorders |
| SI1045839T1 (en) * | 1997-12-16 | 2004-06-30 | Warner-Lambert Company Llc | Novel amines as pharmaceutical agents |
| CN1131855C (zh) * | 1997-12-16 | 2003-12-24 | 沃尼尔·朗伯公司 | 1－取代－1－氨基甲基－环烷衍生物(=加巴喷丁类似物)、其制备及其在治疗神经病方面的用途 |
| WO1999061424A1 (en) * | 1998-05-26 | 1999-12-02 | Warner-Lambert Company | Conformationally constrained amino acid compounds having affinity for the alpha2delta subunit of a calcium channel |
| GB9821179D0 (en) * | 1998-09-30 | 1998-11-25 | Merck Sharp & Dohme | Therapeutic use |
| ES2317839T3 (es) * | 1999-06-10 | 2009-05-01 | Warner-Lambert Company Llc | Acidos 3-propil gamma-aminobutiricos monosustituidos. |
| HN2000000224A (es) * | 1999-10-20 | 2001-04-11 | Warner Lambert Co | Aminoacidos biciclicos como agentes farmaceuticos |
| US6620829B2 (en) * | 2000-10-17 | 2003-09-16 | Warner-Lambert Company | Method of treating noninflammatory cartilage damage |
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2003
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- 2003-01-20 JP JP2003563539A patent/JP2005521664A/ja not_active Withdrawn
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- 2003-01-20 MX MXPA04004105A patent/MXPA04004105A/es active IP Right Grant
- 2003-01-20 CA CA002474000A patent/CA2474000A1/en not_active Abandoned
- 2003-01-20 CN CNA038031388A patent/CN1625393A/zh active Pending
- 2003-01-20 KR KR10-2004-7011809A patent/KR20040081478A/ko not_active Ceased
- 2003-01-20 IL IL16202803A patent/IL162028A0/xx unknown
- 2003-01-20 WO PCT/IB2003/000232 patent/WO2003063845A1/en not_active Ceased
- 2003-01-20 NZ NZ532624A patent/NZ532624A/en unknown
- 2003-01-20 EP EP03700417A patent/EP1469841A1/en not_active Ceased
- 2003-01-20 PL PL03371944A patent/PL371944A1/xx not_active Application Discontinuation
- 2003-01-29 US US10/353,367 patent/US7026505B2/en not_active Expired - Fee Related
- 2003-01-30 TW TW092102235A patent/TW200306177A/zh unknown
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2004
- 2004-04-22 ZA ZA200403069A patent/ZA200403069B/en unknown
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2005
- 2005-12-21 US US11/314,126 patent/US7138542B2/en not_active Expired - Fee Related
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| MXPA04004105A (es) | 2004-11-29 |
| BR0307411A (pt) | 2004-12-07 |
| IL162028A0 (en) | 2005-11-20 |
| US7026505B2 (en) | 2006-04-11 |
| CL2008000613A1 (es) | 2008-11-07 |
| WO2003063845A1 (en) | 2003-08-07 |
| EP1469841A1 (en) | 2004-10-27 |
| ZA200403069B (en) | 2005-04-22 |
| CN1625393A (zh) | 2005-06-08 |
| NZ532624A (en) | 2007-05-31 |
| JP2005521664A (ja) | 2005-07-21 |
| PL371944A1 (en) | 2005-07-11 |
| CA2474000A1 (en) | 2003-08-07 |
| US20060100281A1 (en) | 2006-05-11 |
| TW200306177A (en) | 2003-11-16 |
| US7138542B2 (en) | 2006-11-21 |
| AU2003201716B2 (en) | 2008-04-17 |
| US20030176504A1 (en) | 2003-09-18 |
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