KR20030003218A - 트리아자스피로[5.5]운데칸 유도체 및 이들을유효성분으로 하는 약제 - Google Patents
트리아자스피로[5.5]운데칸 유도체 및 이들을유효성분으로 하는 약제 Download PDFInfo
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- KR20030003218A KR20030003218A KR1020027007117A KR20027007117A KR20030003218A KR 20030003218 A KR20030003218 A KR 20030003218A KR 1020027007117 A KR1020027007117 A KR 1020027007117A KR 20027007117 A KR20027007117 A KR 20027007117A KR 20030003218 A KR20030003218 A KR 20030003218A
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- KR
- South Korea
- Prior art keywords
- dioxo
- triazaspiro
- butyl
- undecan
- undecane
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- 229940079593 drug Drugs 0.000 title description 3
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- 102000009410 Chemokine receptor Human genes 0.000 claims abstract description 8
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- -1 Cyc1 Chemical group 0.000 claims description 537
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 134
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- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 69
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 61
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 42
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 35
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- 125000005843 halogen group Chemical group 0.000 claims description 33
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- 125000003342 alkenyl group Chemical group 0.000 claims description 26
- 125000000304 alkynyl group Chemical group 0.000 claims description 26
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- 125000003003 spiro group Chemical group 0.000 claims description 22
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- 125000004122 cyclic group Chemical group 0.000 claims description 17
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- 125000004434 sulfur atom Chemical group 0.000 claims description 17
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
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- NECLQTPQJZSWOE-UHFFFAOYSA-N spiro[5.5]undecane Chemical compound C1CCCCC21CCCCC2 NECLQTPQJZSWOE-UHFFFAOYSA-N 0.000 claims description 11
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 10
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
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- 208000030507 AIDS Diseases 0.000 claims description 5
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- 230000001629 suppression Effects 0.000 claims description 4
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- 230000000172 allergic effect Effects 0.000 claims description 3
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- DWZQMFUERYCBDJ-UHFFFAOYSA-N 1-(furan-2-ylmethyl)-3-(2-methylpropyl)-9-[(4-phenoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C=1C=COC=1CN1C(=O)C(CC(C)C)NC(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=CC=C1 DWZQMFUERYCBDJ-UHFFFAOYSA-N 0.000 claims 1
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- RHBBDGMXECXMIO-SANMLTNESA-N 4-[4-[[(3s)-1-butyl-3-(2-methylpropyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]benzenesulfonamide Chemical compound CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC=2C=CC(OC=3C=CC(=CC=3)S(N)(=O)=O)=CC=2)CC1 RHBBDGMXECXMIO-SANMLTNESA-N 0.000 claims 1
- BTCCUUAGVNACMI-MHZLTWQESA-N 4-[4-[[(3s)-1-butyl-3-(2-methylpropyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]benzonitrile Chemical compound CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC=2C=CC(OC=3C=CC(=CC=3)C#N)=CC=2)CC1 BTCCUUAGVNACMI-MHZLTWQESA-N 0.000 claims 1
- IDVCUTICQWIJRM-PMERELPUSA-N 4-[4-[[(3s)-1-butyl-3-(cyclohexylmethyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]-3,5-dimethylpyrazol-1-yl]-n,n-dimethylbenzenesulfonamide Chemical compound C([C@H]1C(=O)N(C2(CCN(CC3=C(N(N=C3C)C=3C=CC(=CC=3)S(=O)(=O)N(C)C)C)CC2)C(=O)N1)CCCC)C1CCCCC1 IDVCUTICQWIJRM-PMERELPUSA-N 0.000 claims 1
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- HQTUGXJLTJOFDT-PMERELPUSA-N 4-[4-[[(3s)-1-butyl-3-(cyclohexylmethyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]-3,5-dimethylpyrazol-1-yl]-n-(2-hydroxyethyl)benzenesulfonamide Chemical compound C([C@H]1C(=O)N(C2(CCN(CC3=C(N(N=C3C)C=3C=CC(=CC=3)S(=O)(=O)NCCO)C)CC2)C(=O)N1)CCCC)C1CCCCC1 HQTUGXJLTJOFDT-PMERELPUSA-N 0.000 claims 1
- FXPLSANPRQWBKR-YTTGMZPUSA-N 4-[4-[[(3s)-1-butyl-3-(cyclohexylmethyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]-3,5-dimethylpyrazol-1-yl]-n-[2-(dimethylamino)ethyl]benzenesulfonamide Chemical compound C([C@H]1C(=O)N(C2(CCN(CC3=C(N(N=C3C)C=3C=CC(=CC=3)S(=O)(=O)NCCN(C)C)C)CC2)C(=O)N1)CCCC)C1CCCCC1 FXPLSANPRQWBKR-YTTGMZPUSA-N 0.000 claims 1
- PHKIRJUTTIGOCK-LJAQVGFWSA-N 4-[4-[[(3s)-1-butyl-3-(cyclohexylmethyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]-3,5-dimethylpyrazol-1-yl]-n-methylbenzenesulfonamide Chemical compound C([C@H]1C(=O)N(C2(CCN(CC3=C(N(N=C3C)C=3C=CC(=CC=3)S(=O)(=O)NC)C)CC2)C(=O)N1)CCCC)C1CCCCC1 PHKIRJUTTIGOCK-LJAQVGFWSA-N 0.000 claims 1
- CLLOWIQKYBUXAK-NDEPHWFRSA-N 4-[4-[[(3s)-1-butyl-3-(cyclohexylmethyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]-3,5-dimethylpyrazol-1-yl]benzoic acid Chemical compound C([C@H]1C(=O)N(C2(CCN(CC3=C(N(N=C3C)C=3C=CC(=CC=3)C(O)=O)C)CC2)C(=O)N1)CCCC)C1CCCCC1 CLLOWIQKYBUXAK-NDEPHWFRSA-N 0.000 claims 1
- VJCFKVFKQRBGGK-XIFFEERXSA-N 4-[4-[[(3s)-1-butyl-3-(cyclohexylmethyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-n-[2-(dimethylamino)ethyl]benzamide Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=CC(OC=4C=CC(=CC=4)C(=O)NCCN(C)C)=CC=3)CC2)C(=O)N1)CCCC)C1CCCCC1 VJCFKVFKQRBGGK-XIFFEERXSA-N 0.000 claims 1
- XVKXNTWWXVECAF-LJAQVGFWSA-N 4-[4-[[(3s)-1-butyl-3-(cyclohexylmethyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]benzamide Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=CC(OC=4C=CC(=CC=4)C(N)=O)=CC=3)CC2)C(=O)N1)CCCC)C1CCCCC1 XVKXNTWWXVECAF-LJAQVGFWSA-N 0.000 claims 1
- IZRPWEOZEREGKH-LJAQVGFWSA-N 4-[4-[[(3s)-1-butyl-3-(cyclohexylmethyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]benzenesulfonamide Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=CC(OC=4C=CC(=CC=4)S(N)(=O)=O)=CC=3)CC2)C(=O)N1)CCCC)C1CCCCC1 IZRPWEOZEREGKH-LJAQVGFWSA-N 0.000 claims 1
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- BCPKLVNCFNOUST-NDEPHWFRSA-N (3s)-1-[(4-fluorophenyl)methyl]-3-(2-methylpropyl)-9-(6-phenylhexyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N([C@H](C(N1CC=2C=CC(F)=CC=2)=O)CC(C)C)C(=O)C1(CC1)CCN1CCCCCCC1=CC=CC=C1 BCPKLVNCFNOUST-NDEPHWFRSA-N 0.000 description 1
- XJQFIVQDBSCHKG-MHZLTWQESA-N (3s)-1-[(4-methoxyphenyl)methyl]-3-(2-methylpropyl)-9-(4-phenylbutyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C1=CC(OC)=CC=C1CN1C2(CCN(CCCCC=3C=CC=CC=3)CC2)C(=O)N[C@@H](CC(C)C)C1=O XJQFIVQDBSCHKG-MHZLTWQESA-N 0.000 description 1
- PPENIPJQDRNOJB-NDEPHWFRSA-N (3s)-1-[(4-methoxyphenyl)methyl]-3-(2-methylpropyl)-9-(5-phenylpentyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C1=CC(OC)=CC=C1CN1C2(CCN(CCCCCC=3C=CC=CC=3)CC2)C(=O)N[C@@H](CC(C)C)C1=O PPENIPJQDRNOJB-NDEPHWFRSA-N 0.000 description 1
- KRFLFZUYUWSGBA-LJAQVGFWSA-N (3s)-1-[(4-methoxyphenyl)methyl]-3-(2-methylpropyl)-9-(6-phenylhexyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C1=CC(OC)=CC=C1CN1C2(CCN(CCCCCCC=3C=CC=CC=3)CC2)C(=O)N[C@@H](CC(C)C)C1=O KRFLFZUYUWSGBA-LJAQVGFWSA-N 0.000 description 1
- CWRJZBCNRWARIK-MHZLTWQESA-N (3s)-1-[(4-methylphenyl)methyl]-3-(2-methylpropyl)-9-(4-phenylbutyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N([C@H](C(N1CC=2C=CC(C)=CC=2)=O)CC(C)C)C(=O)C1(CC1)CCN1CCCCC1=CC=CC=C1 CWRJZBCNRWARIK-MHZLTWQESA-N 0.000 description 1
- SFAMPZQJPWYROP-NDEPHWFRSA-N (3s)-1-[(4-methylphenyl)methyl]-3-(2-methylpropyl)-9-(5-phenylpentyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N([C@H](C(N1CC=2C=CC(C)=CC=2)=O)CC(C)C)C(=O)C1(CC1)CCN1CCCCCC1=CC=CC=C1 SFAMPZQJPWYROP-NDEPHWFRSA-N 0.000 description 1
- BPUVRFZFURGGEH-LJAQVGFWSA-N (3s)-1-[(4-methylphenyl)methyl]-3-(2-methylpropyl)-9-(6-phenylhexyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N([C@H](C(N1CC=2C=CC(C)=CC=2)=O)CC(C)C)C(=O)C1(CC1)CCN1CCCCCCC1=CC=CC=C1 BPUVRFZFURGGEH-LJAQVGFWSA-N 0.000 description 1
- BSHMTDNXYULAEG-VWLOTQADSA-N (3s)-1-[(5-methylfuran-2-yl)methyl]-3-(2-methylpropyl)-9-(4-phenylbutyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N([C@H](C(N1CC=2OC(C)=CC=2)=O)CC(C)C)C(=O)C1(CC1)CCN1CCCCC1=CC=CC=C1 BSHMTDNXYULAEG-VWLOTQADSA-N 0.000 description 1
- CWKDHTTYGCZKKQ-SANMLTNESA-N (3s)-1-[(5-methylfuran-2-yl)methyl]-3-(2-methylpropyl)-9-(5-phenylpentyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N([C@H](C(N1CC=2OC(C)=CC=2)=O)CC(C)C)C(=O)C1(CC1)CCN1CCCCCC1=CC=CC=C1 CWKDHTTYGCZKKQ-SANMLTNESA-N 0.000 description 1
- OFJYYJCGOFIRJP-MHZLTWQESA-N (3s)-1-[(5-methylfuran-2-yl)methyl]-3-(2-methylpropyl)-9-(6-phenylhexyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N([C@H](C(N1CC=2OC(C)=CC=2)=O)CC(C)C)C(=O)C1(CC1)CCN1CCCCCCC1=CC=CC=C1 OFJYYJCGOFIRJP-MHZLTWQESA-N 0.000 description 1
- WJAANYSQQGAGDE-MHZLTWQESA-N (3s)-1-[2-(cyclohexen-1-yl)ethyl]-3-(2-methylpropyl)-9-(4-phenylbutyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N([C@H](C(N1CCC=2CCCCC=2)=O)CC(C)C)C(=O)C1(CC1)CCN1CCCCC1=CC=CC=C1 WJAANYSQQGAGDE-MHZLTWQESA-N 0.000 description 1
- TWSLSTGWOYKBDF-NDEPHWFRSA-N (3s)-1-[2-(cyclohexen-1-yl)ethyl]-3-(2-methylpropyl)-9-(5-phenylpentyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N([C@H](C(N1CCC=2CCCCC=2)=O)CC(C)C)C(=O)C1(CC1)CCN1CCCCCC1=CC=CC=C1 TWSLSTGWOYKBDF-NDEPHWFRSA-N 0.000 description 1
- KHEMXYXTCQHFAT-LJAQVGFWSA-N (3s)-1-[2-(cyclohexen-1-yl)ethyl]-3-(2-methylpropyl)-9-(6-phenylhexyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N([C@H](C(N1CCC=2CCCCC=2)=O)CC(C)C)C(=O)C1(CC1)CCN1CCCCCCC1=CC=CC=C1 KHEMXYXTCQHFAT-LJAQVGFWSA-N 0.000 description 1
- RFBYOPSEVMQHIF-QHCPKHFHSA-N (3s)-1-[2-(dimethylamino)ethyl]-3-(2-methylpropyl)-9-(4-phenylbutyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CN(C)CCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CCCCC=2C=CC=CC=2)CC1 RFBYOPSEVMQHIF-QHCPKHFHSA-N 0.000 description 1
- LHTMSLOKQKSRLT-DEOSSOPVSA-N (3s)-1-[2-(dimethylamino)ethyl]-3-(2-methylpropyl)-9-(5-phenylpentyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CN(C)CCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CCCCCC=2C=CC=CC=2)CC1 LHTMSLOKQKSRLT-DEOSSOPVSA-N 0.000 description 1
- SIIICDBTTUJYLX-VWLOTQADSA-N (3s)-1-[2-(dimethylamino)ethyl]-3-(2-methylpropyl)-9-(6-phenylhexyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CN(C)CCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CCCCCCC=2C=CC=CC=2)CC1 SIIICDBTTUJYLX-VWLOTQADSA-N 0.000 description 1
- WJOFGXDVBCWOSU-DEOSSOPVSA-N (3s)-1-[3-(dimethylamino)propyl]-3-(2-methylpropyl)-9-(4-phenylbutyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CN(C)CCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CCCCC=2C=CC=CC=2)CC1 WJOFGXDVBCWOSU-DEOSSOPVSA-N 0.000 description 1
- GZBOXLQFTGBBEM-VWLOTQADSA-N (3s)-1-[3-(dimethylamino)propyl]-3-(2-methylpropyl)-9-(5-phenylpentyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CN(C)CCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CCCCCC=2C=CC=CC=2)CC1 GZBOXLQFTGBBEM-VWLOTQADSA-N 0.000 description 1
- GZZSFNGYVKKQMT-SANMLTNESA-N (3s)-1-[3-(dimethylamino)propyl]-3-(2-methylpropyl)-9-(6-phenylhexyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CN(C)CCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CCCCCCC=2C=CC=CC=2)CC1 GZZSFNGYVKKQMT-SANMLTNESA-N 0.000 description 1
- MDDMFUUTCXZSOJ-UNFRKHOWSA-N (3s)-1-[[(1s,4s,5s)-6,6-dimethyl-4-bicyclo[3.1.1]heptanyl]methyl]-3-(2-methylpropyl)-9-(4-phenylbutyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N([C@H](C(N1C[C@@H]2[C@@H]3C[C@@H](C3(C)C)CC2)=O)CC(C)C)C(=O)C1(CC1)CCN1CCCCC1=CC=CC=C1 MDDMFUUTCXZSOJ-UNFRKHOWSA-N 0.000 description 1
- ORXSYCPVKHANLM-VVZGZWEYSA-N (3s)-1-[[(1s,4s,5s)-6,6-dimethyl-4-bicyclo[3.1.1]heptanyl]methyl]-3-(2-methylpropyl)-9-(5-phenylpentyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N([C@H](C(N1C[C@@H]2[C@@H]3C[C@@H](C3(C)C)CC2)=O)CC(C)C)C(=O)C1(CC1)CCN1CCCCCC1=CC=CC=C1 ORXSYCPVKHANLM-VVZGZWEYSA-N 0.000 description 1
- GBSNKSDIKZWIRL-RYTSNQFKSA-N (3s)-1-[[(1s,4s,5s)-6,6-dimethyl-4-bicyclo[3.1.1]heptanyl]methyl]-3-(2-methylpropyl)-9-(6-phenylhexyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N([C@H](C(N1C[C@@H]2[C@@H]3C[C@@H](C3(C)C)CC2)=O)CC(C)C)C(=O)C1(CC1)CCN1CCCCCCC1=CC=CC=C1 GBSNKSDIKZWIRL-RYTSNQFKSA-N 0.000 description 1
- REWZTGAPIAJRRD-SNYZSRNZSA-N (3s)-1-but-2-ynyl-3-(2,2-dimethylpropyl)-9-[(4-phenoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.CC#CCN1C(=O)[C@H](CC(C)(C)C)NC(=O)C11CCN(CC=2C=CC(OC=3C=CC=CC=3)=CC=2)CC1 REWZTGAPIAJRRD-SNYZSRNZSA-N 0.000 description 1
- WRYWBVUGUXAPAZ-NDEPHWFRSA-N (3s)-1-but-2-ynyl-3-(cyclohexylmethyl)-9-[(3,5-dimethyl-1-phenylpyrazol-4-yl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound C([C@H]1C(=O)N(C2(CCN(CC3=C(N(N=C3C)C=3C=CC=CC=3)C)CC2)C(=O)N1)CC#CC)C1CCCCC1 WRYWBVUGUXAPAZ-NDEPHWFRSA-N 0.000 description 1
- CFNBHBMYZAUGNX-GITCGBDTSA-N (3s)-1-butan-2-yl-3-(2-methylpropyl)-9-(5-phenylpentyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCC(C)N1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CCCCCC=2C=CC=CC=2)CC1 CFNBHBMYZAUGNX-GITCGBDTSA-N 0.000 description 1
- IQEUTVCMJZGJAI-ZOWNYOTGSA-N (3s)-1-butyl-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCNCC1 IQEUTVCMJZGJAI-ZOWNYOTGSA-N 0.000 description 1
- UXAMBBJHHKLTIB-SNYZSRNZSA-N (3s)-1-butyl-3-(2-methylpropyl)-9-[(4-phenoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC=2C=CC(OC=3C=CC=CC=3)=CC=2)CC1 UXAMBBJHHKLTIB-SNYZSRNZSA-N 0.000 description 1
- ZQQQRDVVHCWMBI-SNYZSRNZSA-N (3s)-1-butyl-3-(2-methylpropyl)-9-[(4-phenylsulfanylphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC=2C=CC(SC=3C=CC=CC=3)=CC=2)CC1 ZQQQRDVVHCWMBI-SNYZSRNZSA-N 0.000 description 1
- APZPNUUGTMYZMK-BDQAORGHSA-N (3s)-1-butyl-3-(2-methylpropyl)-9-[[4-(trifluoromethoxy)phenyl]methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC=2C=CC(OC(F)(F)F)=CC=2)CC1 APZPNUUGTMYZMK-BDQAORGHSA-N 0.000 description 1
- LRAMPPKCUBOSQB-BQAIUKQQSA-N (3s)-1-butyl-3-(cyclohexylmethyl)-9-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.C([C@H]1C(=O)N(C2(CCN(CC=3C=C4OCCOC4=CC=3)CC2)C(=O)N1)CCCC)C1CCCCC1 LRAMPPKCUBOSQB-BQAIUKQQSA-N 0.000 description 1
- HCXZTEGXDHPCNE-BQAIUKQQSA-N (3s)-1-butyl-3-(hydroxymethyl)-9-[(4-phenoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.CCCCN1C(=O)[C@H](CO)NC(=O)C11CCN(CC=2C=CC(OC=3C=CC=CC=3)=CC=2)CC1 HCXZTEGXDHPCNE-BQAIUKQQSA-N 0.000 description 1
- MNIKGZYFLQZIHV-ZDGKEXRSSA-N (3s)-1-butyl-3-[(1r)-1-hydroxy-2-methylpropyl]-9-[(4-phenoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.CCCCN1C(=O)[C@H]([C@H](O)C(C)C)NC(=O)C11CCN(CC=2C=CC(OC=3C=CC=CC=3)=CC=2)CC1 MNIKGZYFLQZIHV-ZDGKEXRSSA-N 0.000 description 1
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- KERHVLJSWVOHGF-BDQAORGHSA-N (3s)-1-butyl-9-[(2-chlorophenyl)methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC=2C(=CC=CC=2)Cl)CC1 KERHVLJSWVOHGF-BDQAORGHSA-N 0.000 description 1
- HPRHMORTEJVDPP-BDQAORGHSA-N (3s)-1-butyl-9-[(2-fluorophenyl)methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC=2C(=CC=CC=2)F)CC1 HPRHMORTEJVDPP-BDQAORGHSA-N 0.000 description 1
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- IQTYTLMPENWMDL-BDQAORGHSA-N (3s)-1-butyl-9-[(3-chlorophenyl)methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC=2C=C(Cl)C=CC=2)CC1 IQTYTLMPENWMDL-BDQAORGHSA-N 0.000 description 1
- WHGFNAHZBXBYPU-BDQAORGHSA-N (3s)-1-butyl-9-[(3-fluoro-4-methoxyphenyl)methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC=2C=C(F)C(OC)=CC=2)CC1 WHGFNAHZBXBYPU-BDQAORGHSA-N 0.000 description 1
- PIONUWKQDSZBCQ-BDQAORGHSA-N (3s)-1-butyl-9-[(3-fluorophenyl)methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC=2C=C(F)C=CC=2)CC1 PIONUWKQDSZBCQ-BDQAORGHSA-N 0.000 description 1
- IGTOVJVMZWLJCM-FYZYNONXSA-N (3s)-1-butyl-9-[(3-hydroxy-4-methoxyphenyl)methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC=2C=C(O)C(OC)=CC=2)CC1 IGTOVJVMZWLJCM-FYZYNONXSA-N 0.000 description 1
- DFDQCDNMHYJUOV-BOXHHOBZSA-N (3s)-1-butyl-9-[(3-methylphenyl)methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC=2C=C(C)C=CC=2)CC1 DFDQCDNMHYJUOV-BOXHHOBZSA-N 0.000 description 1
- JOTAIIVBOHIXFC-JIDHJSLPSA-N (3s)-1-butyl-9-[(4-butylphenyl)methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC=2C=CC(CCCC)=CC=2)CC1 JOTAIIVBOHIXFC-JIDHJSLPSA-N 0.000 description 1
- KZASBJNSLBUCPI-BDQAORGHSA-N (3s)-1-butyl-9-[(4-chlorophenyl)methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC=2C=CC(Cl)=CC=2)CC1 KZASBJNSLBUCPI-BDQAORGHSA-N 0.000 description 1
- OTJIIAVYIWHBOR-SNYZSRNZSA-N (3s)-1-butyl-9-[(4-cyclohexyloxyphenyl)methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC=2C=CC(OC3CCCCC3)=CC=2)CC1 OTJIIAVYIWHBOR-SNYZSRNZSA-N 0.000 description 1
- IUSSMKBCFNDMIG-BDQAORGHSA-N (3s)-1-butyl-9-[(4-fluorophenyl)methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC=2C=CC(F)=CC=2)CC1 IUSSMKBCFNDMIG-BDQAORGHSA-N 0.000 description 1
- NIZXIWVXLPXITN-BOXHHOBZSA-N (3s)-1-butyl-9-[(4-methylphenyl)methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC=2C=CC(C)=CC=2)CC1 NIZXIWVXLPXITN-BOXHHOBZSA-N 0.000 description 1
- ZFGKLAIULBTJFW-FYZYNONXSA-N (3s)-1-butyl-9-[(7-methoxy-1,3-benzodioxol-5-yl)methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.CCCCN1C(=O)[C@H](CC(C)C)NC(=O)C11CCN(CC=2C=C(OC)C=3OCOC=3C=2)CC1 ZFGKLAIULBTJFW-FYZYNONXSA-N 0.000 description 1
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- FBCJBGUUTIOILL-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-(naphthalen-2-ylmethyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.N1C(=O)C2(CCN(CC=3C=C4C=CC=CC4=CC=3)CC2)N(CCCC)C(=O)C1CC1CCCCC1 FBCJBGUUTIOILL-UHFFFAOYSA-N 0.000 description 1
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- CNUWDXBCMGCXEG-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[(2,4,6-trimethoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.N1C(=O)C2(CCN(CC=3C(=CC(OC)=CC=3OC)OC)CC2)N(CCCC)C(=O)C1CC1CCCCC1 CNUWDXBCMGCXEG-UHFFFAOYSA-N 0.000 description 1
- RKWCPCQSPBZQND-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[(2,4-dioxo-1h-pyrimidin-5-yl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N1C(=O)C2(CCN(CC=3C(NC(=O)NC=3)=O)CC2)N(CCCC)C(=O)C1CC1CCCCC1 RKWCPCQSPBZQND-UHFFFAOYSA-N 0.000 description 1
- JPDJMFSMWPYMRF-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[(2-hydroxy-4-methoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.N1C(=O)C2(CCN(CC=3C(=CC(OC)=CC=3)O)CC2)N(CCCC)C(=O)C1CC1CCCCC1 JPDJMFSMWPYMRF-UHFFFAOYSA-N 0.000 description 1
- GUISUVGHUSIVKO-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[(2-phenyl-1,3-thiazol-4-yl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.N1C(=O)C2(CCN(CC=3N=C(SC=3)C=3C=CC=CC=3)CC2)N(CCCC)C(=O)C1CC1CCCCC1 GUISUVGHUSIVKO-UHFFFAOYSA-N 0.000 description 1
- NXMWMKGIMONOPN-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[(2-phenyl-1h-imidazol-5-yl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;dihydrochloride Chemical compound Cl.Cl.N1C(=O)C2(CCN(CC=3N=C(NC=3)C=3C=CC=CC=3)CC2)N(CCCC)C(=O)C1CC1CCCCC1 NXMWMKGIMONOPN-UHFFFAOYSA-N 0.000 description 1
- KANAPYRASASSJG-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[(3,4-dimethoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.N1C(=O)C2(CCN(CC=3C=C(OC)C(OC)=CC=3)CC2)N(CCCC)C(=O)C1CC1CCCCC1 KANAPYRASASSJG-UHFFFAOYSA-N 0.000 description 1
- NNBWHOPLUVRYKZ-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[(3,5-dimethoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.N1C(=O)C2(CCN(CC=3C=C(OC)C=C(OC)C=3)CC2)N(CCCC)C(=O)C1CC1CCCCC1 NNBWHOPLUVRYKZ-UHFFFAOYSA-N 0.000 description 1
- FYTLIWBMCUJKQN-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[(3,5-dimethyl-1-phenylpyrazol-4-yl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;dihydrochloride Chemical compound Cl.Cl.N1C(=O)C2(CCN(CC3=C(N(N=C3C)C=3C=CC=CC=3)C)CC2)N(CCCC)C(=O)C1CC1CCCCC1 FYTLIWBMCUJKQN-UHFFFAOYSA-N 0.000 description 1
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- ZZVKUONIRFTWOK-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[(4-methyl-1,3-thiazol-2-yl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.N1C(=O)C2(CCN(CC=3SC=C(C)N=3)CC2)N(CCCC)C(=O)C1CC1CCCCC1 ZZVKUONIRFTWOK-UHFFFAOYSA-N 0.000 description 1
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- DYXLSNKGBZBECO-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[(4-nitrophenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.N1C(=O)C2(CCN(CC=3C=CC(=CC=3)[N+]([O-])=O)CC2)N(CCCC)C(=O)C1CC1CCCCC1 DYXLSNKGBZBECO-UHFFFAOYSA-N 0.000 description 1
- PIMBSDCVZVPYEY-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[(4-phenoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.N1C(=O)C2(CCN(CC=3C=CC(OC=4C=CC=CC=4)=CC=3)CC2)N(CCCC)C(=O)C1CC1CCCCC1 PIMBSDCVZVPYEY-UHFFFAOYSA-N 0.000 description 1
- SGHAUWGAUUKKTP-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[(4-phenylmethoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N1C(=O)C2(CCN(CC=3C=CC(OCC=4C=CC=CC=4)=CC=3)CC2)N(CCCC)C(=O)C1CC1CCCCC1 SGHAUWGAUUKKTP-UHFFFAOYSA-N 0.000 description 1
- HLMNDIXSITYHSN-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[(4-propoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.N1C(=O)C2(CCN(CC=3C=CC(OCCC)=CC=3)CC2)N(CCCC)C(=O)C1CC1CCCCC1 HLMNDIXSITYHSN-UHFFFAOYSA-N 0.000 description 1
- PXZWNBZYXMOWPP-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[(5-ethylfuran-2-yl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.N1C(=O)C2(CCN(CC=3OC(CC)=CC=3)CC2)N(CCCC)C(=O)C1CC1CCCCC1 PXZWNBZYXMOWPP-UHFFFAOYSA-N 0.000 description 1
- HYSQHNRIKAMYHP-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[(5-ethylthiophen-2-yl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.N1C(=O)C2(CCN(CC=3SC(CC)=CC=3)CC2)N(CCCC)C(=O)C1CC1CCCCC1 HYSQHNRIKAMYHP-UHFFFAOYSA-N 0.000 description 1
- SGWLZMDNXUYFAY-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[(5-methyl-1,3-thiazol-2-yl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.N1C(=O)C2(CCN(CC=3SC(C)=CN=3)CC2)N(CCCC)C(=O)C1CC1CCCCC1 SGWLZMDNXUYFAY-UHFFFAOYSA-N 0.000 description 1
- ZURNFBLLQSKNFG-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[(6-methoxynaphthalen-2-yl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.N1C(=O)C2(CCN(CC=3C=C4C=CC(OC)=CC4=CC=3)CC2)N(CCCC)C(=O)C1CC1CCCCC1 ZURNFBLLQSKNFG-UHFFFAOYSA-N 0.000 description 1
- BZORTMLNSYIMGW-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[(6-phenoxypyridin-3-yl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;dihydrochloride Chemical compound Cl.Cl.N1C(=O)C2(CCN(CC=3C=NC(OC=4C=CC=CC=4)=CC=3)CC2)N(CCCC)C(=O)C1CC1CCCCC1 BZORTMLNSYIMGW-UHFFFAOYSA-N 0.000 description 1
- KAEAGEXGPWAMOT-GYVLLFFHSA-N 1-butyl-3-(cyclohexylmethyl)-9-[(e)-3-phenylprop-2-enyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.N1C(=O)C2(CCN(C\C=C\C=3C=CC=CC=3)CC2)N(CCCC)C(=O)C1CC1CCCCC1 KAEAGEXGPWAMOT-GYVLLFFHSA-N 0.000 description 1
- XPFBJKFREHANHL-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.N1C(=O)C2(CCN(CC2)C(C)C=2C=C3OCCOC3=CC=2)N(CCCC)C(=O)C1CC1CCCCC1 XPFBJKFREHANHL-UHFFFAOYSA-N 0.000 description 1
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- OAMSCSRZXMYNAB-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[[4-(n-phenylanilino)phenyl]methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.N1C(=O)C2(CCN(CC=3C=CC(=CC=3)N(C=3C=CC=CC=3)C=3C=CC=CC=3)CC2)N(CCCC)C(=O)C1CC1CCCCC1 OAMSCSRZXMYNAB-UHFFFAOYSA-N 0.000 description 1
- ZTVHBYWYRMBEEN-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[[5-(4-methoxyphenyl)thiophen-2-yl]methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N1C(=O)C2(CCN(CC=3SC(=CC=3)C=3C=CC(OC)=CC=3)CC2)N(CCCC)C(=O)C1CC1CCCCC1 ZTVHBYWYRMBEEN-UHFFFAOYSA-N 0.000 description 1
- AKSUYRFQJDKMEX-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[[5-(hydroxymethyl)furan-2-yl]methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N1C(=O)C2(CCN(CC=3OC(CO)=CC=3)CC2)N(CCCC)C(=O)C1CC1CCCCC1 AKSUYRFQJDKMEX-UHFFFAOYSA-N 0.000 description 1
- ZJUIGYNXOWZXMU-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[[5-[2,6-dichloro-4-(trifluoromethyl)phenyl]furan-2-yl]methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N1C(=O)C2(CCN(CC=3OC(=CC=3)C=3C(=CC(=CC=3Cl)C(F)(F)F)Cl)CC2)N(CCCC)C(=O)C1CC1CCCCC1 ZJUIGYNXOWZXMU-UHFFFAOYSA-N 0.000 description 1
- ICXXDJZAPVGJSB-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[[5-[2-(trifluoromethoxy)phenyl]furan-2-yl]methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N1C(=O)C2(CCN(CC=3OC(=CC=3)C=3C(=CC=CC=3)OC(F)(F)F)CC2)N(CCCC)C(=O)C1CC1CCCCC1 ICXXDJZAPVGJSB-UHFFFAOYSA-N 0.000 description 1
- DLCJJLLWTBGGON-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[[5-[2-(trifluoromethyl)phenyl]furan-2-yl]methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)C(NC(=O)C12CCN(CC2)CC3=CC=C(O3)C4=CC=CC=C4C(F)(F)F)CC5CCCCC5 DLCJJLLWTBGGON-UHFFFAOYSA-N 0.000 description 1
- GYJLRRVOGLDEET-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-[[5-[3-(trifluoromethyl)phenyl]furan-2-yl]methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N1C(=O)C2(CCN(CC=3OC(=CC=3)C=3C=C(C=CC=3)C(F)(F)F)CC2)N(CCCC)C(=O)C1CC1CCCCC1 GYJLRRVOGLDEET-UHFFFAOYSA-N 0.000 description 1
- LXZPCIALXXGCRT-UHFFFAOYSA-N 1-butyl-3-(cyclopentylmethyl)-9-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.N1C(=O)C2(CCN(CC=3C=C4OCCOC4=CC=3)CC2)N(CCCC)C(=O)C1CC1CCCC1 LXZPCIALXXGCRT-UHFFFAOYSA-N 0.000 description 1
- VBQZJQDFCYXMQX-UHFFFAOYSA-N 1-butyl-3-(cyclopentylmethyl)-9-[(4-phenoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.N1C(=O)C2(CCN(CC=3C=CC(OC=4C=CC=CC=4)=CC=3)CC2)N(CCCC)C(=O)C1CC1CCCC1 VBQZJQDFCYXMQX-UHFFFAOYSA-N 0.000 description 1
- XQTMOOACTBCYJU-UHFFFAOYSA-N 1-butyl-3-(methoxymethyl)-9-[(4-phenoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.CCCCN1C(=O)C(COC)NC(=O)C11CCN(CC=2C=CC(OC=3C=CC=CC=3)=CC=2)CC1 XQTMOOACTBCYJU-UHFFFAOYSA-N 0.000 description 1
- UTLKCXLONHYZPP-DEOSSOPVSA-N 1-butyl-3-[4-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]urea Chemical compound CCCN1C(=O)[C@H](CCCCNC(=O)NCCCC)NC(=O)C11CCN(CCC=2C=CC=CC=2)CC1 UTLKCXLONHYZPP-DEOSSOPVSA-N 0.000 description 1
- KAFXCXGMNHARKK-UHFFFAOYSA-N 1-butyl-9-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.CCCCN1C(=O)C(CC(C)C)NC(=O)C11CCN(CC=2C=C3OCCOC3=CC=2)CC1 KAFXCXGMNHARKK-UHFFFAOYSA-N 0.000 description 1
- SOQQNXBWMLEGDC-UHFFFAOYSA-N 1-butyl-9-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-3-(oxan-4-ylmethyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.N1C(=O)C2(CCN(CC=3C=C4OCCOC4=CC=3)CC2)N(CCCC)C(=O)C1CC1CCOCC1 SOQQNXBWMLEGDC-UHFFFAOYSA-N 0.000 description 1
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- VTFLLHNRMFKNGY-UHFFFAOYSA-N 1-butyl-9-[(1-methylindol-3-yl)methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)C(CC(C)C)NC(=O)C11CCN(CC=2C3=CC=CC=C3N(C)C=2)CC1 VTFLLHNRMFKNGY-UHFFFAOYSA-N 0.000 description 1
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- OZRLYPRTVUJHSS-UHFFFAOYSA-N 1-butyl-9-[(4-cyclopentyloxyphenyl)methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.CCCCN1C(=O)C(CC(C)C)NC(=O)C11CCN(CC=2C=CC(OC3CCCC3)=CC=2)CC1 OZRLYPRTVUJHSS-UHFFFAOYSA-N 0.000 description 1
- MJJSJKSKZNPIIV-UHFFFAOYSA-N 1-butyl-9-[(4-phenoxyphenyl)methyl]-3-propyl-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride Chemical compound Cl.CCCCN1C(=O)C(CCC)NC(=O)C11CCN(CC=2C=CC(OC=3C=CC=CC=3)=CC=2)CC1 MJJSJKSKZNPIIV-UHFFFAOYSA-N 0.000 description 1
- VGTQHVIIMHKNLI-UHFFFAOYSA-N 1-butyl-9-[(5-chloro-3-methyl-1-phenylpyrazol-4-yl)methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)C(CC(C)C)NC(=O)C11CCN(CC2=C(N(N=C2C)C=2C=CC=CC=2)Cl)CC1 VGTQHVIIMHKNLI-UHFFFAOYSA-N 0.000 description 1
- NPUQYRDIWLXIFE-UHFFFAOYSA-N 1-butyl-9-[(5-chloro-3-methyl-1-phenylpyrazol-4-yl)methyl]-3-(cyclohexylmethyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N1C(=O)C2(CCN(CC3=C(N(N=C3C)C=3C=CC=CC=3)Cl)CC2)N(CCCC)C(=O)C1CC1CCCCC1 NPUQYRDIWLXIFE-UHFFFAOYSA-N 0.000 description 1
- PKQKFKWTCPPEQR-UHFFFAOYSA-N 1-butyl-9-[(5-ethylfuran-2-yl)methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)C(CC(C)C)NC(=O)C11CCN(CC=2OC(CC)=CC=2)CC1 PKQKFKWTCPPEQR-UHFFFAOYSA-N 0.000 description 1
- SWBRKLRSDMWXHA-UHFFFAOYSA-N 1-butyl-9-[(5-ethylthiophen-2-yl)methyl]-3-(2-methylpropyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound CCCCN1C(=O)C(CC(C)C)NC(=O)C11CCN(CC=2SC(CC)=CC=2)CC1 SWBRKLRSDMWXHA-UHFFFAOYSA-N 0.000 description 1
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- QHNZATYWHWGWLP-LJAQVGFWSA-N benzyl n-[3-[(3s)-1-(3-imidazol-1-ylpropyl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound N([C@H](C(N1CCCN2C=NC=C2)=O)CCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 QHNZATYWHWGWLP-LJAQVGFWSA-N 0.000 description 1
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- AGBNASCYOOHZGZ-NDEPHWFRSA-N benzyl n-[3-[(3s)-1-(3-methylbutyl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CCC(C)C)CCNC(=O)OCC1=CC=CC=C1 AGBNASCYOOHZGZ-NDEPHWFRSA-N 0.000 description 1
- RBNMXMSXPLHOMQ-MHZLTWQESA-N benzyl n-[3-[(3s)-1-(3-methylsulfanylpropyl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CCCSC)CCNC(=O)OCC1=CC=CC=C1 RBNMXMSXPLHOMQ-MHZLTWQESA-N 0.000 description 1
- RUWSHCXHKFOOTE-PMERELPUSA-N benzyl n-[3-[(3s)-1-(3-morpholin-4-ylpropyl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound N([C@H](C(N1CCCN2CCOCC2)=O)CCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 RUWSHCXHKFOOTE-PMERELPUSA-N 0.000 description 1
- KPFYGTPHVRPRQG-BTMGADRYSA-N benzyl n-[3-[(3s)-1-(4-methylpentan-2-yl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)C(C)CC(C)C)CCNC(=O)OCC1=CC=CC=C1 KPFYGTPHVRPRQG-BTMGADRYSA-N 0.000 description 1
- CYKUUAGYFZLHLN-PMERELPUSA-N benzyl n-[3-[(3s)-1-(cyclohexylmethyl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound N([C@H](C(N1CC2CCCCC2)=O)CCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 CYKUUAGYFZLHLN-PMERELPUSA-N 0.000 description 1
- VNFXWJYATGHQPL-MHZLTWQESA-N benzyl n-[3-[(3s)-1-(cyclopropylmethyl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound N([C@H](C(N1CC2CC2)=O)CCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 VNFXWJYATGHQPL-MHZLTWQESA-N 0.000 description 1
- OMSAANMVQWLQGR-ZSXSBBPPSA-N benzyl n-[3-[(3s)-1-[(1-ethylpyrrolidin-2-yl)methyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound CCN1CCCC1CN1C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N[C@@H](CCCNC(=O)OCC=2C=CC=CC=2)C1=O OMSAANMVQWLQGR-ZSXSBBPPSA-N 0.000 description 1
- YAXDTEOQGUYBND-NSJVFKKDSA-N benzyl n-[3-[(3s)-1-[(1r)-1-(4-methylphenyl)ethyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)[C@H](C)C=1C=CC(C)=CC=1)CCNC(=O)OCC1=CC=CC=C1 YAXDTEOQGUYBND-NSJVFKKDSA-N 0.000 description 1
- ISNUVMWTPCWYRJ-PMERELPUSA-N benzyl n-[3-[(3s)-1-[(2-fluorophenyl)methyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound FC1=CC=CC=C1CN1C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N[C@@H](CCCNC(=O)OCC=2C=CC=CC=2)C1=O ISNUVMWTPCWYRJ-PMERELPUSA-N 0.000 description 1
- FFTNVDPUUIWIKJ-PMERELPUSA-N benzyl n-[3-[(3s)-1-[(2-methoxyphenyl)methyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound COC1=CC=CC=C1CN1C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N[C@@H](CCCNC(=O)OCC=2C=CC=CC=2)C1=O FFTNVDPUUIWIKJ-PMERELPUSA-N 0.000 description 1
- XMAFKVBXNXYRFU-OZXSUGGESA-N benzyl n-[3-[(3s)-1-[(2s)-2-hydroxypropyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)C[C@@H](O)C)CCNC(=O)OCC1=CC=CC=C1 XMAFKVBXNXYRFU-OZXSUGGESA-N 0.000 description 1
- HMZQGTDWBLVYRF-PMERELPUSA-N benzyl n-[3-[(3s)-1-[(3-chlorophenyl)methyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound ClC1=CC=CC(CN2C3(CCN(CCC=4C=CC=CC=4)CC3)C(=O)N[C@@H](CCCNC(=O)OCC=3C=CC=CC=3)C2=O)=C1 HMZQGTDWBLVYRF-PMERELPUSA-N 0.000 description 1
- HTMPAPWKWAWPKO-PMERELPUSA-N benzyl n-[3-[(3s)-1-[(3-fluorophenyl)methyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound FC1=CC=CC(CN2C3(CCN(CCC=4C=CC=CC=4)CC3)C(=O)N[C@@H](CCCNC(=O)OCC=3C=CC=CC=3)C2=O)=C1 HTMPAPWKWAWPKO-PMERELPUSA-N 0.000 description 1
- WPLRVSXHEFAYKN-HKBQPEDESA-N benzyl n-[3-[(3s)-1-[(3-methoxyphenyl)methyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound COC1=CC=CC(CN2C3(CCN(CCC=4C=CC=CC=4)CC3)C(=O)N[C@@H](CCCNC(=O)OCC=3C=CC=CC=3)C2=O)=C1 WPLRVSXHEFAYKN-HKBQPEDESA-N 0.000 description 1
- UOAFIDJEFLRLGP-PMERELPUSA-N benzyl n-[3-[(3s)-1-[(4-fluorophenyl)methyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound C1=CC(F)=CC=C1CN1C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N[C@@H](CCCNC(=O)OCC=2C=CC=CC=2)C1=O UOAFIDJEFLRLGP-PMERELPUSA-N 0.000 description 1
- PKEBMNFAQAQEAJ-HKBQPEDESA-N benzyl n-[3-[(3s)-1-[(4-methoxyphenyl)methyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound C1=CC(OC)=CC=C1CN1C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N[C@@H](CCCNC(=O)OCC=2C=CC=CC=2)C1=O PKEBMNFAQAQEAJ-HKBQPEDESA-N 0.000 description 1
- IRVOJQBSFRUTMF-HKBQPEDESA-N benzyl n-[3-[(3s)-1-[(4-methylphenyl)methyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound C1=CC(C)=CC=C1CN1C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N[C@@H](CCCNC(=O)OCC=2C=CC=CC=2)C1=O IRVOJQBSFRUTMF-HKBQPEDESA-N 0.000 description 1
- GSTLAKQICYGKGI-LJAQVGFWSA-N benzyl n-[3-[(3s)-1-[(5-methylfuran-2-yl)methyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound O1C(C)=CC=C1CN1C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N[C@@H](CCCNC(=O)OCC=2C=CC=CC=2)C1=O GSTLAKQICYGKGI-LJAQVGFWSA-N 0.000 description 1
- NDYXTMIFMOXKJF-ZSXSBBPPSA-N benzyl n-[3-[(3s)-1-[2-(1-methylpyrrolidin-2-yl)ethyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound CN1CCCC1CCN1C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N[C@@H](CCCNC(=O)OCC=2C=CC=CC=2)C1=O NDYXTMIFMOXKJF-ZSXSBBPPSA-N 0.000 description 1
- UXKZDPSYPBYVOF-HKBQPEDESA-N benzyl n-[3-[(3s)-1-[2-(cyclohexen-1-yl)ethyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound N([C@H](C(N1CCC=2CCCCC=2)=O)CCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 UXKZDPSYPBYVOF-HKBQPEDESA-N 0.000 description 1
- RJYLITUYQRGJIK-MHZLTWQESA-N benzyl n-[3-[(3s)-1-[2-(dimethylamino)ethyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CCN(C)C)CCNC(=O)OCC1=CC=CC=C1 RJYLITUYQRGJIK-MHZLTWQESA-N 0.000 description 1
- HYORZJXFBXLQGD-UMSFTDKQSA-N benzyl n-[3-[(3s)-1-[2-(n-ethyl-3-methylanilino)ethyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CCN(CC)C=1C=C(C)C=CC=1)CCNC(=O)OCC1=CC=CC=C1 HYORZJXFBXLQGD-UMSFTDKQSA-N 0.000 description 1
- ADZXCPHPNSFWFX-NDEPHWFRSA-N benzyl n-[3-[(3s)-1-[3-(dimethylamino)propyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CCCN(C)C)CCNC(=O)OCC1=CC=CC=C1 ADZXCPHPNSFWFX-NDEPHWFRSA-N 0.000 description 1
- AZEPZIJGLPTBFD-ZLESDFJESA-N benzyl n-[3-[(3s)-1-[[(1s,4s,5s)-6,6-dimethyl-4-bicyclo[3.1.1]heptanyl]methyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)C[C@@H]1[C@@H]2C[C@H](CC1)C2(C)C)CCNC(=O)OCC1=CC=CC=C1 AZEPZIJGLPTBFD-ZLESDFJESA-N 0.000 description 1
- KWRUZGTZNPMKJM-PMERELPUSA-N benzyl n-[3-[(3s)-1-benzyl-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound N([C@H](C(N1CC=2C=CC=CC=2)=O)CCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 KWRUZGTZNPMKJM-PMERELPUSA-N 0.000 description 1
- OMEJQRLCXCBPQT-WKDCXCOVSA-N benzyl n-[3-[(3s)-1-butan-2-yl-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)C(C)CC)CCNC(=O)OCC1=CC=CC=C1 OMEJQRLCXCBPQT-WKDCXCOVSA-N 0.000 description 1
- GSVFKIFWCTTYLC-MHZLTWQESA-N benzyl n-[3-[(3s)-1-butyl-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CCCC)CCNC(=O)OCC1=CC=CC=C1 GSVFKIFWCTTYLC-MHZLTWQESA-N 0.000 description 1
- WKHRADDYCGCWSY-MHZLTWQESA-N benzyl n-[3-[(3s)-1-cyclobutyl-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound N([C@H](C(N1C2CCC2)=O)CCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 WKHRADDYCGCWSY-MHZLTWQESA-N 0.000 description 1
- ASFUAJDTGZWGAT-PMERELPUSA-N benzyl n-[3-[(3s)-1-cycloheptyl-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound N([C@H](C(N1C2CCCCCC2)=O)CCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 ASFUAJDTGZWGAT-PMERELPUSA-N 0.000 description 1
- MDQNENRYVVPLTF-LJAQVGFWSA-N benzyl n-[3-[(3s)-1-cyclohexyl-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound N([C@H](C(N1C2CCCCC2)=O)CCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 MDQNENRYVVPLTF-LJAQVGFWSA-N 0.000 description 1
- ZSJRSDDAZQXBPS-HKBQPEDESA-N benzyl n-[3-[(3s)-1-cyclooctyl-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound N([C@H](C(N1C2CCCCCCC2)=O)CCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 ZSJRSDDAZQXBPS-HKBQPEDESA-N 0.000 description 1
- FDYAEPRNDFMHDG-NDEPHWFRSA-N benzyl n-[3-[(3s)-1-cyclopentyl-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound N([C@H](C(N1C2CCCC2)=O)CCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 FDYAEPRNDFMHDG-NDEPHWFRSA-N 0.000 description 1
- VMCQHYTVLFQMIR-SANMLTNESA-N benzyl n-[3-[(3s)-1-cyclopropyl-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound N([C@H](C(N1C2CC2)=O)CCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 VMCQHYTVLFQMIR-SANMLTNESA-N 0.000 description 1
- KYCIIWAZHWLKJH-VWLOTQADSA-N benzyl n-[3-[(3s)-1-ethyl-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CC)CCNC(=O)OCC1=CC=CC=C1 KYCIIWAZHWLKJH-VWLOTQADSA-N 0.000 description 1
- NVQIKBOHRIIWIY-BDTAHNRFSA-N benzyl n-[3-[(3s)-2,5-dioxo-1-(1-phenylethyl)-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)C(C)C=1C=CC=CC=1)CCNC(=O)OCC1=CC=CC=C1 NVQIKBOHRIIWIY-BDTAHNRFSA-N 0.000 description 1
- SRURRGZANWNJIS-CJEZNJPTSA-N benzyl n-[3-[(3s)-2,5-dioxo-1-(4-phenylbutan-2-yl)-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound N([C@@H](CCCNC(=O)OCC=1C=CC=CC=1)C1=O)C(=O)C2(CCN(CCC=3C=CC=CC=3)CC2)N1C(C)CCC1=CC=CC=C1 SRURRGZANWNJIS-CJEZNJPTSA-N 0.000 description 1
- QROXNPPTXRDHDZ-XIFFEERXSA-N benzyl n-[3-[(3s)-2,5-dioxo-1-(4-phenylbutyl)-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound N([C@H](C(N1CCCCC=2C=CC=CC=2)=O)CCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 QROXNPPTXRDHDZ-XIFFEERXSA-N 0.000 description 1
- MYTLDCZVTBLAGK-NMXAJACMSA-N benzyl n-[3-[(3s)-2,5-dioxo-1-pentan-2-yl-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)C(C)CCC)CCNC(=O)OCC1=CC=CC=C1 MYTLDCZVTBLAGK-NMXAJACMSA-N 0.000 description 1
- YXZKWYIFITVFEN-NDEPHWFRSA-N benzyl n-[3-[(3s)-2,5-dioxo-1-pentan-3-yl-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)C(CC)CC)CCNC(=O)OCC1=CC=CC=C1 YXZKWYIFITVFEN-NDEPHWFRSA-N 0.000 description 1
- ZPWPRKOIKBLPNF-NDEPHWFRSA-N benzyl n-[3-[(3s)-2,5-dioxo-1-pentyl-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CCCCC)CCNC(=O)OCC1=CC=CC=C1 ZPWPRKOIKBLPNF-NDEPHWFRSA-N 0.000 description 1
- SYVMXUCCYHFXPU-LJAQVGFWSA-N benzyl n-[3-[(3s)-2,5-dioxo-1-phenyl-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound N([C@H](C(N1C=2C=CC=CC=2)=O)CCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 SYVMXUCCYHFXPU-LJAQVGFWSA-N 0.000 description 1
- KVTUXJBYUNOBSD-YYMSGCCCSA-N benzyl n-[3-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-(2-phenylpropyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CC(C)C=1C=CC=CC=1)CCNC(=O)OCC1=CC=CC=C1 KVTUXJBYUNOBSD-YYMSGCCCSA-N 0.000 description 1
- QEUXIYKSSAOQDJ-PMERELPUSA-N benzyl n-[3-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-(2-piperidin-1-ylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound N([C@H](C(N1CCN2CCCCC2)=O)CCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 QEUXIYKSSAOQDJ-PMERELPUSA-N 0.000 description 1
- MRMUCUQNHIITHV-PMERELPUSA-N benzyl n-[3-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-(2-pyridin-2-ylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound N([C@H](C(N1CCC=2N=CC=CC=2)=O)CCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 MRMUCUQNHIITHV-PMERELPUSA-N 0.000 description 1
- PYJVMZYBGNXIBN-PMERELPUSA-N benzyl n-[3-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-(2-pyridin-3-ylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound N([C@H](C(N1CCC=2C=NC=CC=2)=O)CCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 PYJVMZYBGNXIBN-PMERELPUSA-N 0.000 description 1
- GCYGQVSRXQLQSN-PMERELPUSA-N benzyl n-[3-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-(2-pyridin-4-ylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound N([C@H](C(N1CCC=2C=CN=CC=2)=O)CCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 GCYGQVSRXQLQSN-PMERELPUSA-N 0.000 description 1
- ZUIXKTZFFWYCLP-LJAQVGFWSA-N benzyl n-[3-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-(2-thiophen-2-ylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound N([C@H](C(N1CCC=2SC=CC=2)=O)CCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 ZUIXKTZFFWYCLP-LJAQVGFWSA-N 0.000 description 1
- NGPFIXCFAGCBDA-YTTGMZPUSA-N benzyl n-[3-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-(3-phenylpropyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound N([C@H](C(N1CCCC=2C=CC=CC=2)=O)CCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 NGPFIXCFAGCBDA-YTTGMZPUSA-N 0.000 description 1
- DGKGLKHFRLNJOB-LJAQVGFWSA-N benzyl n-[3-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-(pyridin-3-ylmethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound N([C@H](C(N1CC=2C=NC=CC=2)=O)CCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 DGKGLKHFRLNJOB-LJAQVGFWSA-N 0.000 description 1
- DUIFOTVXZSAZOJ-LJAQVGFWSA-N benzyl n-[3-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-(pyridin-4-ylmethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound N([C@H](C(N1CC=2C=CN=CC=2)=O)CCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 DUIFOTVXZSAZOJ-LJAQVGFWSA-N 0.000 description 1
- BSBNQQKKQOIFGK-NDEPHWFRSA-N benzyl n-[3-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-(thiophen-2-ylmethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound N([C@H](C(N1CC=2SC=CC=2)=O)CCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 BSBNQQKKQOIFGK-NDEPHWFRSA-N 0.000 description 1
- DWTGELCSFZMZEW-SANMLTNESA-N benzyl n-[3-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-prop-2-enyl-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CC=C)CCNC(=O)OCC1=CC=CC=C1 DWTGELCSFZMZEW-SANMLTNESA-N 0.000 description 1
- WYQHIKQCIIGARS-SANMLTNESA-N benzyl n-[3-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-prop-2-ynyl-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound N([C@H](C(N1CC#C)=O)CCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 WYQHIKQCIIGARS-SANMLTNESA-N 0.000 description 1
- OWJJAWPYRSSSHW-SANMLTNESA-N benzyl n-[3-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-propan-2-yl-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)C(C)C)CCNC(=O)OCC1=CC=CC=C1 OWJJAWPYRSSSHW-SANMLTNESA-N 0.000 description 1
- MWVHYCYYPOXRHI-PMERELPUSA-N benzyl n-[3-[(3s)-2,5-dioxo-9-(6-phenylhexyl)-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]propyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCCCCCC=3C=CC=CC=3)CC2)C(=O)N1)CCC)CCNC(=O)OCC1=CC=CC=C1 MWVHYCYYPOXRHI-PMERELPUSA-N 0.000 description 1
- OTVGZZSTMBPKPH-UHFFFAOYSA-N benzyl n-[4-(1,9-dibenzyl-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-3-yl)butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CC=2C=CC=CC=2)=O)NC(=O)C1(CC1)CCN1CC1=CC=CC=C1 OTVGZZSTMBPKPH-UHFFFAOYSA-N 0.000 description 1
- YLXZSZMLBMXZIR-UHFFFAOYSA-N benzyl n-[4-(1-benzyl-2,5-dioxo-9-phenyl-1,4,9-triazaspiro[5.5]undecan-3-yl)butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CC=2C=CC=CC=2)=O)NC(=O)C1(CC1)CCN1C1=CC=CC=C1 YLXZSZMLBMXZIR-UHFFFAOYSA-N 0.000 description 1
- SRGSJSWOTMYMDT-UHFFFAOYSA-N benzyl n-[4-(1-benzyl-9-methyl-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-3-yl)butyl]carbamate Chemical compound C1CN(C)CCC21C(=O)NC(CCCCNC(=O)OCC=1C=CC=CC=1)C(=O)N2CC1=CC=CC=C1 SRGSJSWOTMYMDT-UHFFFAOYSA-N 0.000 description 1
- ASZIARGODFGCED-UHFFFAOYSA-N benzyl n-[4-(2,5-dioxo-9-phenyl-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl)butyl]carbamate Chemical compound N1C(=O)C2(CCN(CC2)C=2C=CC=CC=2)N(CCC)C(=O)C1CCCCNC(=O)OCC1=CC=CC=C1 ASZIARGODFGCED-UHFFFAOYSA-N 0.000 description 1
- KZPLUXWZJZRMOT-UHFFFAOYSA-N benzyl n-[4-(9-benzyl-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl)butyl]carbamate Chemical compound N1C(=O)C2(CCN(CC=3C=CC=CC=3)CC2)N(CCC)C(=O)C1CCCCNC(=O)OCC1=CC=CC=C1 KZPLUXWZJZRMOT-UHFFFAOYSA-N 0.000 description 1
- XCIWJOMKDYOBPS-UHFFFAOYSA-N benzyl n-[4-(9-methyl-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl)butyl]carbamate Chemical compound N1C(=O)C2(CCN(C)CC2)N(CCC)C(=O)C1CCCCNC(=O)OCC1=CC=CC=C1 XCIWJOMKDYOBPS-UHFFFAOYSA-N 0.000 description 1
- QVOORWZNVSALRI-WJOKGBTCSA-N benzyl n-[4-[(3r)-2,5-dioxo-9-(6-phenylhexyl)-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@@H]1C(=O)N(C2(CCN(CCCCCCC=3C=CC=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 QVOORWZNVSALRI-WJOKGBTCSA-N 0.000 description 1
- OEJGQKGFOKKMST-NDEPHWFRSA-N benzyl n-[4-[(3s)-1-(2,2-dimethylpropyl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CC(C)(C)C)CCCNC(=O)OCC1=CC=CC=C1 OEJGQKGFOKKMST-NDEPHWFRSA-N 0.000 description 1
- CWRBIOQGKPKAOW-XIFFEERXSA-N benzyl n-[4-[(3s)-1-(2,3-dihydro-1h-inden-5-yl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N([C@H](C(N1C=2C=C3CCCC3=CC=2)=O)CCCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 CWRBIOQGKPKAOW-XIFFEERXSA-N 0.000 description 1
- WTUJPAFLZRSASK-MHZLTWQESA-N benzyl n-[4-[(3s)-1-(2-methoxyethyl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CCOC)CCCNC(=O)OCC1=CC=CC=C1 WTUJPAFLZRSASK-MHZLTWQESA-N 0.000 description 1
- NYAFOILOLYWJHZ-BTMGADRYSA-N benzyl n-[4-[(3s)-1-(2-methylbutyl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CC(C)CC)CCCNC(=O)OCC1=CC=CC=C1 NYAFOILOLYWJHZ-BTMGADRYSA-N 0.000 description 1
- SIMBDXOJYIZAAG-NDEPHWFRSA-N benzyl n-[4-[(3s)-1-(2-methylpropyl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CC(C)C)CCCNC(=O)OCC1=CC=CC=C1 SIMBDXOJYIZAAG-NDEPHWFRSA-N 0.000 description 1
- YRBVGKYIAKQTGY-PMERELPUSA-N benzyl n-[4-[(3s)-1-(2-morpholin-4-ylethyl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N([C@H](C(N1CCN2CCOCC2)=O)CCCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 YRBVGKYIAKQTGY-PMERELPUSA-N 0.000 description 1
- KIQXDHZBMXFYGK-LJAQVGFWSA-N benzyl n-[4-[(3s)-1-(2-tert-butylsulfanylethyl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CCSC(C)(C)C)CCCNC(=O)OCC1=CC=CC=C1 KIQXDHZBMXFYGK-LJAQVGFWSA-N 0.000 description 1
- UFWTZVUXZIMSJM-LJAQVGFWSA-N benzyl n-[4-[(3s)-1-(3-ethoxypropyl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CCCOCC)CCCNC(=O)OCC1=CC=CC=C1 UFWTZVUXZIMSJM-LJAQVGFWSA-N 0.000 description 1
- BUQPZZWDAKAGBP-MHZLTWQESA-N benzyl n-[4-[(3s)-1-(3-hydroxypropyl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CCCO)CCCNC(=O)OCC1=CC=CC=C1 BUQPZZWDAKAGBP-MHZLTWQESA-N 0.000 description 1
- GDINRYSAHIODPH-PMERELPUSA-N benzyl n-[4-[(3s)-1-(3-imidazol-1-ylpropyl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N([C@H](C(N1CCCN2C=NC=C2)=O)CCCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 GDINRYSAHIODPH-PMERELPUSA-N 0.000 description 1
- HAPURUJOPUUUHU-NDEPHWFRSA-N benzyl n-[4-[(3s)-1-(3-methoxypropyl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CCCOC)CCCNC(=O)OCC1=CC=CC=C1 HAPURUJOPUUUHU-NDEPHWFRSA-N 0.000 description 1
- MOWRVYDPJAFAIJ-LJAQVGFWSA-N benzyl n-[4-[(3s)-1-(3-methylbutyl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CCC(C)C)CCCNC(=O)OCC1=CC=CC=C1 MOWRVYDPJAFAIJ-LJAQVGFWSA-N 0.000 description 1
- UFAOQQNWYFYYAV-NDEPHWFRSA-N benzyl n-[4-[(3s)-1-(3-methylsulfanylpropyl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CCCSC)CCCNC(=O)OCC1=CC=CC=C1 UFAOQQNWYFYYAV-NDEPHWFRSA-N 0.000 description 1
- YRYSENOXDVERHL-HKBQPEDESA-N benzyl n-[4-[(3s)-1-(3-morpholin-4-ylpropyl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N([C@H](C(N1CCCN2CCOCC2)=O)CCCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 YRYSENOXDVERHL-HKBQPEDESA-N 0.000 description 1
- SUXHRKXASSMUGA-MILIPEGGSA-N benzyl n-[4-[(3s)-1-(4-methylpentan-2-yl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)C(C)CC(C)C)CCCNC(=O)OCC1=CC=CC=C1 SUXHRKXASSMUGA-MILIPEGGSA-N 0.000 description 1
- ZPSXBMRLIGKTMR-HKBQPEDESA-N benzyl n-[4-[(3s)-1-(cyclohexylmethyl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N([C@H](C(N1CC2CCCCC2)=O)CCCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 ZPSXBMRLIGKTMR-HKBQPEDESA-N 0.000 description 1
- VHCVDWGGCKSHHR-NDEPHWFRSA-N benzyl n-[4-[(3s)-1-(cyclopropylmethyl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N([C@H](C(N1CC2CC2)=O)CCCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 VHCVDWGGCKSHHR-NDEPHWFRSA-N 0.000 description 1
- LGYGYFXNFSAFQO-FLDQDSGZSA-N benzyl n-[4-[(3s)-1-[(1-ethylpyrrolidin-2-yl)methyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound CCN1CCCC1CN1C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N[C@@H](CCCCNC(=O)OCC=2C=CC=CC=2)C1=O LGYGYFXNFSAFQO-FLDQDSGZSA-N 0.000 description 1
- HNESNYXHBCQDDG-HKBQPEDESA-N benzyl n-[4-[(3s)-1-[(2-fluorophenyl)methyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound FC1=CC=CC=C1CN1C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N[C@@H](CCCCNC(=O)OCC=2C=CC=CC=2)C1=O HNESNYXHBCQDDG-HKBQPEDESA-N 0.000 description 1
- IAIIOAQWCZJXOL-HKBQPEDESA-N benzyl n-[4-[(3s)-1-[(2-methoxyphenyl)methyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound COC1=CC=CC=C1CN1C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N[C@@H](CCCCNC(=O)OCC=2C=CC=CC=2)C1=O IAIIOAQWCZJXOL-HKBQPEDESA-N 0.000 description 1
- IUTSVEOBGJUZEA-HKBQPEDESA-N benzyl n-[4-[(3s)-1-[(3-chlorophenyl)methyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound ClC1=CC=CC(CN2C3(CCN(CCC=4C=CC=CC=4)CC3)C(=O)N[C@@H](CCCCNC(=O)OCC=3C=CC=CC=3)C2=O)=C1 IUTSVEOBGJUZEA-HKBQPEDESA-N 0.000 description 1
- FAPVZDAITPSQPB-HKBQPEDESA-N benzyl n-[4-[(3s)-1-[(3-fluorophenyl)methyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound FC1=CC=CC(CN2C3(CCN(CCC=4C=CC=CC=4)CC3)C(=O)N[C@@H](CCCCNC(=O)OCC=3C=CC=CC=3)C2=O)=C1 FAPVZDAITPSQPB-HKBQPEDESA-N 0.000 description 1
- WWLZNEZZFLXWAU-YTTGMZPUSA-N benzyl n-[4-[(3s)-1-[(3-methoxyphenyl)methyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound COC1=CC=CC(CN2C3(CCN(CCC=4C=CC=CC=4)CC3)C(=O)N[C@@H](CCCCNC(=O)OCC=3C=CC=CC=3)C2=O)=C1 WWLZNEZZFLXWAU-YTTGMZPUSA-N 0.000 description 1
- QIZPQMDZZCUOJP-HKBQPEDESA-N benzyl n-[4-[(3s)-1-[(4-fluorophenyl)methyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C1=CC(F)=CC=C1CN1C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N[C@@H](CCCCNC(=O)OCC=2C=CC=CC=2)C1=O QIZPQMDZZCUOJP-HKBQPEDESA-N 0.000 description 1
- DEZUUWXDTCVESL-YTTGMZPUSA-N benzyl n-[4-[(3s)-1-[(4-methoxyphenyl)methyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C1=CC(OC)=CC=C1CN1C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N[C@@H](CCCCNC(=O)OCC=2C=CC=CC=2)C1=O DEZUUWXDTCVESL-YTTGMZPUSA-N 0.000 description 1
- GLDBYRFWRBPXRG-YTTGMZPUSA-N benzyl n-[4-[(3s)-1-[(4-methylphenyl)methyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C1=CC(C)=CC=C1CN1C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N[C@@H](CCCCNC(=O)OCC=2C=CC=CC=2)C1=O GLDBYRFWRBPXRG-YTTGMZPUSA-N 0.000 description 1
- UJPBNLGVUXIGGT-PMERELPUSA-N benzyl n-[4-[(3s)-1-[(5-methylfuran-2-yl)methyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound O1C(C)=CC=C1CN1C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N[C@@H](CCCCNC(=O)OCC=2C=CC=CC=2)C1=O UJPBNLGVUXIGGT-PMERELPUSA-N 0.000 description 1
- WBLDCWZJVLCSBL-FLDQDSGZSA-N benzyl n-[4-[(3s)-1-[2-(1-methylpyrrolidin-2-yl)ethyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound CN1CCCC1CCN1C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N[C@@H](CCCCNC(=O)OCC=2C=CC=CC=2)C1=O WBLDCWZJVLCSBL-FLDQDSGZSA-N 0.000 description 1
- IGTZSPAKUFHRJZ-YTTGMZPUSA-N benzyl n-[4-[(3s)-1-[2-(cyclohexen-1-yl)ethyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N([C@H](C(N1CCC=2CCCCC=2)=O)CCCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 IGTZSPAKUFHRJZ-YTTGMZPUSA-N 0.000 description 1
- LQHRBUOKCYERDV-NDEPHWFRSA-N benzyl n-[4-[(3s)-1-[2-(dimethylamino)ethyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CCN(C)C)CCCNC(=O)OCC1=CC=CC=C1 LQHRBUOKCYERDV-NDEPHWFRSA-N 0.000 description 1
- OXNULWSVWITIGL-LJAQVGFWSA-N benzyl n-[4-[(3s)-1-[3-(dimethylamino)propyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CCCN(C)C)CCCNC(=O)OCC1=CC=CC=C1 OXNULWSVWITIGL-LJAQVGFWSA-N 0.000 description 1
- HDPCFWJULSQRDS-GJBCSVNNSA-N benzyl n-[4-[(3s)-1-[[(1s,4s,5s)-6,6-dimethyl-4-bicyclo[3.1.1]heptanyl]methyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)C[C@@H]1[C@@H]2C[C@H](CC1)C2(C)C)CCCNC(=O)OCC1=CC=CC=C1 HDPCFWJULSQRDS-GJBCSVNNSA-N 0.000 description 1
- BERMBUXMOKXCRD-HKBQPEDESA-N benzyl n-[4-[(3s)-1-benzyl-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N([C@H](C(N1CC=2C=CC=CC=2)=O)CCCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 BERMBUXMOKXCRD-HKBQPEDESA-N 0.000 description 1
- DWWFHQRTTZKMLK-NMXAJACMSA-N benzyl n-[4-[(3s)-1-butan-2-yl-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)C(C)CC)CCCNC(=O)OCC1=CC=CC=C1 DWWFHQRTTZKMLK-NMXAJACMSA-N 0.000 description 1
- LILRDAJXMFEENN-NDEPHWFRSA-N benzyl n-[4-[(3s)-1-butyl-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CCCC)CCCNC(=O)OCC1=CC=CC=C1 LILRDAJXMFEENN-NDEPHWFRSA-N 0.000 description 1
- PBIIQBJVAXTMLQ-NDEPHWFRSA-N benzyl n-[4-[(3s)-1-cyclobutyl-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N([C@H](C(N1C2CCC2)=O)CCCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 PBIIQBJVAXTMLQ-NDEPHWFRSA-N 0.000 description 1
- WFASHUQZKBUYTD-HKBQPEDESA-N benzyl n-[4-[(3s)-1-cycloheptyl-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N([C@H](C(N1C2CCCCCC2)=O)CCCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 WFASHUQZKBUYTD-HKBQPEDESA-N 0.000 description 1
- QNMCOGKHYWRGLZ-PMERELPUSA-N benzyl n-[4-[(3s)-1-cyclohexyl-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N([C@H](C(N1C2CCCCC2)=O)CCCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 QNMCOGKHYWRGLZ-PMERELPUSA-N 0.000 description 1
- IFDBPLNNFNHRIE-LJAQVGFWSA-N benzyl n-[4-[(3s)-1-cyclopentyl-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N([C@H](C(N1C2CCCC2)=O)CCCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 IFDBPLNNFNHRIE-LJAQVGFWSA-N 0.000 description 1
- QXWYPKQCECYSGV-MHZLTWQESA-N benzyl n-[4-[(3s)-1-cyclopropyl-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N([C@H](C(N1C2CC2)=O)CCCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 QXWYPKQCECYSGV-MHZLTWQESA-N 0.000 description 1
- GRPCEKXZPGBWRG-SANMLTNESA-N benzyl n-[4-[(3s)-1-ethyl-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CC)CCCNC(=O)OCC1=CC=CC=C1 GRPCEKXZPGBWRG-SANMLTNESA-N 0.000 description 1
- HHUJJHCPCXQJEE-QFIPXVFZSA-N benzyl n-[4-[(3s)-2,5-dioxo-1,9-dipropyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C1CN(CCC)CCC21C(=O)N[C@@H](CCCCNC(=O)OCC=1C=CC=CC=1)C(=O)N2CCC HHUJJHCPCXQJEE-QFIPXVFZSA-N 0.000 description 1
- PPCMAQWOYDCOQL-YYMSGCCCSA-N benzyl n-[4-[(3s)-2,5-dioxo-1-(1-phenylethyl)-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)C(C)C=1C=CC=CC=1)CCCNC(=O)OCC1=CC=CC=C1 PPCMAQWOYDCOQL-YYMSGCCCSA-N 0.000 description 1
- WSQLYVXSSXMMMF-WQMUIRCLSA-N benzyl n-[4-[(3s)-2,5-dioxo-1-(4-phenylbutan-2-yl)-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N([C@@H](CCCCNC(=O)OCC=1C=CC=CC=1)C1=O)C(=O)C2(CCN(CCC=3C=CC=CC=3)CC2)N1C(C)CCC1=CC=CC=C1 WSQLYVXSSXMMMF-WQMUIRCLSA-N 0.000 description 1
- KJMZTEXWBBCCSA-UMSFTDKQSA-N benzyl n-[4-[(3s)-2,5-dioxo-1-(4-phenylbutyl)-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N([C@H](C(N1CCCCC=2C=CC=CC=2)=O)CCCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 KJMZTEXWBBCCSA-UMSFTDKQSA-N 0.000 description 1
- HWXZDGVZJUMEQK-BTMGADRYSA-N benzyl n-[4-[(3s)-2,5-dioxo-1-pentan-2-yl-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)C(C)CCC)CCCNC(=O)OCC1=CC=CC=C1 HWXZDGVZJUMEQK-BTMGADRYSA-N 0.000 description 1
- HXXZCKSMLVXJQK-LJAQVGFWSA-N benzyl n-[4-[(3s)-2,5-dioxo-1-pentyl-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CCCCC)CCCNC(=O)OCC1=CC=CC=C1 HXXZCKSMLVXJQK-LJAQVGFWSA-N 0.000 description 1
- HBHNHSUPNRMJFZ-QFIPXVFZSA-N benzyl n-[4-[(3s)-2,5-dioxo-1-propyl-9-(1,3-thiazol-2-ylmethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3SC=CN=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 HBHNHSUPNRMJFZ-QFIPXVFZSA-N 0.000 description 1
- CVZISQRURPNUDS-SANMLTNESA-N benzyl n-[4-[(3s)-2,5-dioxo-1-propyl-9-(2,6,6-trimethylcyclohexene-1-carbonyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2C(CCCC=2C)(C)C)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 CVZISQRURPNUDS-SANMLTNESA-N 0.000 description 1
- LPTIZBMPJCCKDB-DEOSSOPVSA-N benzyl n-[4-[(3s)-2,5-dioxo-1-propyl-9-(2-thiophen-2-ylacetyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)CC=2SC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 LPTIZBMPJCCKDB-DEOSSOPVSA-N 0.000 description 1
- NWMGMTJRUJGYBM-VWLOTQADSA-N benzyl n-[4-[(3s)-2,5-dioxo-1-propyl-9-(2-thiophen-2-ylethylcarbamoyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NCCC=2SC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 NWMGMTJRUJGYBM-VWLOTQADSA-N 0.000 description 1
- VPCQKLLPUKYBNO-GPNIZQGCSA-N benzyl n-[4-[(3s)-2,5-dioxo-1-propyl-9-(3,5,5-trimethylhexyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC(C)CC(C)(C)C)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 VPCQKLLPUKYBNO-GPNIZQGCSA-N 0.000 description 1
- UJOXLSMCAFCWMA-QFIPXVFZSA-N benzyl n-[4-[(3s)-2,5-dioxo-1-propyl-9-(propylcarbamoyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C1CN(C(=O)NCCC)CCC21C(=O)N[C@@H](CCCCNC(=O)OCC=1C=CC=CC=1)C(=O)N2CCC UJOXLSMCAFCWMA-QFIPXVFZSA-N 0.000 description 1
- JUPSKNXTASFZEC-DEOSSOPVSA-N benzyl n-[4-[(3s)-2,5-dioxo-1-propyl-9-(pyridine-2-carbonyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2N=CC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 JUPSKNXTASFZEC-DEOSSOPVSA-N 0.000 description 1
- SOGZAJPBTRIXLT-DEOSSOPVSA-N benzyl n-[4-[(3s)-2,5-dioxo-1-propyl-9-(pyridine-3-carbonyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2C=NC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 SOGZAJPBTRIXLT-DEOSSOPVSA-N 0.000 description 1
- QRTYFLITBZZLQC-DEOSSOPVSA-N benzyl n-[4-[(3s)-2,5-dioxo-1-propyl-9-(pyridine-4-carbonyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2C=CN=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 QRTYFLITBZZLQC-DEOSSOPVSA-N 0.000 description 1
- LTMGLPXCOVGCHC-QHCPKHFHSA-N benzyl n-[4-[(3s)-2,5-dioxo-1-propyl-9-(pyrrolidine-1-carbonyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)N2CCCC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 LTMGLPXCOVGCHC-QHCPKHFHSA-N 0.000 description 1
- LGNXIIAHYPHQRW-DEOSSOPVSA-N benzyl n-[4-[(3s)-2,5-dioxo-1-propyl-9-(thiophen-2-ylmethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3SC=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 LGNXIIAHYPHQRW-DEOSSOPVSA-N 0.000 description 1
- SHAYQBQOANTXQE-QFIPXVFZSA-N benzyl n-[4-[(3s)-2,5-dioxo-1-propyl-9-(thiophene-2-carbonyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2SC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 SHAYQBQOANTXQE-QFIPXVFZSA-N 0.000 description 1
- ZILOZBFDPXSYKT-MHZLTWQESA-N benzyl n-[4-[(3s)-2,5-dioxo-1-propyl-9-[(2,4,5-trimethylphenyl)carbamoyl]-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C(=CC(C)=C(C)C=2)C)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 ZILOZBFDPXSYKT-MHZLTWQESA-N 0.000 description 1
- SYDMMXNJBDYLPR-DEOSSOPVSA-N benzyl n-[4-[(3s)-2,5-dioxo-1-propyl-9-[(2,4,6-tribromophenyl)carbamoyl]-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C(=CC(Br)=CC=2Br)Br)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 SYDMMXNJBDYLPR-DEOSSOPVSA-N 0.000 description 1
- APSXOQYAYIQYFU-DEOSSOPVSA-N benzyl n-[4-[(3s)-2,5-dioxo-1-propyl-9-[(2,4,6-trichlorophenyl)carbamoyl]-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C(=CC(Cl)=CC=2Cl)Cl)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 APSXOQYAYIQYFU-DEOSSOPVSA-N 0.000 description 1
- GQGXDNFJNNSRFL-MHZLTWQESA-N benzyl n-[4-[(3s)-2,5-dioxo-1-propyl-9-[(2,4,6-trimethoxyphenyl)methyl]-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C(=CC(OC)=CC=3OC)OC)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 GQGXDNFJNNSRFL-MHZLTWQESA-N 0.000 description 1
- JYJUMZNXPUFUBH-MHZLTWQESA-N benzyl n-[4-[(3s)-2,5-dioxo-1-propyl-9-[(2,4,6-trimethylphenyl)carbamoyl]-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C(=CC(C)=CC=2C)C)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 JYJUMZNXPUFUBH-MHZLTWQESA-N 0.000 description 1
- LSSBTHGMTIDVOP-XQUALCHDSA-N benzyl n-[4-[(3s)-2,5-dioxo-1-propyl-9-[(2s,3s,4r)-2,3,4,5-tetrahydroxypentyl]-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(C[C@H](O)[C@H](O)[C@H](O)CO)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 LSSBTHGMTIDVOP-XQUALCHDSA-N 0.000 description 1
- VVMWBMWVTZPMNC-ZOQUMNKXSA-N benzyl n-[4-[(3s)-2,5-dioxo-1-propyl-9-[(3,5,6-trimethylcyclohex-3-en-1-yl)methyl]-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC3C(C(C)C=C(C)C3)C)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 VVMWBMWVTZPMNC-ZOQUMNKXSA-N 0.000 description 1
- USTMJRVCXBRQAI-KMDXXIMOSA-N benzyl n-[4-[(3s)-2,5-dioxo-1-propyl-9-[(3s,4r)-3,4,5-trihydroxypentyl]-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC[C@H](O)[C@H](O)CO)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 USTMJRVCXBRQAI-KMDXXIMOSA-N 0.000 description 1
- ISDCCKWMADCOPG-PMERELPUSA-N benzyl n-[4-[(3s)-2,5-dioxo-1-propyl-9-[(4-pyrrolidin-1-ylphenyl)methyl]-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=CC(=CC=3)N3CCCC3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 ISDCCKWMADCOPG-PMERELPUSA-N 0.000 description 1
- FFUFUUPMRDQOGA-VWLOTQADSA-N benzyl n-[4-[(3s)-2,5-dioxo-1-propyl-9-[4-(trifluoromethyl)phenyl]sulfonyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)S(=O)(=O)C=2C=CC(=CC=2)C(F)(F)F)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 FFUFUUPMRDQOGA-VWLOTQADSA-N 0.000 description 1
- CEPQZBVBFYKANX-VWLOTQADSA-N benzyl n-[4-[(3s)-2,5-dioxo-1-propyl-9-[[4-(trifluoromethyl)phenyl]carbamoyl]-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C=CC(=CC=2)C(F)(F)F)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 CEPQZBVBFYKANX-VWLOTQADSA-N 0.000 description 1
- IXYUBNGFZPMCDN-MHZLTWQESA-N benzyl n-[4-[(3s)-2,5-dioxo-1-propyl-9-quinolin-2-yl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C=2N=C3C=CC=CC3=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 IXYUBNGFZPMCDN-MHZLTWQESA-N 0.000 description 1
- XAALCPOKNJXNIS-QFIPXVFZSA-N benzyl n-[4-[(3s)-2,5-dioxo-1-propyl-9-thiophen-2-ylsulfonyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)S(=O)(=O)C=2SC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 XAALCPOKNJXNIS-QFIPXVFZSA-N 0.000 description 1
- KRULLYLQQCPROO-PMERELPUSA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(1-phenyl-5-propylpyrazole-4-carbonyl)-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C2=C(N(N=C2)C=2C=CC=CC=2)CCC)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 KRULLYLQQCPROO-PMERELPUSA-N 0.000 description 1
- AMZBVOVFUBNCPM-SANMLTNESA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(2-phenoxyacetyl)-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)COC=2C=CC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 AMZBVOVFUBNCPM-SANMLTNESA-N 0.000 description 1
- CHFFKTLAONWHPQ-LJAQVGFWSA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(2-phenoxypyridine-3-carbonyl)-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2C(=NC=CC=2)OC=2C=CC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 CHFFKTLAONWHPQ-LJAQVGFWSA-N 0.000 description 1
- JIUNODKQQHYFQZ-SANMLTNESA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(2-phenylacetyl)-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)CC=2C=CC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 JIUNODKQQHYFQZ-SANMLTNESA-N 0.000 description 1
- KHQBYDMREWTMQI-SANMLTNESA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(2-phenylethanethioyl)-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=S)CC=2C=CC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 KHQBYDMREWTMQI-SANMLTNESA-N 0.000 description 1
- OKVDTZPFPNTRQI-CJEZNJPTSA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-(2-phenylpropyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CC(C)C=1C=CC=CC=1)CCCNC(=O)OCC1=CC=CC=C1 OKVDTZPFPNTRQI-CJEZNJPTSA-N 0.000 description 1
- USBRIZYOQQAJFM-HKBQPEDESA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-(2-piperidin-1-ylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N([C@H](C(N1CCN2CCCCC2)=O)CCCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 USBRIZYOQQAJFM-HKBQPEDESA-N 0.000 description 1
- MYDBDNCAYVYPIL-HKBQPEDESA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-(2-pyridin-2-ylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N([C@H](C(N1CCC=2N=CC=CC=2)=O)CCCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 MYDBDNCAYVYPIL-HKBQPEDESA-N 0.000 description 1
- APMCJKFQBQWYKW-HKBQPEDESA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-(2-pyridin-3-ylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N([C@H](C(N1CCC=2C=NC=CC=2)=O)CCCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 APMCJKFQBQWYKW-HKBQPEDESA-N 0.000 description 1
- VMCQIGCLNUYPCX-HKBQPEDESA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-(2-pyridin-4-ylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N([C@H](C(N1CCC=2C=CN=CC=2)=O)CCCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 VMCQIGCLNUYPCX-HKBQPEDESA-N 0.000 description 1
- WAFWWHPGLJHCTF-PMERELPUSA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-(2-thiophen-2-ylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N([C@H](C(N1CCC=2SC=CC=2)=O)CCCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 WAFWWHPGLJHCTF-PMERELPUSA-N 0.000 description 1
- JOHVBUOUJMRAME-XIFFEERXSA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-(3-phenylpropyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N([C@H](C(N1CCCC=2C=CC=CC=2)=O)CCCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 JOHVBUOUJMRAME-XIFFEERXSA-N 0.000 description 1
- MTNOEBASAUVFRL-PMERELPUSA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-(pyridin-3-ylmethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N([C@H](C(N1CC=2C=NC=CC=2)=O)CCCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 MTNOEBASAUVFRL-PMERELPUSA-N 0.000 description 1
- XVEBPBQQYYYJRJ-PMERELPUSA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-(pyridin-4-ylmethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N([C@H](C(N1CC=2C=CN=CC=2)=O)CCCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 XVEBPBQQYYYJRJ-PMERELPUSA-N 0.000 description 1
- WINUMHWAEGOLMG-LJAQVGFWSA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-(thiophen-2-ylmethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N([C@H](C(N1CC=2SC=CC=2)=O)CCCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 WINUMHWAEGOLMG-LJAQVGFWSA-N 0.000 description 1
- HTGSPUCPXLOOKZ-MHZLTWQESA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-prop-2-enyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)CC=C)CCCNC(=O)OCC1=CC=CC=C1 HTGSPUCPXLOOKZ-MHZLTWQESA-N 0.000 description 1
- PSQNUGICEULIKI-MHZLTWQESA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-prop-2-ynyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N([C@H](C(N1CC#C)=O)CCCCNC(=O)OCC=2C=CC=CC=2)C(=O)C1(CC1)CCN1CCC1=CC=CC=C1 PSQNUGICEULIKI-MHZLTWQESA-N 0.000 description 1
- FVWIMNBPAGIEMU-MHZLTWQESA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-propan-2-yl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC=3C=CC=CC=3)CC2)C(=O)N1)C(C)C)CCCNC(=O)OCC1=CC=CC=C1 FVWIMNBPAGIEMU-MHZLTWQESA-N 0.000 description 1
- WWAWWAIOHDXBPH-MHZLTWQESA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(2-phenylmethoxyacetyl)-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)COCC=2C=CC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 WWAWWAIOHDXBPH-MHZLTWQESA-N 0.000 description 1
- MZKDBBLSQPYSIB-NDEPHWFRSA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(2-phenylmethoxyethyl)-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCOCC=3C=CC=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 MZKDBBLSQPYSIB-NDEPHWFRSA-N 0.000 description 1
- QBHZMNHMSIEPGG-PMERELPUSA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(2-phenylphenyl)sulfonyl-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)S(=O)(=O)C=2C(=CC=CC=2)C=2C=CC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 QBHZMNHMSIEPGG-PMERELPUSA-N 0.000 description 1
- VDWRUHCEFPTBAE-LJAQVGFWSA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(2-phenylsulfanylpyridine-3-carbonyl)-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2C(=NC=CC=2)SC=2C=CC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 VDWRUHCEFPTBAE-LJAQVGFWSA-N 0.000 description 1
- XDWYSKOVUBMECC-NDEPHWFRSA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(3-phenylpropyl)-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCCC=3C=CC=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 XDWYSKOVUBMECC-NDEPHWFRSA-N 0.000 description 1
- MFFGKLNPQIADNH-HKBQPEDESA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(4-phenylbenzoyl)-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 MFFGKLNPQIADNH-HKBQPEDESA-N 0.000 description 1
- DFCLXEVITOXXCE-HKBQPEDESA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(4-phenylphenyl)sulfonyl-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 DFCLXEVITOXXCE-HKBQPEDESA-N 0.000 description 1
- QVOORWZNVSALRI-HKBQPEDESA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(6-phenylhexyl)-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCCCCCC=3C=CC=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 QVOORWZNVSALRI-HKBQPEDESA-N 0.000 description 1
- QZWUVTAMTKDFGS-VWLOTQADSA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(phenylcarbamoyl)-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C=CC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 QZWUVTAMTKDFGS-VWLOTQADSA-N 0.000 description 1
- NFCFYKPONBSTMV-QFIPXVFZSA-N benzyl n-[4-[(3s)-2,5-dioxo-9-(propan-2-ylcarbamoyl)-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC(C)C)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 NFCFYKPONBSTMV-QFIPXVFZSA-N 0.000 description 1
- YKOMWMLHDNVEJL-YTTGMZPUSA-N benzyl n-[4-[(3s)-2,5-dioxo-9-[(2-phenylmethoxyphenyl)methyl]-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C(=CC=CC=3)OCC=3C=CC=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 YKOMWMLHDNVEJL-YTTGMZPUSA-N 0.000 description 1
- LTOMIEUVHUBMHK-HKBQPEDESA-N benzyl n-[4-[(3s)-2,5-dioxo-9-[(2-phenylphenyl)carbamoyl]-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C(=CC=CC=2)C=2C=CC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 LTOMIEUVHUBMHK-HKBQPEDESA-N 0.000 description 1
- HCLJYSGFGZREFM-YTTGMZPUSA-N benzyl n-[4-[(3s)-2,5-dioxo-9-[(3-phenoxyphenyl)methyl]-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=C(OC=4C=CC=CC=4)C=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 HCLJYSGFGZREFM-YTTGMZPUSA-N 0.000 description 1
- RRODOVJRELRZAA-XIFFEERXSA-N benzyl n-[4-[(3s)-2,5-dioxo-9-[(3-phenylmethoxyphenyl)methyl]-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=C(OCC=4C=CC=CC=4)C=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 RRODOVJRELRZAA-XIFFEERXSA-N 0.000 description 1
- ORZPUWSBLDZTEA-HKBQPEDESA-N benzyl n-[4-[(3s)-2,5-dioxo-9-[(4-phenoxyphenyl)carbamoyl]-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C=CC(OC=3C=CC=CC=3)=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 ORZPUWSBLDZTEA-HKBQPEDESA-N 0.000 description 1
- ONWPHQOZKMBFRI-YTTGMZPUSA-N benzyl n-[4-[(3s)-2,5-dioxo-9-[(4-phenoxyphenyl)methyl]-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=CC(OC=4C=CC=CC=4)=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 ONWPHQOZKMBFRI-YTTGMZPUSA-N 0.000 description 1
- IHIJSWLMAINPPR-XIFFEERXSA-N benzyl n-[4-[(3s)-2,5-dioxo-9-[(4-phenylmethoxyphenyl)methyl]-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=CC(OCC=4C=CC=CC=4)=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 IHIJSWLMAINPPR-XIFFEERXSA-N 0.000 description 1
- TZBAGYQSFSUWDJ-HKBQPEDESA-N benzyl n-[4-[(3s)-2,5-dioxo-9-[(4-phenylphenyl)carbamoyl]-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 TZBAGYQSFSUWDJ-HKBQPEDESA-N 0.000 description 1
- ROQBDENVQXYUSA-NDEPHWFRSA-N benzyl n-[4-[(3s)-2,5-dioxo-9-[(4-propan-2-ylphenyl)carbamoyl]-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C=CC(=CC=2)C(C)C)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 ROQBDENVQXYUSA-NDEPHWFRSA-N 0.000 description 1
- AZAZXPCWAGORMN-NDEPHWFRSA-N benzyl n-[4-[(3s)-2,5-dioxo-9-[(5-phenyl-1h-pyrazol-4-yl)methyl]-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC3=C(NN=C3)C=3C=CC=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 AZAZXPCWAGORMN-NDEPHWFRSA-N 0.000 description 1
- XAVIHTCOJBOVNH-SANMLTNESA-N benzyl n-[4-[(3s)-2,5-dioxo-9-[(6-oxo-[1,3]dioxolo[4,5-g]chromen-8-yl)methylcarbamoyl]-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NCC=2C=3C=C4OCOC4=CC=3OC(=O)C=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 XAVIHTCOJBOVNH-SANMLTNESA-N 0.000 description 1
- VSRDURNGQYDDJX-DEOSSOPVSA-N benzyl n-[4-[(3s)-2,5-dioxo-9-pentylsulfonyl-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C1CN(S(=O)(=O)CCCCC)CCC21C(=O)N[C@@H](CCCCNC(=O)OCC=1C=CC=CC=1)C(=O)N2CCC VSRDURNGQYDDJX-DEOSSOPVSA-N 0.000 description 1
- GDCUZPXFOUGWSW-QFIPXVFZSA-N benzyl n-[4-[(3s)-2,5-dioxo-9-propan-2-ylsulfonyl-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)S(=O)(=O)C(C)C)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 GDCUZPXFOUGWSW-QFIPXVFZSA-N 0.000 description 1
- YIWXURIMXOJVHO-NRFANRHFSA-N benzyl n-[4-[(3s)-2,5-dioxo-9-propanoyl-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)CC)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 YIWXURIMXOJVHO-NRFANRHFSA-N 0.000 description 1
- WSERSCZPBIFZBH-NRFANRHFSA-N benzyl n-[4-[(3s)-9-(1,2-oxazole-5-carbonyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2ON=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 WSERSCZPBIFZBH-NRFANRHFSA-N 0.000 description 1
- LIMZBMQKAZXNCV-MHZLTWQESA-N benzyl n-[4-[(3s)-9-(1-benzofuran-2-ylmethyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3OC4=CC=CC=C4C=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 LIMZBMQKAZXNCV-MHZLTWQESA-N 0.000 description 1
- BOYQOKJKXNGNBT-QFIPXVFZSA-N benzyl n-[4-[(3s)-9-(2,2-dimethylpropanoyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C(C)(C)C)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 BOYQOKJKXNGNBT-QFIPXVFZSA-N 0.000 description 1
- DDVMRYHVRKSYSH-QHCPKHFHSA-N benzyl n-[4-[(3s)-9-(2,2-dimethylpropyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC(C)(C)C)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 DDVMRYHVRKSYSH-QHCPKHFHSA-N 0.000 description 1
- JJEIQYWFBCRDHT-SANMLTNESA-N benzyl n-[4-[(3s)-9-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=C4OCCOC4=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 JJEIQYWFBCRDHT-SANMLTNESA-N 0.000 description 1
- WGEYACOSYNPAPX-VWLOTQADSA-N benzyl n-[4-[(3s)-9-(2,5-dimethoxyphenyl)sulfonyl-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)S(=O)(=O)C=2C(=CC=C(OC)C=2)OC)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 WGEYACOSYNPAPX-VWLOTQADSA-N 0.000 description 1
- ASALBAACQGDTSV-RXBHZZDJSA-N benzyl n-[4-[(3s)-9-(2,6-dimethylhept-5-enyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC(C)CCC=C(C)C)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 ASALBAACQGDTSV-RXBHZZDJSA-N 0.000 description 1
- CBESJMYHAODPAL-VWLOTQADSA-N benzyl n-[4-[(3s)-9-(2-cyclopentylacetyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)CC2CCCC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 CBESJMYHAODPAL-VWLOTQADSA-N 0.000 description 1
- ZZAXEEGVXXXSSP-GPNIZQGCSA-N benzyl n-[4-[(3s)-9-(2-ethylhexyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C1CN(CC(CC)CCCC)CCC21C(=O)N[C@@H](CCCCNC(=O)OCC=1C=CC=CC=1)C(=O)N2CCC ZZAXEEGVXXXSSP-GPNIZQGCSA-N 0.000 description 1
- DYKRJIDNTWHBPC-VWLOTQADSA-N benzyl n-[4-[(3s)-9-(2-fluorobenzoyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2C(=CC=CC=2)F)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 DYKRJIDNTWHBPC-VWLOTQADSA-N 0.000 description 1
- MMEHFIJXXWXADM-NRFANRHFSA-N benzyl n-[4-[(3s)-9-(2-hydroxyethyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCO)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 MMEHFIJXXWXADM-NRFANRHFSA-N 0.000 description 1
- IXMZPKXKFDMTDC-NRFANRHFSA-N benzyl n-[4-[(3s)-9-(2-methoxyacetyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)COC)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 IXMZPKXKFDMTDC-NRFANRHFSA-N 0.000 description 1
- WEQZMIFMXGLDTF-VWLOTQADSA-N benzyl n-[4-[(3s)-9-(2-methoxybenzoyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2C(=CC=CC=2)OC)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 WEQZMIFMXGLDTF-VWLOTQADSA-N 0.000 description 1
- VSVYIZKQYZODKL-NDEPHWFRSA-N benzyl n-[4-[(3s)-9-(2-methoxydibenzofuran-3-yl)sulfonyl-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)S(=O)(=O)C=2C(=CC=3C4=CC=CC=C4OC=3C=2)OC)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 VSVYIZKQYZODKL-NDEPHWFRSA-N 0.000 description 1
- JUWUQJKAIMXLDL-SANMLTNESA-N benzyl n-[4-[(3s)-9-(2-methylbenzoyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2C(=CC=CC=2)C)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 JUWUQJKAIMXLDL-SANMLTNESA-N 0.000 description 1
- OHVYAMNIQWXRDR-QFIPXVFZSA-N benzyl n-[4-[(3s)-9-(2-methylpropanoyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C(C)C)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 OHVYAMNIQWXRDR-QFIPXVFZSA-N 0.000 description 1
- KJIIETOSKYYENU-QHCPKHFHSA-N benzyl n-[4-[(3s)-9-(2-methylpropyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC(C)C)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 KJIIETOSKYYENU-QHCPKHFHSA-N 0.000 description 1
- ZTFDDJOPRBUORE-VWLOTQADSA-N benzyl n-[4-[(3s)-9-(2-tert-butyl-5-methylpyrazole-3-carbonyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2N(N=C(C)C=2)C(C)(C)C)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 ZTFDDJOPRBUORE-VWLOTQADSA-N 0.000 description 1
- TXAKUUREYIUEDU-VWLOTQADSA-N benzyl n-[4-[(3s)-9-(3,4-dichlorophenyl)sulfonyl-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)S(=O)(=O)C=2C=C(Cl)C(Cl)=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 TXAKUUREYIUEDU-VWLOTQADSA-N 0.000 description 1
- PSPZMCXWINHIJJ-ACEFPKFPSA-N benzyl n-[4-[(3s)-9-(3,7-dimethyloct-6-enyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC(C)CCC=C(C)C)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 PSPZMCXWINHIJJ-ACEFPKFPSA-N 0.000 description 1
- IBRRHOLOMRAXGH-SANMLTNESA-N benzyl n-[4-[(3s)-9-(3-cyanobenzoyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2C=C(C=CC=2)C#N)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 IBRRHOLOMRAXGH-SANMLTNESA-N 0.000 description 1
- IUFYDSGPMADCTH-SANMLTNESA-N benzyl n-[4-[(3s)-9-(3-cyclopentylpropanoyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)CCC2CCCC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 IUFYDSGPMADCTH-SANMLTNESA-N 0.000 description 1
- PSJFTURQYIPGOR-VWLOTQADSA-N benzyl n-[4-[(3s)-9-(3-fluorobenzoyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2C=C(F)C=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 PSJFTURQYIPGOR-VWLOTQADSA-N 0.000 description 1
- CNOBOCLPXCKYDL-SANMLTNESA-N benzyl n-[4-[(3s)-9-(3-methoxybenzoyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2C=C(OC)C=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 CNOBOCLPXCKYDL-SANMLTNESA-N 0.000 description 1
- VGGUUHIARGJAMQ-SANMLTNESA-N benzyl n-[4-[(3s)-9-(3-methylbenzoyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2C=C(C)C=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 VGGUUHIARGJAMQ-SANMLTNESA-N 0.000 description 1
- SNWALOWKTLNMQG-QHCPKHFHSA-N benzyl n-[4-[(3s)-9-(3-methylbutanoyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)CC(C)C)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 SNWALOWKTLNMQG-QHCPKHFHSA-N 0.000 description 1
- XZQMRSNSFYSCSP-DEOSSOPVSA-N benzyl n-[4-[(3s)-9-(3-methylbutyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCC(C)C)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 XZQMRSNSFYSCSP-DEOSSOPVSA-N 0.000 description 1
- UQDJUMYSEBETQR-QHCPKHFHSA-N benzyl n-[4-[(3s)-9-(3-methylsulfanylpropyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCCSC)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 UQDJUMYSEBETQR-QHCPKHFHSA-N 0.000 description 1
- CFHPJKFTYUYMMG-IBGZPJMESA-N benzyl n-[4-[(3s)-9-(4-bromo-2,5-dichlorothiophen-3-yl)sulfonyl-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)S(=O)(=O)C=2C(=C(Cl)SC=2Cl)Br)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 CFHPJKFTYUYMMG-IBGZPJMESA-N 0.000 description 1
- OQKPLBIEQTTXJY-VWLOTQADSA-N benzyl n-[4-[(3s)-9-(4-chlorophenyl)sulfonyl-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)S(=O)(=O)C=2C=CC(Cl)=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 OQKPLBIEQTTXJY-VWLOTQADSA-N 0.000 description 1
- HYMQQCAMOWYHJZ-VWLOTQADSA-N benzyl n-[4-[(3s)-9-(4-fluorobenzoyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2C=CC(F)=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 HYMQQCAMOWYHJZ-VWLOTQADSA-N 0.000 description 1
- VSEVRUFEIDJDLC-SANMLTNESA-N benzyl n-[4-[(3s)-9-(4-methoxybenzoyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2C=CC(OC)=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 VSEVRUFEIDJDLC-SANMLTNESA-N 0.000 description 1
- DCDATAYZUHHPCR-SANMLTNESA-N benzyl n-[4-[(3s)-9-(4-methoxyphenyl)sulfonyl-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)S(=O)(=O)C=2C=CC(OC)=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 DCDATAYZUHHPCR-SANMLTNESA-N 0.000 description 1
- WMDIERGDPPTILP-SANMLTNESA-N benzyl n-[4-[(3s)-9-(4-methylbenzoyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2C=CC(C)=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 WMDIERGDPPTILP-SANMLTNESA-N 0.000 description 1
- XHPNKMJZLLABSK-SANMLTNESA-N benzyl n-[4-[(3s)-9-(4-methylsulfonylphenyl)sulfonyl-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)S(=O)(=O)C=2C=CC(=CC=2)S(C)(=O)=O)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 XHPNKMJZLLABSK-SANMLTNESA-N 0.000 description 1
- OBYUDBRRMRADGI-NRFANRHFSA-N benzyl n-[4-[(3s)-9-(4-methylthiadiazole-5-carbonyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C2=C(N=NS2)C)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 OBYUDBRRMRADGI-NRFANRHFSA-N 0.000 description 1
- CJIXLXDWTOMZFI-VWLOTQADSA-N benzyl n-[4-[(3s)-9-(4-nitrophenyl)sulfonyl-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)S(=O)(=O)C=2C=CC(=CC=2)[N+]([O-])=O)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 CJIXLXDWTOMZFI-VWLOTQADSA-N 0.000 description 1
- QBQVNQINSLEUHO-DEOSSOPVSA-N benzyl n-[4-[(3s)-9-(5-hydroxypentyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CCCCCO)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 QBQVNQINSLEUHO-DEOSSOPVSA-N 0.000 description 1
- UBRHBHJDFDNEQY-MHZLTWQESA-N benzyl n-[4-[(3s)-9-(5-methyl-2-phenyltriazole-4-carbonyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2C(=NN(N=2)C=2C=CC=CC=2)C)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 UBRHBHJDFDNEQY-MHZLTWQESA-N 0.000 description 1
- JEFRWNZVHWTKGG-MHZLTWQESA-N benzyl n-[4-[(3s)-9-(5-methyl-3-phenyl-1,2-oxazole-4-carbonyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2C(=NOC=2C)C=2C=CC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 JEFRWNZVHWTKGG-MHZLTWQESA-N 0.000 description 1
- MVRGODJARUHNMD-SANMLTNESA-N benzyl n-[4-[(3s)-9-(5-tert-butyl-2-methylfuran-3-carbonyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C2=C(OC(=C2)C(C)(C)C)C)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 MVRGODJARUHNMD-SANMLTNESA-N 0.000 description 1
- LCQSNZNUZTVJFR-VWLOTQADSA-N benzyl n-[4-[(3s)-9-(benzoylcarbamoyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC(=O)C=2C=CC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 LCQSNZNUZTVJFR-VWLOTQADSA-N 0.000 description 1
- WJFUIXQTLCRDJM-SANMLTNESA-N benzyl n-[4-[(3s)-9-(benzylcarbamoyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NCC=2C=CC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 WJFUIXQTLCRDJM-SANMLTNESA-N 0.000 description 1
- UYTVZZZSKOKSNX-QHCPKHFHSA-N benzyl n-[4-[(3s)-9-(butylcarbamoyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C1CN(C(=O)NCCCC)CCC21C(=O)N[C@@H](CCCCNC(=O)OCC=1C=CC=CC=1)C(=O)N2CCC UYTVZZZSKOKSNX-QHCPKHFHSA-N 0.000 description 1
- QIOWFFFCRPJCFL-LJAQVGFWSA-N benzyl n-[4-[(3s)-9-(carbazole-9-carbonyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)N2C3=CC=CC=C3C3=CC=CC=C32)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 QIOWFFFCRPJCFL-LJAQVGFWSA-N 0.000 description 1
- MIUBLSKJKDMMAR-QHCPKHFHSA-N benzyl n-[4-[(3s)-9-(cyclobutanecarbonyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C2CCC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 MIUBLSKJKDMMAR-QHCPKHFHSA-N 0.000 description 1
- SECOPQHUNGTVHV-VWLOTQADSA-N benzyl n-[4-[(3s)-9-(cyclohexanecarbonyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C2CCCCC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 SECOPQHUNGTVHV-VWLOTQADSA-N 0.000 description 1
- UDGLHXYLDRYXCQ-VWLOTQADSA-N benzyl n-[4-[(3s)-9-(cyclohexylcarbamoyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC2CCCCC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 UDGLHXYLDRYXCQ-VWLOTQADSA-N 0.000 description 1
- DEOPPEZIEOQZSY-SANMLTNESA-N benzyl n-[4-[(3s)-9-(cyclohexylmethyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC3CCCCC3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 DEOPPEZIEOQZSY-SANMLTNESA-N 0.000 description 1
- PABLQMLBVNUXGF-DEOSSOPVSA-N benzyl n-[4-[(3s)-9-(cyclopentanecarbonyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C2CCCC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 PABLQMLBVNUXGF-DEOSSOPVSA-N 0.000 description 1
- IVQVDSZNRLGEJS-QFIPXVFZSA-N benzyl n-[4-[(3s)-9-(cyclopropanecarbonyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C2CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 IVQVDSZNRLGEJS-QFIPXVFZSA-N 0.000 description 1
- VXZWETKSRKPNBO-QHCPKHFHSA-N benzyl n-[4-[(3s)-9-(cyclopropylmethyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC3CC3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 VXZWETKSRKPNBO-QHCPKHFHSA-N 0.000 description 1
- AFJOBMXAZXDTSC-QHCPKHFHSA-N benzyl n-[4-[(3s)-9-(diethylcarbamoyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)N(CC)CC)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 AFJOBMXAZXDTSC-QHCPKHFHSA-N 0.000 description 1
- YDQUZVIYNSSWLL-NRFANRHFSA-N benzyl n-[4-[(3s)-9-(dimethylcarbamoyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)N(C)C)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 YDQUZVIYNSSWLL-NRFANRHFSA-N 0.000 description 1
- WNKXFZPBOUZCJZ-HKBQPEDESA-N benzyl n-[4-[(3s)-9-(diphenylcarbamoyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)N(C=2C=CC=CC=2)C=2C=CC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 WNKXFZPBOUZCJZ-HKBQPEDESA-N 0.000 description 1
- INAMQDPRTQVBLC-NRFANRHFSA-N benzyl n-[4-[(3s)-9-(ethylcarbamoyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NCC)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 INAMQDPRTQVBLC-NRFANRHFSA-N 0.000 description 1
- VQVQJPNRLFTKNH-QFIPXVFZSA-N benzyl n-[4-[(3s)-9-(furan-2-carbonyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2OC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 VQVQJPNRLFTKNH-QFIPXVFZSA-N 0.000 description 1
- AFQYFYOLRAXIOA-DEOSSOPVSA-N benzyl n-[4-[(3s)-9-(furan-2-ylmethyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3OC=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 AFQYFYOLRAXIOA-DEOSSOPVSA-N 0.000 description 1
- GTPGXNDVPXNZMA-QFIPXVFZSA-N benzyl n-[4-[(3s)-9-(furan-2-ylsulfonyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)S(=O)(=O)C=2OC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 GTPGXNDVPXNZMA-QFIPXVFZSA-N 0.000 description 1
- HGPQUZFHSWOBEH-VWLOTQADSA-N benzyl n-[4-[(3s)-9-(hexylcarbamoyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C1CN(C(=O)NCCCCCC)CCC21C(=O)N[C@@H](CCCCNC(=O)OCC=1C=CC=CC=1)C(=O)N2CCC HGPQUZFHSWOBEH-VWLOTQADSA-N 0.000 description 1
- OOSGZWRNDUCALV-QHCPKHFHSA-N benzyl n-[4-[(3s)-9-(morpholine-4-carbonyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)N2CCOCC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 OOSGZWRNDUCALV-QHCPKHFHSA-N 0.000 description 1
- SSAJAPZOCYDHGE-PMERELPUSA-N benzyl n-[4-[(3s)-9-(naphthalen-1-ylmethyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C4=CC=CC=C4C=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 SSAJAPZOCYDHGE-PMERELPUSA-N 0.000 description 1
- CBZVGAYRNRRZMB-MHZLTWQESA-N benzyl n-[4-[(3s)-9-(octylcarbamoyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C1CN(C(=O)NCCCCCCCC)CCC21C(=O)N[C@@H](CCCCNC(=O)OCC=1C=CC=CC=1)C(=O)N2CCC CBZVGAYRNRRZMB-MHZLTWQESA-N 0.000 description 1
- LMPIFXQXYNHKIW-PMERELPUSA-N benzyl n-[4-[(3s)-9-[(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)methyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C(N(C=4C=CC=CC=4)N(C)C=3C)=O)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 LMPIFXQXYNHKIW-PMERELPUSA-N 0.000 description 1
- NQUPJUIONDOOFR-DEOSSOPVSA-N benzyl n-[4-[(3s)-9-[(2,5-difluorophenyl)carbamoyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C(=CC=C(F)C=2)F)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 NQUPJUIONDOOFR-DEOSSOPVSA-N 0.000 description 1
- UTTRVUGPWNZTTM-SANMLTNESA-N benzyl n-[4-[(3s)-9-[(2,5-dimethylphenyl)carbamoyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C(=CC=C(C)C=2)C)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 UTTRVUGPWNZTTM-SANMLTNESA-N 0.000 description 1
- NJBCVVVGWNFWHA-SANMLTNESA-N benzyl n-[4-[(3s)-9-[(2,6-dibromo-4-ethylphenyl)carbamoyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C(=CC(CC)=CC=2Br)Br)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 NJBCVVVGWNFWHA-SANMLTNESA-N 0.000 description 1
- BTCVMUHNSDNFEV-SANMLTNESA-N benzyl n-[4-[(3s)-9-[(2,6-dimethylphenyl)carbamoyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C(=CC=CC=2C)C)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 BTCVMUHNSDNFEV-SANMLTNESA-N 0.000 description 1
- CEAVWLFFTDIBNP-QHCPKHFHSA-N benzyl n-[4-[(3s)-9-[(2-acetamido-4-methyl-1,3-thiazol-5-yl)sulfonyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)S(=O)(=O)C2=C(N=C(NC(C)=O)S2)C)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 CEAVWLFFTDIBNP-QHCPKHFHSA-N 0.000 description 1
- DFLXIZMNLUOMRQ-LJAQVGFWSA-N benzyl n-[4-[(3s)-9-[(2-ethyl-6-propan-2-ylphenyl)carbamoyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C(=CC=CC=2CC)C(C)C)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 DFLXIZMNLUOMRQ-LJAQVGFWSA-N 0.000 description 1
- HFEMJWJIQCADNA-VWLOTQADSA-N benzyl n-[4-[(3s)-9-[(2-hydroxyphenyl)methyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C(=CC=CC=3)O)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 HFEMJWJIQCADNA-VWLOTQADSA-N 0.000 description 1
- AOUQGYIBRUDJAZ-SANMLTNESA-N benzyl n-[4-[(3s)-9-[(2-methoxyphenyl)methyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C(=CC=CC=3)OC)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 AOUQGYIBRUDJAZ-SANMLTNESA-N 0.000 description 1
- RGERFXJDIMCBTC-VWLOTQADSA-N benzyl n-[4-[(3s)-9-[(2-methylsulfanylphenyl)carbamoyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C(=CC=CC=2)SC)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 RGERFXJDIMCBTC-VWLOTQADSA-N 0.000 description 1
- PGSKQOJNAXRYHH-KDDYYSGWSA-N benzyl n-[4-[(3s)-9-[(2s,3r,4r,5r)-2-acetamido-3,4,5,6-tetrahydroxyhexyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(C[C@H](NC(C)=O)[C@@H](O)[C@@H](O)[C@H](O)CO)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 PGSKQOJNAXRYHH-KDDYYSGWSA-N 0.000 description 1
- IMWACUZMKXQEKZ-VWLOTQADSA-N benzyl n-[4-[(3s)-9-[(3,4-dichlorophenyl)carbamoyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C=C(Cl)C(Cl)=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 IMWACUZMKXQEKZ-VWLOTQADSA-N 0.000 description 1
- XCQPPWCEFNOIAY-MHZLTWQESA-N benzyl n-[4-[(3s)-9-[(3,4-dimethylphenyl)carbamoyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C=C(C)C(C)=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 XCQPPWCEFNOIAY-MHZLTWQESA-N 0.000 description 1
- MVFGFTUDVLSSSG-HKBQPEDESA-N benzyl n-[4-[(3s)-9-[(3,5-dimethyl-1-phenylpyrazol-4-yl)methyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC3=C(N(N=C3C)C=3C=CC=CC=3)C)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 MVFGFTUDVLSSSG-HKBQPEDESA-N 0.000 description 1
- YICUVPUAGKWKOC-HKBQPEDESA-N benzyl n-[4-[(3s)-9-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 YICUVPUAGKWKOC-HKBQPEDESA-N 0.000 description 1
- UGUDQRARGWUVJW-VWLOTQADSA-N benzyl n-[4-[(3s)-9-[(3-chlorophenyl)carbamoyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C=C(Cl)C=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 UGUDQRARGWUVJW-VWLOTQADSA-N 0.000 description 1
- XVGONOXAYMYMOT-MHZLTWQESA-N benzyl n-[4-[(3s)-9-[(3-cyanophenyl)methyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=C(C=CC=3)C#N)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 XVGONOXAYMYMOT-MHZLTWQESA-N 0.000 description 1
- PNMCVZSYGGOFEW-SANMLTNESA-N benzyl n-[4-[(3s)-9-[(3-fluorophenyl)methyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=C(F)C=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 PNMCVZSYGGOFEW-SANMLTNESA-N 0.000 description 1
- FVDHGXBECMFNCH-SANMLTNESA-N benzyl n-[4-[(3s)-9-[(3-hydroxyphenyl)methyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=C(O)C=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 FVDHGXBECMFNCH-SANMLTNESA-N 0.000 description 1
- CZNSBFPSZSVHPK-YTTGMZPUSA-N benzyl n-[4-[(3s)-9-[(3-methoxy-4-phenylmethoxyphenyl)methyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=C(OC)C(OCC=4C=CC=CC=4)=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 CZNSBFPSZSVHPK-YTTGMZPUSA-N 0.000 description 1
- DBCPPGLZNCZWIN-MHZLTWQESA-N benzyl n-[4-[(3s)-9-[(3-methyl-1-benzothiophen-2-yl)methyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC3=C(C4=CC=CC=C4S3)C)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 DBCPPGLZNCZWIN-MHZLTWQESA-N 0.000 description 1
- LEVZZURTNKMMNU-SANMLTNESA-N benzyl n-[4-[(3s)-9-[(3-methylphenyl)carbamoyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C=C(C)C=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 LEVZZURTNKMMNU-SANMLTNESA-N 0.000 description 1
- OLTISNWCCRXVLC-NDEPHWFRSA-N benzyl n-[4-[(3s)-9-[(4-acetamidophenyl)methyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=CC(NC(C)=O)=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 OLTISNWCCRXVLC-NDEPHWFRSA-N 0.000 description 1
- KHDLILCUQJCZHL-VWLOTQADSA-N benzyl n-[4-[(3s)-9-[(4-bromophenyl)carbamoyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C=CC(Br)=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 KHDLILCUQJCZHL-VWLOTQADSA-N 0.000 description 1
- UKQCNEMBKXHPDU-LJAQVGFWSA-N benzyl n-[4-[(3s)-9-[(4-butoxyphenyl)carbamoyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C1=CC(OCCCC)=CC=C1NC(=O)N1CCC2(C(N[C@@H](CCCCNC(=O)OCC=3C=CC=CC=3)C(=O)N2CCC)=O)CC1 UKQCNEMBKXHPDU-LJAQVGFWSA-N 0.000 description 1
- NSYBHPDSMWAFGH-LJAQVGFWSA-N benzyl n-[4-[(3s)-9-[(4-butylphenyl)carbamoyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C1=CC(CCCC)=CC=C1NC(=O)N1CCC2(C(N[C@@H](CCCCNC(=O)OCC=3C=CC=CC=3)C(=O)N2CCC)=O)CC1 NSYBHPDSMWAFGH-LJAQVGFWSA-N 0.000 description 1
- DVSLIUNMIFDQJU-VWLOTQADSA-N benzyl n-[4-[(3s)-9-[(4-chlorophenyl)carbamoyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C=CC(Cl)=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 DVSLIUNMIFDQJU-VWLOTQADSA-N 0.000 description 1
- QCFZUGZCLVYKNK-SANMLTNESA-N benzyl n-[4-[(3s)-9-[(4-chlorophenyl)methyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=CC(Cl)=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 QCFZUGZCLVYKNK-SANMLTNESA-N 0.000 description 1
- MGLZDIHFMAZHLL-VWLOTQADSA-N benzyl n-[4-[(3s)-9-[(4-fluorophenyl)carbamoyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C=CC(F)=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 MGLZDIHFMAZHLL-VWLOTQADSA-N 0.000 description 1
- QVTAUIAXYYIWCK-SANMLTNESA-N benzyl n-[4-[(3s)-9-[(4-fluorophenyl)methyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=CC(F)=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 QVTAUIAXYYIWCK-SANMLTNESA-N 0.000 description 1
- XUCHVWFYYLQPKB-XIFFEERXSA-N benzyl n-[4-[(3s)-9-[(4-heptoxyphenyl)methyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C1=CC(OCCCCCCC)=CC=C1CN1CCC2(C(N[C@@H](CCCCNC(=O)OCC=3C=CC=CC=3)C(=O)N2CCC)=O)CC1 XUCHVWFYYLQPKB-XIFFEERXSA-N 0.000 description 1
- ACYLWKZMNOPUHJ-HKBQPEDESA-N benzyl n-[4-[(3s)-9-[(4-hexoxy-3-methoxyphenyl)methyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C1=C(OC)C(OCCCCCC)=CC=C1CN1CCC2(C(N[C@@H](CCCCNC(=O)OCC=3C=CC=CC=3)C(=O)N2CCC)=O)CC1 ACYLWKZMNOPUHJ-HKBQPEDESA-N 0.000 description 1
- BVKKKOZBAXDASW-MHZLTWQESA-N benzyl n-[4-[(3s)-9-[(4-methoxyphenyl)methyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=CC(OC)=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 BVKKKOZBAXDASW-MHZLTWQESA-N 0.000 description 1
- NMJRVEVCABJDFO-SANMLTNESA-N benzyl n-[4-[(3s)-9-[(4-methylphenyl)carbamoyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C=CC(C)=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 NMJRVEVCABJDFO-SANMLTNESA-N 0.000 description 1
- RZDPGDJGCZPFNA-SANMLTNESA-N benzyl n-[4-[(3s)-9-[(4-methylsulfanylphenyl)carbamoyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C=CC(SC)=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 RZDPGDJGCZPFNA-SANMLTNESA-N 0.000 description 1
- NPVSNQHVQBGYQF-UMSFTDKQSA-N benzyl n-[4-[(3s)-9-[(4-octoxyphenyl)methyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C1=CC(OCCCCCCCC)=CC=C1CN1CCC2(C(N[C@@H](CCCCNC(=O)OCC=3C=CC=CC=3)C(=O)N2CCC)=O)CC1 NPVSNQHVQBGYQF-UMSFTDKQSA-N 0.000 description 1
- BSQIBNUESKPCHJ-LJAQVGFWSA-N benzyl n-[4-[(3s)-9-[(4-tert-butylphenyl)methyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=CC(=CC=3)C(C)(C)C)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 BSQIBNUESKPCHJ-LJAQVGFWSA-N 0.000 description 1
- CWNKYJHKBZAXOU-ZAPYXSEASA-N benzyl n-[4-[(3s)-9-[(e)-2-methylbut-1-enyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)\C=C(/C)CC)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 CWNKYJHKBZAXOU-ZAPYXSEASA-N 0.000 description 1
- CAPKCAPYWQVFED-FKCGAAFESA-N benzyl n-[4-[(3s)-9-[(e)-3-[4-(dimethylamino)phenyl]prop-1-enyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)\C=C\CC=2C=CC(=CC=2)N(C)C)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 CAPKCAPYWQVFED-FKCGAAFESA-N 0.000 description 1
- FSWZMFISTFMFCL-IMBQCAHCSA-N benzyl n-[4-[(3s)-9-[(e)-dec-1-enyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C1CN(/C=C/CCCCCCCC)CCC21C(=O)N[C@@H](CCCCNC(=O)OCC=1C=CC=CC=1)C(=O)N2CCC FSWZMFISTFMFCL-IMBQCAHCSA-N 0.000 description 1
- LDVOZWYGLSVNIT-MHZLTWQESA-N benzyl n-[4-[(3s)-9-[2-(3-methoxyphenyl)acetyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)CC=2C=C(OC)C=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 LDVOZWYGLSVNIT-MHZLTWQESA-N 0.000 description 1
- AQGBTJJEPPSAQK-MHZLTWQESA-N benzyl n-[4-[(3s)-9-[2-(4-methoxyphenyl)acetyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)CC=2C=CC(OC)=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 AQGBTJJEPPSAQK-MHZLTWQESA-N 0.000 description 1
- JBTRPWAZKNCNCE-DEOSSOPVSA-N benzyl n-[4-[(3s)-9-[2-chloro-4-(trifluoromethyl)phenyl]sulfonyl-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)S(=O)(=O)C=2C(=CC(=CC=2)C(F)(F)F)Cl)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 JBTRPWAZKNCNCE-DEOSSOPVSA-N 0.000 description 1
- QAZNPCKENXZTRX-YYMSGCCCSA-N benzyl n-[4-[(3s)-9-[2-methyl-3-(4-propan-2-ylphenyl)propyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC(C)CC=3C=CC(=CC=3)C(C)C)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 QAZNPCKENXZTRX-YYMSGCCCSA-N 0.000 description 1
- UGZFNELZTKVHCY-MHZLTWQESA-N benzyl n-[4-[(3s)-9-[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2C(=NOC=2C)C=2C(=CC=CC=2)Cl)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 UGZFNELZTKVHCY-MHZLTWQESA-N 0.000 description 1
- ZZQBEIOUSVZSCI-CJEZNJPTSA-N benzyl n-[4-[(3s)-9-[3-[4-(2,2-dimethylpropyl)phenyl]-2-methylpropyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC(C)CC=3C=CC(CC(C)(C)C)=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 ZZQBEIOUSVZSCI-CJEZNJPTSA-N 0.000 description 1
- LCXPJFHKPWOUAO-MHZLTWQESA-N benzyl n-[4-[(3s)-9-[4-(dimethylamino)benzoyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2C=CC(=CC=2)N(C)C)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 LCXPJFHKPWOUAO-MHZLTWQESA-N 0.000 description 1
- PPROSALWMOQRDZ-MHZLTWQESA-N benzyl n-[4-[(3s)-9-[5-(benzenesulfonyl)thiophen-2-yl]sulfonyl-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)S(=O)(=O)C=2SC(=CC=2)S(=O)(=O)C=2C=CC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 PPROSALWMOQRDZ-MHZLTWQESA-N 0.000 description 1
- HEOXBNBMYOGELE-PMERELPUSA-N benzyl n-[4-[(3s)-9-[[2,6-di(propan-2-yl)phenyl]carbamoyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C(=CC=CC=2C(C)C)C(C)C)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 HEOXBNBMYOGELE-PMERELPUSA-N 0.000 description 1
- FXUPRIRIQQHFGR-HKBQPEDESA-N benzyl n-[4-[(3s)-9-[[2-(4-chlorophenyl)sulfanylphenyl]methyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C(=CC=CC=3)SC=3C=CC(Cl)=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 FXUPRIRIQQHFGR-HKBQPEDESA-N 0.000 description 1
- YNMSLIOGDCEJPF-DEOSSOPVSA-N benzyl n-[4-[(3s)-9-[[2-chloro-5-(trifluoromethyl)phenyl]carbamoyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)NC=2C(=CC=C(C=2)C(F)(F)F)Cl)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 YNMSLIOGDCEJPF-DEOSSOPVSA-N 0.000 description 1
- XJOHZYVKFHKBKN-LHEWISCISA-N benzyl n-[4-[(3s)-9-[[3,4-bis(phenylmethoxy)phenyl]methyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=C(OCC=4C=CC=CC=4)C(OCC=4C=CC=CC=4)=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 XJOHZYVKFHKBKN-LHEWISCISA-N 0.000 description 1
- HSJYELDCZKDQAU-RDFOUATCSA-N benzyl n-[4-[(3s)-9-[[4-(4-hydroxy-4-methylpentyl)cyclohex-3-en-1-yl]methyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC3CC=C(CCCC(C)(C)O)CC3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 HSJYELDCZKDQAU-RDFOUATCSA-N 0.000 description 1
- CQQUKNHNNGLBME-HKBQPEDESA-N benzyl n-[4-[(3s)-9-[[4-[3-(dimethylamino)propoxy]phenyl]methyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=CC(OCCCN(C)C)=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 CQQUKNHNNGLBME-HKBQPEDESA-N 0.000 description 1
- JRYUWRZWUJGDOS-VWLOTQADSA-N benzyl n-[4-[(3s)-9-[di(propan-2-yl)carbamoyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)N(C(C)C)C(C)C)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 JRYUWRZWUJGDOS-VWLOTQADSA-N 0.000 description 1
- JJZPINCZGBMIQD-NRFANRHFSA-N benzyl n-[4-[(3s)-9-acetyl-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(C)=O)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 JJZPINCZGBMIQD-NRFANRHFSA-N 0.000 description 1
- VEIBCVDZGBUUGR-VWLOTQADSA-N benzyl n-[4-[(3s)-9-benzoyl-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=O)C=2C=CC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 VEIBCVDZGBUUGR-VWLOTQADSA-N 0.000 description 1
- KZPLUXWZJZRMOT-SANMLTNESA-N benzyl n-[4-[(3s)-9-benzyl-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC=3C=CC=CC=3)CC2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 KZPLUXWZJZRMOT-SANMLTNESA-N 0.000 description 1
- WBVJFYWPTGWWIM-SANMLTNESA-N benzyl n-[4-[(3s)-9-benzylsulfonyl-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)S(=O)(=O)CC=2C=CC=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 WBVJFYWPTGWWIM-SANMLTNESA-N 0.000 description 1
- AOFNNSUSZFPXTH-QFIPXVFZSA-N benzyl n-[4-[(3s)-9-butanethioyl-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)C(=S)CCC)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 AOFNNSUSZFPXTH-QFIPXVFZSA-N 0.000 description 1
- DJRCKPMWLZPLEN-QHCPKHFHSA-N benzyl n-[4-[(3s)-9-butyl-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C1CN(CCCC)CCC21C(=O)N[C@@H](CCCCNC(=O)OCC=1C=CC=CC=1)C(=O)N2CCC DJRCKPMWLZPLEN-QHCPKHFHSA-N 0.000 description 1
- JZROJJPNKKQZOU-DEOSSOPVSA-N benzyl n-[4-[(3s)-9-hexanoyl-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C1CN(C(=O)CCCCC)CCC21C(=O)N[C@@H](CCCCNC(=O)OCC=1C=CC=CC=1)C(=O)N2CCC JZROJJPNKKQZOU-DEOSSOPVSA-N 0.000 description 1
- AKDYDPMVCXPFRA-FQEVSTJZSA-N benzyl n-[4-[(3s)-9-methylsulfonyl-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)S(C)(=O)=O)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 AKDYDPMVCXPFRA-FQEVSTJZSA-N 0.000 description 1
- ISNMVHRKDGFHEP-LJAQVGFWSA-N benzyl n-[4-[(3s)-9-naphthalen-2-ylsulfonyl-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)S(=O)(=O)C=2C=C3C=CC=CC3=CC=2)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 ISNMVHRKDGFHEP-LJAQVGFWSA-N 0.000 description 1
- JWOVFPMOSOPLCT-UHFFFAOYSA-N benzyl n-[4-[1-(1-benzylpyrrolidin-3-yl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1C2CN(CC=3C=CC=CC=3)CC2)=O)NC(=O)C1(CC1)CCN1CCC1=CC=CC=C1 JWOVFPMOSOPLCT-UHFFFAOYSA-N 0.000 description 1
- LXOIDYPYSUSMQO-UHFFFAOYSA-N benzyl n-[4-[1-(1-benzylpyrrolidin-3-yl)-2,5-dioxo-9-(3-phenylpropyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1C2CN(CC=3C=CC=CC=3)CC2)=O)NC(=O)C1(CC1)CCN1CCCC1=CC=CC=C1 LXOIDYPYSUSMQO-UHFFFAOYSA-N 0.000 description 1
- LSIJUMFXLXWAQJ-UHFFFAOYSA-N benzyl n-[4-[1-(1-benzylpyrrolidin-3-yl)-2,5-dioxo-9-(4-phenylbutyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1C2CN(CC=3C=CC=CC=3)CC2)=O)NC(=O)C1(CC1)CCN1CCCCC1=CC=CC=C1 LSIJUMFXLXWAQJ-UHFFFAOYSA-N 0.000 description 1
- FHGKYKBZLSHGPU-UHFFFAOYSA-N benzyl n-[4-[1-(1-benzylpyrrolidin-3-yl)-2,5-dioxo-9-(5-phenylpentyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1C2CN(CC=3C=CC=CC=3)CC2)=O)NC(=O)C1(CC1)CCN1CCCCCC1=CC=CC=C1 FHGKYKBZLSHGPU-UHFFFAOYSA-N 0.000 description 1
- UQJPAHGUOICNAC-UHFFFAOYSA-N benzyl n-[4-[1-(1-benzylpyrrolidin-3-yl)-2,5-dioxo-9-(6-phenylhexyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1C2CN(CC=3C=CC=CC=3)CC2)=O)NC(=O)C1(CC1)CCN1CCCCCCC1=CC=CC=C1 UQJPAHGUOICNAC-UHFFFAOYSA-N 0.000 description 1
- ZKQFUVRCNUCSGQ-UHFFFAOYSA-N benzyl n-[4-[1-(1-benzylpyrrolidin-3-yl)-2,5-dioxo-9-phenyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1C2CN(CC=3C=CC=CC=3)CC2)=O)NC(=O)C1(CC1)CCN1C1=CC=CC=C1 ZKQFUVRCNUCSGQ-UHFFFAOYSA-N 0.000 description 1
- RVIDZEPPTANIFL-UHFFFAOYSA-N benzyl n-[4-[1-(1-benzylpyrrolidin-3-yl)-9-methyl-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C1CN(C)CCC21C(=O)NC(CCCCNC(=O)OCC=1C=CC=CC=1)C(=O)N2C1CN(CC=2C=CC=CC=2)CC1 RVIDZEPPTANIFL-UHFFFAOYSA-N 0.000 description 1
- LLRKVRIPTDRVHF-UHFFFAOYSA-N benzyl n-[4-[1-(2,2-diphenylethyl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=O)NC(=O)C1(CC1)CCN1CCC1=CC=CC=C1 LLRKVRIPTDRVHF-UHFFFAOYSA-N 0.000 description 1
- UMJZXWHAHUERFQ-UHFFFAOYSA-N benzyl n-[4-[1-(2,2-diphenylethyl)-2,5-dioxo-9-(3-phenylpropyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=O)NC(=O)C1(CC1)CCN1CCCC1=CC=CC=C1 UMJZXWHAHUERFQ-UHFFFAOYSA-N 0.000 description 1
- UGAWOMOOGNCATN-UHFFFAOYSA-N benzyl n-[4-[1-(2,2-diphenylethyl)-2,5-dioxo-9-(4-phenylbutyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=O)NC(=O)C1(CC1)CCN1CCCCC1=CC=CC=C1 UGAWOMOOGNCATN-UHFFFAOYSA-N 0.000 description 1
- BLXIYAVCBITNIA-UHFFFAOYSA-N benzyl n-[4-[1-(2,2-diphenylethyl)-2,5-dioxo-9-(5-phenylpentyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=O)NC(=O)C1(CC1)CCN1CCCCCC1=CC=CC=C1 BLXIYAVCBITNIA-UHFFFAOYSA-N 0.000 description 1
- DPZITDICZLHQGB-UHFFFAOYSA-N benzyl n-[4-[1-(2,2-diphenylethyl)-2,5-dioxo-9-(6-phenylhexyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=O)NC(=O)C1(CC1)CCN1CCCCCCC1=CC=CC=C1 DPZITDICZLHQGB-UHFFFAOYSA-N 0.000 description 1
- QNNPIDSZVIIEPP-UHFFFAOYSA-N benzyl n-[4-[1-(2,2-diphenylethyl)-2,5-dioxo-9-phenyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=O)NC(=O)C1(CC1)CCN1C1=CC=CC=C1 QNNPIDSZVIIEPP-UHFFFAOYSA-N 0.000 description 1
- USGMZPZTNNPYMT-UHFFFAOYSA-N benzyl n-[4-[1-(2,2-diphenylethyl)-9-methyl-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C1CN(C)CCC21C(=O)NC(CCCCNC(=O)OCC=1C=CC=CC=1)C(=O)N2CC(C=1C=CC=CC=1)C1=CC=CC=C1 USGMZPZTNNPYMT-UHFFFAOYSA-N 0.000 description 1
- ZKFHHJLWGDKMPL-UHFFFAOYSA-N benzyl n-[4-[1-(furan-2-ylmethyl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CC=2OC=CC=2)=O)NC(=O)C1(CC1)CCN1CCC1=CC=CC=C1 ZKFHHJLWGDKMPL-UHFFFAOYSA-N 0.000 description 1
- KMZBRFQYBRLGNC-UHFFFAOYSA-N benzyl n-[4-[1-(furan-2-ylmethyl)-2,5-dioxo-9-(3-phenylpropyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CC=2OC=CC=2)=O)NC(=O)C1(CC1)CCN1CCCC1=CC=CC=C1 KMZBRFQYBRLGNC-UHFFFAOYSA-N 0.000 description 1
- UAHHFZNHRNBWTA-UHFFFAOYSA-N benzyl n-[4-[1-(furan-2-ylmethyl)-2,5-dioxo-9-(4-phenylbutyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CC=2OC=CC=2)=O)NC(=O)C1(CC1)CCN1CCCCC1=CC=CC=C1 UAHHFZNHRNBWTA-UHFFFAOYSA-N 0.000 description 1
- QZOBPWBLKGJGMG-UHFFFAOYSA-N benzyl n-[4-[1-[2-(1h-indol-3-yl)ethyl]-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CCC=2C3=CC=CC=C3NC=2)=O)NC(=O)C1(CC1)CCN1CCC1=CC=CC=C1 QZOBPWBLKGJGMG-UHFFFAOYSA-N 0.000 description 1
- BTGQGPLGLUQURJ-UHFFFAOYSA-N benzyl n-[4-[1-[2-(1h-indol-3-yl)ethyl]-2,5-dioxo-9-(3-phenylpropyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CCC=2C3=CC=CC=C3NC=2)=O)NC(=O)C1(CC1)CCN1CCCC1=CC=CC=C1 BTGQGPLGLUQURJ-UHFFFAOYSA-N 0.000 description 1
- VBUGATVZAAAADB-UHFFFAOYSA-N benzyl n-[4-[1-[2-(1h-indol-3-yl)ethyl]-2,5-dioxo-9-(4-phenylbutyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CCC=2C3=CC=CC=C3NC=2)=O)NC(=O)C1(CC1)CCN1CCCCC1=CC=CC=C1 VBUGATVZAAAADB-UHFFFAOYSA-N 0.000 description 1
- WLAZNHRDLNQBEG-UHFFFAOYSA-N benzyl n-[4-[1-[2-(1h-indol-3-yl)ethyl]-2,5-dioxo-9-(5-phenylpentyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CCC=2C3=CC=CC=C3NC=2)=O)NC(=O)C1(CC1)CCN1CCCCCC1=CC=CC=C1 WLAZNHRDLNQBEG-UHFFFAOYSA-N 0.000 description 1
- BBZZUBFNKBLKSI-UHFFFAOYSA-N benzyl n-[4-[1-[2-(1h-indol-3-yl)ethyl]-2,5-dioxo-9-(6-phenylhexyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CCC=2C3=CC=CC=C3NC=2)=O)NC(=O)C1(CC1)CCN1CCCCCCC1=CC=CC=C1 BBZZUBFNKBLKSI-UHFFFAOYSA-N 0.000 description 1
- XPCGTHYEJGZGFF-UHFFFAOYSA-N benzyl n-[4-[1-[2-(1h-indol-3-yl)ethyl]-2,5-dioxo-9-phenyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CCC=2C3=CC=CC=C3NC=2)=O)NC(=O)C1(CC1)CCN1C1=CC=CC=C1 XPCGTHYEJGZGFF-UHFFFAOYSA-N 0.000 description 1
- DHSWPDOFIXRUOM-UHFFFAOYSA-N benzyl n-[4-[1-[2-(1h-indol-3-yl)ethyl]-9-methyl-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C1CN(C)CCC21C(=O)NC(CCCCNC(=O)OCC=1C=CC=CC=1)C(=O)N2CCC1=CNC2=CC=CC=C12 DHSWPDOFIXRUOM-UHFFFAOYSA-N 0.000 description 1
- BERMBUXMOKXCRD-UHFFFAOYSA-N benzyl n-[4-[1-benzyl-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CC=2C=CC=CC=2)=O)NC(=O)C1(CC1)CCN1CCC1=CC=CC=C1 BERMBUXMOKXCRD-UHFFFAOYSA-N 0.000 description 1
- CJHVBMZDVDFAPU-UHFFFAOYSA-N benzyl n-[4-[1-benzyl-2,5-dioxo-9-(3-phenylpropyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CC=2C=CC=CC=2)=O)NC(=O)C1(CC1)CCN1CCCC1=CC=CC=C1 CJHVBMZDVDFAPU-UHFFFAOYSA-N 0.000 description 1
- DWQIXRJWRVVTMO-UHFFFAOYSA-N benzyl n-[4-[1-benzyl-2,5-dioxo-9-(4-phenylbutyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CC=2C=CC=CC=2)=O)NC(=O)C1(CC1)CCN1CCCCC1=CC=CC=C1 DWQIXRJWRVVTMO-UHFFFAOYSA-N 0.000 description 1
- BVJZNPJJRYJKED-UHFFFAOYSA-N benzyl n-[4-[1-benzyl-2,5-dioxo-9-(5-phenylpentyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CC=2C=CC=CC=2)=O)NC(=O)C1(CC1)CCN1CCCCCC1=CC=CC=C1 BVJZNPJJRYJKED-UHFFFAOYSA-N 0.000 description 1
- OYXRTCXGVYLJKH-UHFFFAOYSA-N benzyl n-[4-[1-benzyl-2,5-dioxo-9-(6-phenylhexyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CC=2C=CC=CC=2)=O)NC(=O)C1(CC1)CCN1CCCCCCC1=CC=CC=C1 OYXRTCXGVYLJKH-UHFFFAOYSA-N 0.000 description 1
- YVUSIXYWHYKWEL-UHFFFAOYSA-N benzyl n-[4-[2,5-dioxo-1,9-bis(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CCC=2C=CC=CC=2)=O)NC(=O)C1(CC1)CCN1CCC1=CC=CC=C1 YVUSIXYWHYKWEL-UHFFFAOYSA-N 0.000 description 1
- XBEPUIPGHJNHGD-UHFFFAOYSA-N benzyl n-[4-[2,5-dioxo-1-(2-phenylethyl)-9-(3-phenylpropyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CCC=2C=CC=CC=2)=O)NC(=O)C1(CC1)CCN1CCCC1=CC=CC=C1 XBEPUIPGHJNHGD-UHFFFAOYSA-N 0.000 description 1
- JDNOTHMJCSNSNQ-UHFFFAOYSA-N benzyl n-[4-[2,5-dioxo-1-(2-phenylethyl)-9-(5-phenylpentyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CCC=2C=CC=CC=2)=O)NC(=O)C1(CC1)CCN1CCCCCC1=CC=CC=C1 JDNOTHMJCSNSNQ-UHFFFAOYSA-N 0.000 description 1
- QXVAJRMWJVOLBZ-UHFFFAOYSA-N benzyl n-[4-[2,5-dioxo-1-(2-phenylethyl)-9-(6-phenylhexyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CCC=2C=CC=CC=2)=O)NC(=O)C1(CC1)CCN1CCCCCCC1=CC=CC=C1 QXVAJRMWJVOLBZ-UHFFFAOYSA-N 0.000 description 1
- DFFOJCSBHFVQDC-UHFFFAOYSA-N benzyl n-[4-[2,5-dioxo-1-(oxolan-2-ylmethyl)-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CC2OCCC2)=O)NC(=O)C1(CC1)CCN1CCC1=CC=CC=C1 DFFOJCSBHFVQDC-UHFFFAOYSA-N 0.000 description 1
- JNHGPJQFTPQZIZ-UHFFFAOYSA-N benzyl n-[4-[2,5-dioxo-1-(oxolan-2-ylmethyl)-9-(3-phenylpropyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CC2OCCC2)=O)NC(=O)C1(CC1)CCN1CCCC1=CC=CC=C1 JNHGPJQFTPQZIZ-UHFFFAOYSA-N 0.000 description 1
- SCPITLYEDWLDCU-UHFFFAOYSA-N benzyl n-[4-[2,5-dioxo-1-(oxolan-2-ylmethyl)-9-(4-phenylbutyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CC2OCCC2)=O)NC(=O)C1(CC1)CCN1CCCCC1=CC=CC=C1 SCPITLYEDWLDCU-UHFFFAOYSA-N 0.000 description 1
- DEOFINBAUVOKHU-UHFFFAOYSA-N benzyl n-[4-[2,5-dioxo-1-(oxolan-2-ylmethyl)-9-(5-phenylpentyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CC2OCCC2)=O)NC(=O)C1(CC1)CCN1CCCCCC1=CC=CC=C1 DEOFINBAUVOKHU-UHFFFAOYSA-N 0.000 description 1
- MUPRCMZYPSTIHN-UHFFFAOYSA-N benzyl n-[4-[2,5-dioxo-1-(oxolan-2-ylmethyl)-9-(6-phenylhexyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CC2OCCC2)=O)NC(=O)C1(CC1)CCN1CCCCCCC1=CC=CC=C1 MUPRCMZYPSTIHN-UHFFFAOYSA-N 0.000 description 1
- WPHCKUKIWVIFJO-UHFFFAOYSA-N benzyl n-[4-[2,5-dioxo-1-(oxolan-2-ylmethyl)-9-phenyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CC2OCCC2)=O)NC(=O)C1(CC1)CCN1C1=CC=CC=C1 WPHCKUKIWVIFJO-UHFFFAOYSA-N 0.000 description 1
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- PPWZDTNZIKBLIC-UHFFFAOYSA-N benzyl n-[4-[2,5-dioxo-9-(4-phenylbutyl)-1-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CCC=2C=CC=CC=2)=O)NC(=O)C1(CC1)CCN1CCCCC1=CC=CC=C1 PPWZDTNZIKBLIC-UHFFFAOYSA-N 0.000 description 1
- VUGRMGPEWOYHQY-UHFFFAOYSA-N benzyl n-[4-[2,5-dioxo-9-(4-phenylbutyl)-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N1C(=O)C2(CCN(CCCCC=3C=CC=CC=3)CC2)N(CCC)C(=O)C1CCCCNC(=O)OCC1=CC=CC=C1 VUGRMGPEWOYHQY-UHFFFAOYSA-N 0.000 description 1
- UGNIOHPTQDAYER-UHFFFAOYSA-N benzyl n-[4-[2,5-dioxo-9-(5-phenylpentyl)-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N1C(=O)C2(CCN(CCCCCC=3C=CC=CC=3)CC2)N(CCC)C(=O)C1CCCCNC(=O)OCC1=CC=CC=C1 UGNIOHPTQDAYER-UHFFFAOYSA-N 0.000 description 1
- QVOORWZNVSALRI-UHFFFAOYSA-N benzyl n-[4-[2,5-dioxo-9-(6-phenylhexyl)-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound N1C(=O)C2(CCN(CCCCCCC=3C=CC=CC=3)CC2)N(CCC)C(=O)C1CCCCNC(=O)OCC1=CC=CC=C1 QVOORWZNVSALRI-UHFFFAOYSA-N 0.000 description 1
- UIZVQANXXIZYLX-UHFFFAOYSA-N benzyl n-[4-[2,5-dioxo-9-phenyl-1-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CCC=2C=CC=CC=2)=O)NC(=O)C1(CC1)CCN1C1=CC=CC=C1 UIZVQANXXIZYLX-UHFFFAOYSA-N 0.000 description 1
- WGCHTDHHSKNCSD-UHFFFAOYSA-N benzyl n-[4-[9-benzyl-1-(1-benzylpyrrolidin-3-yl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1C2CN(CC=3C=CC=CC=3)CC2)=O)NC(=O)C1(CC1)CCN1CC1=CC=CC=C1 WGCHTDHHSKNCSD-UHFFFAOYSA-N 0.000 description 1
- GYEDTXIYBZTEHY-UHFFFAOYSA-N benzyl n-[4-[9-benzyl-1-(2,2-diphenylethyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCCC(C(N1CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=O)NC(=O)C1(CC1)CCN1CC1=CC=CC=C1 GYEDTXIYBZTEHY-UHFFFAOYSA-N 0.000 description 1
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- RCFMPABSLBMQJA-UHFFFAOYSA-N benzyl n-[4-[9-methyl-2,5-dioxo-1-(oxolan-2-ylmethyl)-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound C1CN(C)CCC21C(=O)NC(CCCCNC(=O)OCC=1C=CC=CC=1)C(=O)N2CC1OCCC1 RCFMPABSLBMQJA-UHFFFAOYSA-N 0.000 description 1
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- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
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- 125000002960 margaryl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- DJGAAPFSPWAYTJ-UHFFFAOYSA-M metamizole sodium Chemical compound [Na+].O=C1C(N(CS([O-])(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 DJGAAPFSPWAYTJ-UHFFFAOYSA-M 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- DZNKOAWEHDKBEP-UHFFFAOYSA-N methyl 2-[6-[bis(2-methoxy-2-oxoethyl)amino]-5-[2-[2-[bis(2-methoxy-2-oxoethyl)amino]-5-methylphenoxy]ethoxy]-1-benzofuran-2-yl]-1,3-oxazole-5-carboxylate Chemical compound COC(=O)CN(CC(=O)OC)C1=CC=C(C)C=C1OCCOC(C(=C1)N(CC(=O)OC)CC(=O)OC)=CC2=C1OC(C=1OC(=CN=1)C(=O)OC)=C2 DZNKOAWEHDKBEP-UHFFFAOYSA-N 0.000 description 1
- QXAGXOGSJACQQF-VWLOTQADSA-N methyl 2-[[(3s)-2,5-dioxo-3-[4-(phenylmethoxycarbonylamino)butyl]-1-propyl-1,4,9-triazaspiro[5.5]undecan-9-yl]sulfonyl]benzoate Chemical compound C([C@H]1C(=O)N(C2(CCN(CC2)S(=O)(=O)C=2C(=CC=CC=2)C(=O)OC)C(=O)N1)CCC)CCCNC(=O)OCC1=CC=CC=C1 QXAGXOGSJACQQF-VWLOTQADSA-N 0.000 description 1
- DJNOJHBQNTWHKX-UHFFFAOYSA-N methyl 2-[[3-(2-methylpropyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-9-yl]sulfonyl]benzoate Chemical compound CCCN1C(=O)C(CC(C)C)NC(=O)C11CCN(S(=O)(=O)C=2C(=CC=CC=2)C(=O)OC)CC1 DJNOJHBQNTWHKX-UHFFFAOYSA-N 0.000 description 1
- XDLXWACDNPOORU-UHFFFAOYSA-N methyl 3-[[1-benzyl-3-(cyclohexylmethyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]-1h-indole-6-carboxylate Chemical compound C=1NC2=CC(C(=O)OC)=CC=C2C=1CN(CC1)CCC1(C(NC(CC1CCCCC1)C1=O)=O)N1CC1=CC=CC=C1 XDLXWACDNPOORU-UHFFFAOYSA-N 0.000 description 1
- ZFLMZEYVGNFDTB-UHFFFAOYSA-N methyl 3-[[1-butyl-3-(2-methylpropyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]-1h-indole-6-carboxylate Chemical compound CCCCN1C(=O)C(CC(C)C)NC(=O)C11CCN(CC=2C3=CC=C(C=C3NC=2)C(=O)OC)CC1 ZFLMZEYVGNFDTB-UHFFFAOYSA-N 0.000 description 1
- FVJGELPCLZAGRZ-UHFFFAOYSA-N methyl 3-[[1-butyl-3-(cyclohexylmethyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]-1h-indole-6-carboxylate Chemical compound N1C(=O)C2(CCN(CC=3C4=CC=C(C=C4NC=3)C(=O)OC)CC2)N(CCCC)C(=O)C1CC1CCCCC1 FVJGELPCLZAGRZ-UHFFFAOYSA-N 0.000 description 1
- IVFICWPCPNFVQB-UHFFFAOYSA-N methyl 3-[[1-ethyl-3-(2-methylpropyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]-1h-indole-6-carboxylate Chemical compound CCN1C(=O)C(CC(C)C)NC(=O)C11CCN(CC=2C3=CC=C(C=C3NC=2)C(=O)OC)CC1 IVFICWPCPNFVQB-UHFFFAOYSA-N 0.000 description 1
- DYZAGZLTHNYXIZ-UHFFFAOYSA-N methyl 3-[[3-(2-methylpropyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]-1h-indole-6-carboxylate Chemical compound CCCN1C(=O)C(CC(C)C)NC(=O)C11CCN(CC=2C3=CC=C(C=C3NC=2)C(=O)OC)CC1 DYZAGZLTHNYXIZ-UHFFFAOYSA-N 0.000 description 1
- OOGPZIUTLGXRSK-UHFFFAOYSA-N methyl 3-[[3-(cyclohexylmethyl)-1-(2-methoxyethyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]-1h-indole-6-carboxylate Chemical compound N1C(=O)C2(CCN(CC=3C4=CC=C(C=C4NC=3)C(=O)OC)CC2)N(CCOC)C(=O)C1CC1CCCCC1 OOGPZIUTLGXRSK-UHFFFAOYSA-N 0.000 description 1
- IBEFYRRTJYXCSL-UHFFFAOYSA-N methyl 3-[[3-(cyclohexylmethyl)-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]-1h-indole-6-carboxylate Chemical compound N1C(=O)C2(CCN(CC=3C4=CC=C(C=C4NC=3)C(=O)OC)CC2)N(CCC)C(=O)C1CC1CCCCC1 IBEFYRRTJYXCSL-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
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- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
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- RPBYTSAAWWWHGR-UHFFFAOYSA-N tert-butyl 3-[2,5-dioxo-3-(phenylmethoxymethyl)-9-(5-phenylpentyl)-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound N1C(=O)C2(CCN(CCCCCC=3C=CC=CC=3)CC2)N(CCC(=O)OC(C)(C)C)C(=O)C1COCC1=CC=CC=C1 RPBYTSAAWWWHGR-UHFFFAOYSA-N 0.000 description 1
- QGHIUGRWOUWOCK-UHFFFAOYSA-N tert-butyl 3-[2,5-dioxo-3-[4-(phenylmethoxycarbonylamino)butyl]-9-(5-phenylpentyl)-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound N1C(=O)C2(CCN(CCCCCC=3C=CC=CC=3)CC2)N(CCC(=O)OC(C)(C)C)C(=O)C1CCCCNC(=O)OCC1=CC=CC=C1 QGHIUGRWOUWOCK-UHFFFAOYSA-N 0.000 description 1
- KTVMMBXEUQJEKK-UHFFFAOYSA-N tert-butyl 3-[2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound CC(C)(C)OC(=O)CCN1C(=O)CNC(=O)C11CCN(CCC=2C=CC=CC=2)CC1 KTVMMBXEUQJEKK-UHFFFAOYSA-N 0.000 description 1
- ZTSLAGSVBJIXPO-UHFFFAOYSA-N tert-butyl 3-[2,5-dioxo-9-(2-phenylethyl)-3-(phenylmethoxymethyl)-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound N1C(=O)C2(CCN(CCC=3C=CC=CC=3)CC2)N(CCC(=O)OC(C)(C)C)C(=O)C1COCC1=CC=CC=C1 ZTSLAGSVBJIXPO-UHFFFAOYSA-N 0.000 description 1
- CUHVWXCTFCFXTN-UHFFFAOYSA-N tert-butyl 3-[2,5-dioxo-9-(2-phenylethyl)-3-[4-(phenylmethoxycarbonylamino)butyl]-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound N1C(=O)C2(CCN(CCC=3C=CC=CC=3)CC2)N(CCC(=O)OC(C)(C)C)C(=O)C1CCCCNC(=O)OCC1=CC=CC=C1 CUHVWXCTFCFXTN-UHFFFAOYSA-N 0.000 description 1
- QWGUGGVCAKQYNY-UHFFFAOYSA-N tert-butyl 3-[2,5-dioxo-9-(3-phenylpropyl)-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound CC(C)(C)OC(=O)CCN1C(=O)CNC(=O)C11CCN(CCCC=2C=CC=CC=2)CC1 QWGUGGVCAKQYNY-UHFFFAOYSA-N 0.000 description 1
- MMHLXVKBOGVAAP-UHFFFAOYSA-N tert-butyl 3-[2,5-dioxo-9-(4-phenylbutyl)-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound CC(C)(C)OC(=O)CCN1C(=O)CNC(=O)C11CCN(CCCCC=2C=CC=CC=2)CC1 MMHLXVKBOGVAAP-UHFFFAOYSA-N 0.000 description 1
- VQQRUWMBVSICPH-UHFFFAOYSA-N tert-butyl 3-[2,5-dioxo-9-(4-phenylbutyl)-3-(phenylmethoxymethyl)-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound N1C(=O)C2(CCN(CCCCC=3C=CC=CC=3)CC2)N(CCC(=O)OC(C)(C)C)C(=O)C1COCC1=CC=CC=C1 VQQRUWMBVSICPH-UHFFFAOYSA-N 0.000 description 1
- TUUQZTZASYAKHK-UHFFFAOYSA-N tert-butyl 3-[2,5-dioxo-9-(4-phenylbutyl)-3-[4-(phenylmethoxycarbonylamino)butyl]-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound N1C(=O)C2(CCN(CCCCC=3C=CC=CC=3)CC2)N(CCC(=O)OC(C)(C)C)C(=O)C1CCCCNC(=O)OCC1=CC=CC=C1 TUUQZTZASYAKHK-UHFFFAOYSA-N 0.000 description 1
- DOASMULKEJWAAU-UHFFFAOYSA-N tert-butyl 3-[2,5-dioxo-9-(5-phenylpentyl)-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound CC(C)(C)OC(=O)CCN1C(=O)CNC(=O)C11CCN(CCCCCC=2C=CC=CC=2)CC1 DOASMULKEJWAAU-UHFFFAOYSA-N 0.000 description 1
- ZLYOZKCNQLXHGZ-UHFFFAOYSA-N tert-butyl 3-[2,5-dioxo-9-(6-phenylhexyl)-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound CC(C)(C)OC(=O)CCN1C(=O)CNC(=O)C11CCN(CCCCCCC=2C=CC=CC=2)CC1 ZLYOZKCNQLXHGZ-UHFFFAOYSA-N 0.000 description 1
- GQVFPYYFVBWBDZ-UHFFFAOYSA-N tert-butyl 3-[2,5-dioxo-9-(6-phenylhexyl)-3-(phenylmethoxymethyl)-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound N1C(=O)C2(CCN(CCCCCCC=3C=CC=CC=3)CC2)N(CCC(=O)OC(C)(C)C)C(=O)C1COCC1=CC=CC=C1 GQVFPYYFVBWBDZ-UHFFFAOYSA-N 0.000 description 1
- SVHGVIPJAXCCSM-UHFFFAOYSA-N tert-butyl 3-[2,5-dioxo-9-(6-phenylhexyl)-3-[4-(phenylmethoxycarbonylamino)butyl]-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound N1C(=O)C2(CCN(CCCCCCC=3C=CC=CC=3)CC2)N(CCC(=O)OC(C)(C)C)C(=O)C1CCCCNC(=O)OCC1=CC=CC=C1 SVHGVIPJAXCCSM-UHFFFAOYSA-N 0.000 description 1
- WSNWYJUSKMJNLE-UHFFFAOYSA-N tert-butyl 3-[2,5-dioxo-9-phenyl-3-[4-(phenylmethoxycarbonylamino)butyl]-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound N1C(=O)C2(CCN(CC2)C=2C=CC=CC=2)N(CCC(=O)OC(C)(C)C)C(=O)C1CCCCNC(=O)OCC1=CC=CC=C1 WSNWYJUSKMJNLE-UHFFFAOYSA-N 0.000 description 1
- VRVYORAVHZOIMS-UHFFFAOYSA-N tert-butyl 3-[3-(1h-indol-3-ylmethyl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound CC(C)(C)OC(=O)CCN1C(=O)C(CC=2C3=CC=CC=C3NC=2)NC(=O)C1(CC1)CCN1CCC1=CC=CC=C1 VRVYORAVHZOIMS-UHFFFAOYSA-N 0.000 description 1
- UYMITLVAFVHABN-UHFFFAOYSA-N tert-butyl 3-[3-(1h-indol-3-ylmethyl)-2,5-dioxo-9-(3-phenylpropyl)-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound CC(C)(C)OC(=O)CCN1C(=O)C(CC=2C3=CC=CC=C3NC=2)NC(=O)C1(CC1)CCN1CCCC1=CC=CC=C1 UYMITLVAFVHABN-UHFFFAOYSA-N 0.000 description 1
- VENWHVQFYOYJMX-UHFFFAOYSA-N tert-butyl 3-[3-(1h-indol-3-ylmethyl)-2,5-dioxo-9-(4-phenylbutyl)-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound CC(C)(C)OC(=O)CCN1C(=O)C(CC=2C3=CC=CC=C3NC=2)NC(=O)C1(CC1)CCN1CCCCC1=CC=CC=C1 VENWHVQFYOYJMX-UHFFFAOYSA-N 0.000 description 1
- KEIWRBAXXGBNJV-UHFFFAOYSA-N tert-butyl 3-[3-(1h-indol-3-ylmethyl)-2,5-dioxo-9-(5-phenylpentyl)-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound CC(C)(C)OC(=O)CCN1C(=O)C(CC=2C3=CC=CC=C3NC=2)NC(=O)C1(CC1)CCN1CCCCCC1=CC=CC=C1 KEIWRBAXXGBNJV-UHFFFAOYSA-N 0.000 description 1
- AUBFCRXBICKQSN-UHFFFAOYSA-N tert-butyl 3-[3-(1h-indol-3-ylmethyl)-2,5-dioxo-9-(6-phenylhexyl)-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound CC(C)(C)OC(=O)CCN1C(=O)C(CC=2C3=CC=CC=C3NC=2)NC(=O)C1(CC1)CCN1CCCCCCC1=CC=CC=C1 AUBFCRXBICKQSN-UHFFFAOYSA-N 0.000 description 1
- OOBIFTICSXPBLB-UHFFFAOYSA-N tert-butyl 3-[3-(1h-indol-3-ylmethyl)-2,5-dioxo-9-phenyl-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound CC(C)(C)OC(=O)CCN1C(=O)C(CC=2C3=CC=CC=C3NC=2)NC(=O)C1(CC1)CCN1C1=CC=CC=C1 OOBIFTICSXPBLB-UHFFFAOYSA-N 0.000 description 1
- HCUUCPSQMQQOCO-UHFFFAOYSA-N tert-butyl 3-[3-(1h-indol-3-ylmethyl)-9-methyl-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound C1CN(C)CCC21C(=O)NC(CC=1C3=CC=CC=C3NC=1)C(=O)N2CCC(=O)OC(C)(C)C HCUUCPSQMQQOCO-UHFFFAOYSA-N 0.000 description 1
- JQJFSHWKWAGQQJ-UHFFFAOYSA-N tert-butyl 3-[3-(2-methylpropyl)-2,5-dioxo-9-(2-phenylethyl)-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound CC(C)(C)OC(=O)CCN1C(=O)C(CC(C)C)NC(=O)C11CCN(CCC=2C=CC=CC=2)CC1 JQJFSHWKWAGQQJ-UHFFFAOYSA-N 0.000 description 1
- PNHSUVSFPYVEJR-UHFFFAOYSA-N tert-butyl 3-[3-(2-methylpropyl)-2,5-dioxo-9-(3-phenylpropyl)-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound CC(C)(C)OC(=O)CCN1C(=O)C(CC(C)C)NC(=O)C11CCN(CCCC=2C=CC=CC=2)CC1 PNHSUVSFPYVEJR-UHFFFAOYSA-N 0.000 description 1
- CMNXLHRPNAYBBC-UHFFFAOYSA-N tert-butyl 3-[3-(2-methylpropyl)-2,5-dioxo-9-(4-phenylbutyl)-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound CC(C)(C)OC(=O)CCN1C(=O)C(CC(C)C)NC(=O)C11CCN(CCCCC=2C=CC=CC=2)CC1 CMNXLHRPNAYBBC-UHFFFAOYSA-N 0.000 description 1
- QTLWYJQNKIBDIJ-UHFFFAOYSA-N tert-butyl 3-[3-(2-methylpropyl)-2,5-dioxo-9-(5-phenylpentyl)-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound CC(C)(C)OC(=O)CCN1C(=O)C(CC(C)C)NC(=O)C11CCN(CCCCCC=2C=CC=CC=2)CC1 QTLWYJQNKIBDIJ-UHFFFAOYSA-N 0.000 description 1
- DWYNPXILZQOGOZ-UHFFFAOYSA-N tert-butyl 3-[3-(2-methylpropyl)-2,5-dioxo-9-(6-phenylhexyl)-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound CC(C)(C)OC(=O)CCN1C(=O)C(CC(C)C)NC(=O)C11CCN(CCCCCCC=2C=CC=CC=2)CC1 DWYNPXILZQOGOZ-UHFFFAOYSA-N 0.000 description 1
- KQYSSOMGMJERFZ-UHFFFAOYSA-N tert-butyl 3-[3-(2-methylpropyl)-2,5-dioxo-9-phenyl-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound CC(C)(C)OC(=O)CCN1C(=O)C(CC(C)C)NC(=O)C11CCN(C=2C=CC=CC=2)CC1 KQYSSOMGMJERFZ-UHFFFAOYSA-N 0.000 description 1
- LCEKRWZDXOIOSC-UHFFFAOYSA-N tert-butyl 3-[9-benzyl-2,5-dioxo-3-(2-oxo-2-phenylmethoxyethyl)-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound N1C(=O)C2(CCN(CC=3C=CC=CC=3)CC2)N(CCC(=O)OC(C)(C)C)C(=O)C1CC(=O)OCC1=CC=CC=C1 LCEKRWZDXOIOSC-UHFFFAOYSA-N 0.000 description 1
- YQEFKENWXZFGPV-UHFFFAOYSA-N tert-butyl 3-[9-benzyl-2,5-dioxo-3-[4-(phenylmethoxycarbonylamino)butyl]-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound N1C(=O)C2(CCN(CC=3C=CC=CC=3)CC2)N(CCC(=O)OC(C)(C)C)C(=O)C1CCCCNC(=O)OCC1=CC=CC=C1 YQEFKENWXZFGPV-UHFFFAOYSA-N 0.000 description 1
- UMXHHSRFAZEPQH-UHFFFAOYSA-N tert-butyl 3-[9-benzyl-3-(1h-indol-3-ylmethyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound CC(C)(C)OC(=O)CCN1C(=O)C(CC=2C3=CC=CC=C3NC=2)NC(=O)C1(CC1)CCN1CC1=CC=CC=C1 UMXHHSRFAZEPQH-UHFFFAOYSA-N 0.000 description 1
- WGEGWEFSMBXSIL-UHFFFAOYSA-N tert-butyl 3-[9-benzyl-3-(2-methylpropyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound CC(C)(C)OC(=O)CCN1C(=O)C(CC(C)C)NC(=O)C11CCN(CC=2C=CC=CC=2)CC1 WGEGWEFSMBXSIL-UHFFFAOYSA-N 0.000 description 1
- YHFKSQJLISYRPF-UHFFFAOYSA-N tert-butyl 3-[9-methyl-2,5-dioxo-3-(2-oxo-2-phenylmethoxyethyl)-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound C1CN(C)CCC21C(=O)NC(CC(=O)OCC=1C=CC=CC=1)C(=O)N2CCC(=O)OC(C)(C)C YHFKSQJLISYRPF-UHFFFAOYSA-N 0.000 description 1
- QYXFIGPSOVDEKZ-UHFFFAOYSA-N tert-butyl 3-[9-methyl-2,5-dioxo-3-[4-(phenylmethoxycarbonylamino)butyl]-1,4,9-triazaspiro[5.5]undecan-1-yl]propanoate Chemical compound C1CN(C)CCC21C(=O)NC(CCCCNC(=O)OCC=1C=CC=CC=1)C(=O)N2CCC(=O)OC(C)(C)C QYXFIGPSOVDEKZ-UHFFFAOYSA-N 0.000 description 1
- ZIWNAJCPQZISSW-QHCPKHFHSA-N tert-butyl n-[4-[(3s)-2,5-dioxo-9-(2-phenylethyl)-1-propyl-1,4,9-triazaspiro[5.5]undecan-3-yl]butyl]carbamate Chemical compound CCCN1C(=O)[C@H](CCCCNC(=O)OC(C)(C)C)NC(=O)C11CCN(CCC=2C=CC=CC=2)CC1 ZIWNAJCPQZISSW-QHCPKHFHSA-N 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- RWXZKKKYLRFREK-UHFFFAOYSA-N thiadiazepane Chemical compound C1CCSNNC1 RWXZKKKYLRFREK-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
- 230000002992 thymic effect Effects 0.000 description 1
- 229960001402 tilidine Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 230000026683 transduction Effects 0.000 description 1
- 238000010361 transduction Methods 0.000 description 1
- 125000005040 tridecenyl group Chemical group C(=CCCCCCCCCCCC)* 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 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
- 150000003672 ureas Chemical class 0.000 description 1
- 210000003556 vascular endothelial cell Anatomy 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
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Abstract
본 발명은 하기 화학식 I로 표시되는 트리아자스피로[5. 5]운데칸 유도체, 이들의 4급 암모늄염, 이들의 N-옥사이드, 이들의 비독성염, 또는 그것을 유효성분으로서 함유하는 약제(식 중의 기호는 명세서에 기재한 바와 같음)를 제공하는 것을 목적으로 한다.
화학식 I
상기 화학식 I로 표시되는 화합물은 케모카인/케모카인 수용체의 작용을 제어하기 때문에, 각종 염증성 질환, 천식, 아토피성 피부염, 두드러기, 알레르기 질환, 신장염, 신장증, 간염, 관절염, 만성관절 류머티스 등의 예방 및/또는 치료에 유용하다.
Description
케모카인은 내인성의 백혈구 주화성, 활성화 작용을 가지며, 헤파린 결합성이 강한 염기성 단백질로서 알려져 있다. 현재, 케모카인은 염증, 면역 반응시의 특이적 백혈구의 침윤을 제어할 뿐만 아니라, 발생, 생리적 조건하에서의 림프구의귀소(homing), 혈구 전구 세포, 체세포의 이동에도 관계된다고 생각된다.
혈구 세포는 각종 시토킨에 의해 그 분화, 증식, 세포사멸이 제어되고 있다. 생체내에 있어서 염증은 국소적으로 보여지고, 림프구의 분화, 성숙 등은 어떤 특정한 부위에서 행해지고 있다. 즉, 필요로 하는 각종 세포가 어떤 특정한 부위로 이동하고, 집적하여 일련의 염증, 면역 반응이 일어난다. 따라서, 세포의 분화, 증식, 사멸에 덧붙여 세포의 이동도 면역계에 있어서 필요 불가결한 현상이다.
생체내에서의 혈구 세포의 이동은, 우선 발생 과정에 있어서 AGM 영역에서 시작되는 조혈이 태아의 간을 거쳐 골수에서의 영구 조혈로 이행함으로써 시작된다. 더욱이, 태아의 간, 골수로부터 흉선으로 T 세포, 흉선 수상(樹狀) 세포의 전구 세포가 이동하고, 흉선 환경하에서 세포 분화된다. 클론 선택을 받은 T 세포는 2차 림프 조직으로 이동하고, 말초에 있어서의 면역 반응에 관여한다. 항원을 포착하여 활성화, 분화된 피부의 랑겔 한스 세포는 국소 림프절의 T 세포 영역으로 이동하고, 수상 돌기 세포로서 미경험(naive) T 세포를 활성화한다. 메모리 T 세포는 림프관, 혈관을 거쳐 다시 림프절에 귀소한다. 또한, B 세포, 장관상피내 T 세포, γδT 세포, NKT 세포, 수상 세포는 골수에서 흉선을 거치지 않고서 이동, 분화되어 면역 반응에 관여한다.
케모카인은 이러한 각종 세포의 이동에 깊게 관여하고 있다. 예컨대, MIP3β, SLC와 그 수용체인 CCR7은 항원을 포착한 성숙 수상 세포가 미경험 T 세포 및 메모리 T 세포와 효율적으로 만나기 위해서, 이들 세포의 국소 림프 조직으로의 이동, 귀소에 있어서 중요한 작용을 하고 있다. SLC의 발현에 결손이 있는 PLT 마우스의 2차 림프절에는 항원 특이적인 면역 반응을 담당하기 위해서 필요한 T 세포 및 수상 세포가 거의 관찰되지 않는다(J. Exp. Med., 189 (3), 451(1999)).
MDC, TARC와 그 수용체인 CCR4는 Th2 세포가 관계된 면역, 염증 반응에 있어서, Th2 세포의 국소로의 이동에 중요한 작용을 하고 있다. 래트 극증 간염 모델(P.acnes+LPS)에 있어서, 항 TARC 항체는 혈중 ALT량의 상승 및 간장중 TNFα, FasL 발현량의 상승을 억제하고, 더욱이 래트 치사율을 개선하였다(J. Clin. Invest., 102 , 1933(1998)). 또한, 마우스 OVA 유발 기도 과민성 모델에 있어서, 항 MDC 항체는 폐 간질에 집적되는 호산구의 수를 줄여 기도 과민성을 억제하였다(J. Immunology, 163 , 403(1999)).
MCP-1과 그 수용체인 CCR2는 대식세포의 염증 부위로의 침윤에 관여하고 있다. 항 MCP-1 항체는 래트 항 Thy1.1 항체 신장염 모델에 있어서, 사구체로의 단구, 대식세포의 침윤에 대한 억제 효과를 보였다(Kidney Int., 51 , 770(1997)).
이와 같이, 케모카인 수용체는 각종 특이적인 세포에 있어서 어떤 특정한 시기에 발현되며, 그 효과기 세포가 케모카인이 생성되는 곳에 집적된다고 하는 메카니즘을 통하여 염증, 면역 반응의 제어에 크게 관여하고 있다.
인간 면역 부전 바이러스(이하, HIV라 약칭함) 감염에 의해 유발되는 후천성 면역 부전 증후군(에이즈(AIDS)라 약칭함)은 최근 들어 가장 그 치료법이 갈망되고 있는 질환의 하나이다. 주요한 표적 세포인 CD4 양성 세포에 HIV의 감염이 한번 성립하면, HIV는 환자의 체내에서 증식을 반복하고, 이윽고 면역 기능을 담당하는 T 세포를 괴멸적으로 파괴한다. 이 과정에서 서서히 면역 기능이 저하되어 발열, 설사, 림프절의 종창(腫脹) 등의 다양한 면역 부전 상태를 보이게 되고, 카리니 폐렴 등의 각종 기회 감염증을 병발하기 쉽게 한다. 이러한 상태가 에이즈의 발증이며, 카포시 육종 등의 악성 종양을 유발하여 중독화하는 것은 잘 알려져 있다.
현재 에이즈에 대한 각종 예방, 치료 방법으로서는, 예컨대, (1) 역전사 효소 억제제나 프로테아제 억제제의 투여에 따른 HIV의 증식 억제, (2) 면역 부활 작용이 있는 약물의 투여에 따른 기회 감염증의 예방, 완화 등이 시도되고 있다.
HIV는 면역계의 중추를 담당하는 헬퍼 T 세포에 주로 감염된다. 그 때, T 세포의 막 상에 발현하고 있는 막단백질 CD4를 이용하는 것은 1985년부터 알려져 있다(Cell, 52 , 631(1985)). CD4 분자는 433개의 아미노산 잔기로 이루어지고, 성숙 헬퍼 T 세포 이외에 대식세포, 일부의 B 세포, 혈관 내피 세포, 피부 조직의 랑겔 한스 세포, 림프 조직에 있는 수상 세포, 중추 신경계의 그리아 세포 등에서 발현되는 것을 볼 수 있다. 그러나, CD4 분자만으로는 HIV의 감염이 성립되지 않는 것이 밝혀짐에 따라 HIV가 세포에 감염될 때에 관계되는 CD4 분자 이외의 인자 존재의 가능성이 시사되게 되었다.
1996년에 와서 CD4 분자 이외의 HIV 감염에 관계되는 인자로서 Fusin이라는 세포막 단백질이 확인되었다(Science, 272 , 872(1996)). 이 Fusin 분자는 스트로마 세포 유래 인자-1(Stromal Derived Factor-1: SDF-1이라 약칭함)의 수용체(즉, CXCR4임)인 것이 증명되었다. 더욱이, 시험관내에서 SDF-1이 T 세포 지향성(X4) HIV의 감염을 특이적으로 억제하는 것도 증명되었다(Nature, 382 , 829(1996), Nature, 382 , 833(1996)). 즉, SDF-1이 HIV보다 먼저 CXCR4와 결합함으로써 HIV가세포에 감염되기 위한 거점을 없애어 HIV의 감염이 억제되었다고 생각된다.
또한, 동일 무렵, 다른 케모카인 수용체로서, RANTES, MIP-1α, MIP-1β의 수용체인 CCR5도 대식세포 지향성(R5) HIV가 감염될 때에 이용되는 것이 발견되엇다(Science, 272 , 1955(1996)).
따라서, HIV와 CXCR4 또는 CCR5를 서로 없앨 수 있는 것, 혹은 HIV 바이러스와 결합하고 그 바이러스가 CXCR4나 CCR5와 결합할 수 없는 상태로 하게 하는 것은 HIV 감염 억제제가 될 수 있는 것이다. 또한 당초, HIV 감염 억제제로서 발견된 저분자 화합물이 실은 CXCR4의 길항 물질인 것을 나타낸 예도 있다(Nature Medicine, 4 , 72(1998)).
이상으로부터, 케모카인/케모카인 수용체는 염증, 면역 질환 또는 HIV 감염에 깊게 관여하고 있다고 생각된다. 예컨대, 각종 염증성 질환, 천식, 아토피성 피부염, 두드러기, 알레르기 질환(알레르기성 기관지 폐 아스페르길루스증, 알레르기성 호산구성 위장증 등), 신장염, 신장증, 간염, 관절염, 만성관절 류머티스, 건선, 비염, 결막염, 허혈 재관류 상해의 억제, 다발성 경화증, 궤혈성 대장염, 급성 호흡 궁박 증후군, 세균 감염에 따른 쇼크, 당뇨병, 자기 면역 질환의 치료, 이식 장기 거부 반응, 면역 억제, 암전이 예방, 후천성 면역 부전 증후군에 관여하고 있다고 생각된다.
한편, WO97/11940호 명세서에는 하기 화학식 Z로 표시되는 화합물이 혈소판 응집 억제에 유용하다는 취지의 기재가 있다.
상기 식에서 AiZ및 BjZ는 각각 별개로 탄소, 질소, 산소 또는 유황에서 선택되고(단, AiZ의 적어도 1개의 원자는 탄소이며, 또한 적어도 1개의 BjZ는 탄소임);
Aiz및 BjZ에 의해 형성되는 스피로 이고리는 각각 경우에 따라 부분적으로 불포화이어도 좋으며,
pZ 및 qZ는 각각 별개로 2에서 6까지의 수이고,
mZ는 O에서 pZ까지의 수이며,
R10Z는 동일하거나 또는 다르고, 수소, 알킬, 할로 치환 알킬, 알케닐, 알키닐, 시클로알킬, =O, =S 등에서 각각 별개로 선택되는 비간섭성 치환기이며,
nZ은 0에서 qZ까지의 수이고,
R0Z는 동일하거나 또는 다르며, 수소, 알킬, 할로 치환 알킬, 알케닐, 알키닐, 시클로알킬, =0, =S 등에서 각각 별개로 선택되는 비간섭성 치환기이고,
-(LZ)-는 결합이거나 또는 탄소, 질소, 유황 및 산소에서 선택되는 1개에서 10개의 원자로 이루어진 2가의 치환 혹은 비치환쇄이며,
QZ는 1개 또는 2개 이상의 염기성 라디칼을 포함한 염기성기이고, 또한
R3Z는 1개 또는 2개 이상의 산성 라디칼을 포함한 산성기이다.
또한, WO98/25605호 명세서에는 화학식 Y로 표시되는 화합물이 케모카인 수용체 조절인자로서 유용하다는 취지의 기재가 있다.
상기 식에서 mY 또는 lY는 각각 독립적으로 0, 1, 2, 3, 4 또는 5를 나타내고,
R1Y는 수소 원자, C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기 등을 나타내며,
WY는 단일 결합, C1∼3 알킬기, 옥소 등으로 치환한 C1∼3 알킬기 등을 나타내고,
QY는 -NR2-, -O-, -S-, -S(O)- 또는 -SO2-를 나타내며,
XY는 단일 결합, C1∼3 알킬기, 옥소 등으로 치환한 C1∼3 알킬기 등을 나타내고,
YY-ZY고리는 페닐, 나프틸, 헤테로아릴을 나타낸다. 단, 각 기호의 정의는 일부를 발췌한 것이다.
본 발명은 트리아자스피로[5. 5]운데칸 유도체 및 이들을 유효성분으로서 함유하는 약제에 관한 것이다.
더욱 상세하게는, 하기 화학식 I로 표시되는 트리아자스피로[5. 5]운데칸 유도체, 이들의 4급 암모늄염, 이들의 N-옥사이드, 이들의 비독성염, 이들의 제조 방법 및 이들을 유효성분으로서 함유하는 약제에 관한 것이다.
상기 식에서 모든 기호는 후기와 동일한 의미를 나타낸다.
발명의 개시
본 발명의 발명자들은 각종 케모카인/케모카인 수용체의 작용을 제어하는 화합물을 발견하기 위해 예의 검토를 거듭한 결과, 화학식 I로 표시되는 트리아자스피로[5. 5]운데칸 유도체가 본 발명의 목적을 달성하는 것을 발견하여 본 발명을 완성하였다.
본 발명은,
i) 하기 화학식 I로 표시되는 트리아자스피로[5. 5]운데칸 유도체, 이들의 4급 암모늄염, 이들의 N-옥사이드 또는 이들의 비독성염,
ii) 화학식 I로 표시되는 화합물, 이들의 4급 암모늄염, 이들의 N-옥사이드, 또는 이들의 비독성염의 제조 방법,
iii) 화학식 I로 표시되는 화합물, 이들의 4급 암모늄염, 이들의 N-옥사이드, 또는 이들의 비독성염을 유효성분으로서 함유하는 약제에 관한 것이다.
화학식 I
상기 식에서 R1은
(1) 수소 원자,
(2) C1∼18 알킬기,
(3) C2∼18 알케닐기,
(4) C2∼18 알키닐기,
(5) -COR6,
(6) -CONR7R8,
(7) -COOR9,
(8) -SO2R10,
(9) -COCOOR11,
(10) -CONR12COR13,
(11) Cyc1, 또는
(12) 임의로 선택된 1∼5개의 (a) 할로겐 원자, (b) -CONR7R8, (c) -COOR9, (d) -OR14, (e) -SR15, (f) -NR16R17, (g) -NR18COR19, (h) -SO2NR20R21, (i) -OCOR22, (j) -NR23SO2R24, (k) -NR25COOR26, (l) -NR27CONR28R29, (m) Cyc1, (n) 케토기, (o) -N(SO2R24)2에 의해 치환된 C1∼18 알킬기, C2∼18 알케닐기, 또는 C2∼18 알키닐기를 나타내고,
(기 중, R6∼R9, R11∼R21, R23, R25및 R27∼R29는 각각 독립적으로
(1) 수소 원자,
(2) C1∼8 알킬기,
(3) C2∼8 알케닐기,
(4) C2∼8 알키닐기,
(5) Cyc1, 또는
(6) 임의로 선택된 1∼5개의 (a) Cyc1, (b) 할로겐 원자, (c) -OR30, (d) -SR31, (e) -NR32R33, (f) -COOR34, (g) -CONR35R36, (h) -NR37COR38, (i) -NR39SO2R40, (j) -N(SO2R40)2에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, 또는 C2∼8 알키닐기를 나타내거나,
R7과 R8, R20과 R21, R28과 R29는 함께 1) C2∼6 알킬렌기, 2) -(C2∼6 알킬렌기)-O-(C2∼6 알킬렌기)-, 3) -(C2∼6 알킬렌기)-S-(C2∼6 알킬렌기)-, 또는 4) -(C2∼6 알킬렌기)-NR195-(C2∼6 알킬렌기)-를 나타내고(기 중, R195는 수소 원자, C1∼8 알킬기, 페닐기, 또는 페닐기에 의해 치환된 C1∼8 알킬기를 나타냄),
R10, R22, R24및 R26은 각각 독립적으로
(1) C1∼8 알킬기,
(2) C2∼8 알케닐기,
(3) C2∼8 알키닐기,
(4) Cyc1, 또는
(5) 임의로 선택된 1∼5개의 (a) Cyc1, (b) 할로겐 원자, (c) -OR30, (d) -SR31, (e) -NR32R33, (f) -COOR34, (g) -CONR35R36, (h) -NR37COR38, (i) -NR39SO2R40, (j) -N(SO2R40)2에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, 또는 C2∼8 알키닐기를 나타내며,
(기 중, R30∼R37및 R39는 각각 독립적으로 수소 원자, C1∼8 알킬기, Cyc1, 또는 Cyc1에 의해 치환된 C1∼8 알킬기를 나타내거나,
R35와 R36은 함께 1) C2∼6 알킬렌기, 2) -(C2∼6 알킬렌기)-O-(C2∼6 알킬렌기)-, 3) -(C2∼6 알킬렌기)-S-(C2∼6 알킬렌기)-, 또는 4) -(C2∼6 알킬렌기)-NR196-(C2∼6 알킬렌기)-를 나타내고(기 중, R196은 수소 원자, C1∼8 알킬기, 페닐기, 또는 페닐기에 의해 치환된 C1∼8 알킬기를 나타냄),
R38및 R40은 각각 독립적으로 C1∼8 알킬기, Cyc1, 또는 Cyc1에 의해 치환된C1∼8 알킬기를 나타냄)
Cyc1은 C3∼15의 단고리, 이고리, 또는 삼고리식(축합 또는 스피로) 탄소고리, 또는 1∼4개의 질소 원자, 1∼3개의 산소 원자 및/또는 1∼3개의 유황 원자를 포함하는 3∼15원의 단고리, 이고리, 또는 삼고리식(축합 또는 스피로) 복소고리를 나타낸다.
단, Cyc1은 1∼5개의 R51에 의해 치환되어도 좋고,
R51은
(1) C1∼8 알킬기,
(2) C2∼8 알케닐기,
(3) C2∼8 알키닐기,
(4) 할로겐 원자,
(5) 니트로기,
(6) 트리플루오로메틸기
(7) 트리플루오로메톡시기,
(8) 니트릴기,
(9) 케토기,
(10) Cyc2
(11) -OR52,
(12) -SR53,
(13) -NR54R55,
(14) -COOR56,
(15) -CONR57R58,
(16) -NR59COR60,
(17) -SO2NR61R62,
(18) -OCOR63,
(19) -NR64SO2R65,
(20) -NR66COOR67,
(21) -NR68CONR69R70,
(22) -B(OR71)2,
(23) -SO2R72,
(24) -N(SO2R72)2, 또는
(25) 임의로 선택된 1∼5개의 (a) 할로겐 원자, (b) Cyc2, (c) -OR52, (d) -SR53, (e) -NR54R55, (f) -COOR56, (g) -CONR57R58, (h) -NR59COR60, (i) -SO2NR61R62, (j) -OCOR63, (k) -NR64SO2R65, (l) -NR66COOR67, (m) -NR68CONR69R70, (n) -B(OR71)2, (o) -SO2R72, (p) -N(SO2R72)2에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기를 나타냄)
(기 중, R52∼R62, R64, R66및 R68∼R71은 각각 독립적으로
1) 수소 원자, 2) C1∼8 알킬기, 3) C2∼8 알케닐기, 4) C2∼8 알키닐기, 5) Cyc2, 또는 6) Cyc2, -OR73, -COOR74, -NR75R76에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기를 나타내거나,
R57과 R58, R61과 R62, R69와 R70은 함께 1) C2∼6 알킬렌기, 2) -(C2∼6 알킬렌기)-O-(C2∼6 알킬렌기)-, 3) -(C2∼6 알킬렌기)-S-(C2∼6 알킬렌기)-, 또는 4) -(C2∼6 알킬렌기)-NR197-(C2∼6 알킬렌기)-를 나타내고(기 중, R197은 수소 원자, C1∼8 알킬기, 페닐기, 또는 페닐기에 의해 치환된 C1∼8 알킬기를 나타냄),
R63, R65, R67및 R72는 각각 독립적으로 1) C1∼8 알킬기, 2) C2∼8 알케닐기, 3) C2∼8 알키닐기, 4) Cyc2, 또는 5) Cyc2, -OR73, -COOR74, -NR75R76에 의해 치환된C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기를 나타내며,
(기 중, R73∼R76은 각각 독립적으로 수소 원자, C1∼8 알킬기, Cyc2, 또는 Cyc2에 의해 치환된 C1∼8 알킬기를 나타냄)
Cyc2는 Cyc1과 동일한 의미를 나타낸다.
단, Cyc2는 1∼5개의 R77에 의해 치환되어도 좋고,
R77은
1) C1∼8 알킬기,
2) 할로겐 원자,
3) 니트로기,
4) 트리플루오로메틸기,
5) 트리플루오로메톡시기,
6) 니트릴기,
7) -OR78,
8) -NR79R80,
9) -COOR81,
10) -SR82,
11) -CONR83R84,
12) C2∼8 알케닐기,
13) C2∼8 알키닐기,
14) 케토기,
15) Cyc6,
16) -NR161COR162,
17) -SO2NR163R164,
18) -OCOR165,
19) -NR166SO2R167,
20) -NR168COOR169,
21) -NR170CONR171R172,
22) -SO2R173,
23) -N(SO2R167)2,
24) 임의로 선택된 1∼5개의 (a) 할로겐 원자, (b) -OR78, (c) -NR79R80, (d) -COOR81, (e) -SR82, (f) -CONR83R84, (g) 케토기, (h) Cyc6, (i) -NR161COR162, (j) -SO2NR163R164, (k) -OCOR165, (l) -NR166SO2R167, (m) -NR168COOR169, (n) -NR170CONR171R172, (o) -SO2R173, (p) -N(SO2R167)2에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기를 나타냄)
(기 중, R78∼R84, R161∼R164, R166, R168및 R170∼R172는 각각 독립적으로 (a) 수소 원자, (b) C1∼8 알킬기, (c) C2∼8 알케닐기, (d) C2∼8 알키닐기, (e) Cyc6, (f) Cyc6, -OR174, -COOR175, -NR176R177, -CONR178R179에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기를 나타내거나,
R83과 R84, R163과 R164, R171과 R172는 함께 1) C2∼6 알킬렌기, 2) -(C2∼6 알킬렌기)-O-(C2∼6 알킬렌기)-, 3) -(C2∼6 알킬렌기)-S-(C2∼6 알킬렌기)-, 또는 4) -(C2∼6 알킬렌기)-NR198-(C2∼6 알킬렌기)-를 나타내고(기 중, R198은 수소 원자, C1∼8 알킬기, 페닐기, 또는 페닐기에 의해 치환된 C1∼8 알킬기를 나타냄),
R165, R167, R169및 R173은 각각 독립적으로 (a) C1∼8 알킬기, (b) C2∼8 알케닐기, (c) C2∼8 알키닐기, (d) Cyc6, 또는 (e) Cyc6, -OR174, -COOR175, -NR176R177, -CONR178R179에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기를 나타냄)
(기 중, R174∼R177은 각각 독립적으로 1) 수소 원자, 2) C1∼8 알킬기, 3)Cyc6, 또는 4) Cyc6에 의해 치환된 C1∼8 알킬기를 나타내거나,
R178과 R179는 함께 1) C2∼6 알킬렌기, 2) -(C2∼6 알킬렌기)-O-(C2∼6 알킬렌기)-, 3) -(C2∼6 알킬렌기)-S-(C2∼6 알킬렌기)-, 또는 4) -(C2∼6 알킬렌기)-NR199-(C2∼6 알킬렌기)-를 나타내고(기 중, R199는 수소 원자, C1∼8 알킬기, 페닐기, 또는 페닐기에 의해 치환된 C1∼8 알킬기를 나타냄),
Cyc6은 C3∼8의 단고리식 탄소고리 또는 1∼4개의 질소 원자, 1∼2개의 산소 원자 및/또는 1∼2개의 유황 원자를 포함하는 3∼8원의 단고리식 복소고리를 나타낸다.
단, Cyc6은 1∼5개의 R180에 의해 치환되어도 좋고,
R180은
(1) C1∼8 알킬기,
(2) 할로겐 원자,
(3) 니트로기,
(4) 트리플루오로메틸기,
(5) 트리플루오로메톡시기,
(6) 니트릴기,
(7) -OR181,
(8) -NR182R183,
(9) -COOR184,
(10) -SR185, 또는
(11) -CONR186R187을 나타내고
(기 중, R181∼R187은 각각 독립적으로 1) 수소 원자, 2) C1∼8 알킬기, 3) 페닐기, 또는 4) 페닐기에 의해 치환된 C1∼8 알킬기를 나타내거나,
R182와 R183, R186과 R187은 함께 1) C2∼6 알킬렌기, 2) -(C2∼6 알킬렌기)-O-(C2∼6 알킬렌기)-, 3) -(C2∼6 알킬렌기)-S-(C2∼6 알킬렌기)-, 또는 4) - (C2∼6 알킬렌기)-NR200-(C2∼6 알킬렌기)-를 나타냄(기 중, R200은 수소 원자, C1∼8 알킬기, 페닐기, 페닐기에 의해 치환된 C1∼8 알킬기를 나타냄)),
R2는
(1) 수소 원자,
(2) C1∼8 알킬기,
(3) C2∼8 알케닐기,
(4) C2∼8 알키닐기,
(5) -OR90,
(6) Cyc3, 또는
(7) 임의로 선택된 1∼5개의 (a) 할로겐 원자, (b) -OR90, (c) -SR91, (d) -NR92R93, (e) -COOR94, (f) -CONR95R96, (g) -NR97COR98, (h) -SO2NR99R100, (i) -OCOR101, (j) -NR102SO2R103, (k) -NR104COOR105, (l) -NR106CONR107R108, (m) Cyc3, (n) 케토기, (o) -N(SO2R103)2에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기 또는 C2∼8 알키닐기를 나타내고,
(기 중, R90∼R100, R102, R104및 R106∼R108은 각각 독립적으로 1) 수소 원자, 2) C1∼8 알킬기, 3) C2∼8 알케닐기, 4) C2∼8 알키닐기, 5) Cyc3, 또는 6) Cyc3에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기를 나타내거나,
R95와 R96, R99와 R100, R107과 R108은 함께 1) C2∼6 알킬렌기, 2) -(C2∼6 알킬렌기)-O-(C2∼6 알킬렌기)-, 3) -(C2∼6 알킬렌기)-S-(C2∼6 알킬렌기)-, 또는 4) -(C2∼6 알킬렌기)-NR201-(C2∼6 알킬렌기)-를 나타내고(기 중, R201은 수소 원자, C1∼8 알킬기, 페닐기, 또는 페닐기에 의해 치환된 C1∼8 알킬기를 나타냄),
R101, R103및 R105는 각각 독립적으로 1) C1∼8 알킬기, 2) C2∼8 알케닐기, 3) C2∼8 알키닐기, 또는 4) Cyc3 또는 Cyc3에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기를 나타내며,
Cyc3은 Cyc1과 동일한 의미를 나타낸다.
단, Cyc3은 1∼5개의 R109에 의해 치환되어도 좋고,
R109는 R51과 동일한 의미를 나타냄)
R3및 R4는 각각 독립적으로
(1) 수소 원자,
(2) C1∼8 알킬기,
(3) C2∼8 알케닐기,
(4) C2∼8 알키닐기,
(5) -COOR120,
(6) -CONR121R122,
(7) Cyc4, 또는
(8) 임의로 선택된 1∼5개의 (a) 할로겐 원자, (b) 니트릴기, (c) Cyc4, (d) -COOR120, (e) -CONR121R122, (f) -OR123, (g) -SR124, (h) -NR125R126, (i) -NR127COR128, (j) -SO2NR129R130, (k) -OCOR131, (l) -NR132SO2R133, (m) -NR134COOR135, (n) -NR136CONR137R138, (o) -S-SR139, (p) -NHC(=NH)NHR140, (q) 케토기, (r) -NR145CONR146COR147, (s) -N(SO2R133)2에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, 또는 C2∼8 알키닐기를 나타내고,
(기 중, R120∼R130, R132, R134, R136∼R138, R145및 R146은 각각 독립적으로 1) 수소 원자, 2) C1∼8 알킬기, 3) C2∼8 알케닐기, 4) C2∼8 알키닐기, 5) Cyc4, 또는 6) Cyc4, 할로겐 원자, -OR148, -SR149, -COOR150, 또는 -NHCOR141에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기를 나타내거나,
R121과 R122, R129와 R130, R137과 R138은 함께 1) C2∼6 알킬렌기, 2) -(C2∼6 알킬렌기)-O-(C2∼6 알킬렌기)-, 3) -(C2∼6 알킬렌기)-S-(C2∼6 알킬렌기)-, 또는 4) -(C2∼6 알킬렌기)-NR202-(C2∼6 알킬렌기)-를 나타내고(기 중, R202는 수소 원자, C1∼8 알킬기, 페닐기, 페닐기에 의해 치환된 C1∼8 알킬기를 나타냄),
R131, R133, R135, R139및 R147은 각각 독립적으로 1) C1∼8 알킬기, 2) C2∼8 알케닐기, 3) C2∼8 알키닐기, 4) Cyc4, 또는 5) Cyc4, 할로겐 원자, -OR148, -SR149, -COOR150, 또는 -NHCOR141에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기를 나타내고,
R140은 수소 원자, -COOR142, 또는 -SO2R143을 나타내고,
(기 중, R141∼R143은 각각 독립적으로 1) C1∼8 알킬기, 2) C2∼8 알케닐기, 3) C2∼8 알키닐기, 4) Cyc4, 또는 5) Cyc4에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기를 나타내며,
R148∼R150은 각각 독립적으로 1) 수소 원자, 2) C1∼8 알킬기, 3) C2∼8 알케닐기, 4) C2∼8 알키닐기, 5) Cyc4, 또는 6) Cyc4에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기를 나타내고,
Cyc4는 Cyc1과 동일한 의미를 나타낸다.
단, Cyc4는 1∼5개의 R144에 의해 치환되어도 좋고, R144는 R51과 동일한 의미를 나타냄)를 나타내거나
R3과 R4는 함께
(기 중, R190및 R191은 각각 독립적으로 R3또는 R4와 동일한 의미를 나타냄)를 나타내고,
R5는
(1) 수소 원자,
(2) C1∼8 알킬기,
(3) Cyc5, 또는
(4) Cyc5에 의해 치환된 C1∼8 알킬기를 나타낸다.
(기 중, Cyc5는 Cyc1과 동일한 의미를 나타낸다.
단, Cyc5는 1∼5개의 R160에 의해 치환되어도 좋고, R160은 R51과 동일한 의미를 나타낸다.
본 발명에 있어서, C1∼18 알킬기란, 메틸, 에틸, 프로필, 부틸, 펜틸, 헥실, 헵틸, 옥틸, 노닐, 데실, 운데실, 도데실, 트리데실, 테트라데실, 펜타데실, 헥사데실, 헵타데실, 옥타데실기 및 이들의 이성체를 나타낸다.
C2∼18 알케닐기란, 이중 결합을 1∼9개(바람직하게는 1∼4개) 가져도 좋은 C2∼18 알킬렌기를 의미한다. 예컨대, 비닐, 프로페닐, 부테닐, 펜테닐, 헥세닐, 헵테닐, 옥테닐, 노네닐, 데세닐, 운데세닐, 도데세닐, 트리데세닐, 테트라데세닐, 펜타데세닐, 헥사데세닐, 헵타데세닐, 옥타데세닐, 부타디에닐, 펜타디에닐, 헥사디에닐, 헵타디에닐, 옥타디에닐, 노나디에닐, 데카디에닐, 운데카디에닐, 도데카디에닐, 트리데카디에닐, 테트라데카디에닐, 펜타데카디에닐, 헥사데카디에닐, 헵타데카디에닐, 옥타데카디에닐, 헥사트리에닐, 헵타트리에닐, 옥타트리에닐, 노나트리에닐, 데카트리에닐, 운데카트리에닐, 도데카트리에닐, 트리데카트리에닐, 테트라데카트리에닐, 펜타데카트리에닐, 헥사데카트리에닐, 헵타데카트리에닐, 옥타데카트리에닐기 및 이들의 이성체기 등을 들 수 있다.
C2∼18 알키닐기란, 삼중 결합을 1∼9개(바람직하게는 1∼4개) 가져도 좋은 C2∼18 알킬렌기를 의미한다. 예컨대, 에티닐, 프로피닐, 부티닐, 펜티닐, 헥시닐, 헵티닐, 옥티닐, 노니닐, 데시닐, 운데시닐, 도데시닐, 트리데시닐, 테트라데시닐, 펜타데시닐, 헥사데시닐, 헵타데시닐, 옥타데시닐, 부타디이닐, 펜타디이닐, 헥사디이닐, 헵타디이닐, 옥타디이닐, 노나디이닐, 데카디이닐, 운데카디이닐, 도데카디이닐, 트리데카디이닐, 테트라데카디이닐, 펜타데카디이닐, 헥사데카디이닐, 헵타데카디이닐, 옥타데카디이닐, 헥사트리이닐, 헵타트리이닐, 옥타트리이닐, 노나트리이닐, 데카트리이닐, 운데카트리이닐, 도데카트리이닐, 트리데카트리이닐, 테트라데카트리이닐, 펜타데카트리이닐, 헥사데카트리이닐, 헵타데카트리이닐, 옥타데카트리이닐기 및 이들의 이성체기 등을 들 수 있다.
할로겐 원자란, 염소, 브롬, 불소, 요오드 원자를 들 수 있다.
C1∼8 알킬기란, 메틸, 에틸, 프로필, 부틸, 펜틸, 헥실, 헵틸, 옥틸기 및 이들의 이성체를 나타낸다.
C2∼8 알케닐기란, 이중 결합을 1∼4개 가져도 좋은 C2∼8 알킬렌기를 의미한다. 예컨대, 비닐, 프로페닐, 부테닐, 펜테닐, 헥세닐, 헵테닐, 옥테닐, 부타디에닐, 펜타디에닐, 헥사디에닐, 헵타디에닐, 옥타디에닐, 헥사트리에닐, 헵타트리에닐, 옥타트리에닐기 및 이들의 이성체기 등을 들 수 있다.
C2∼8 알키닐기란, 삼중 결합을 1∼4개 가져도 좋은 C2∼8 알킬렌기를 의미한다. 예컨대, 에티닐, 프로피닐, 부티닐, 펜티닐, 헥시닐, 헵티닐, 옥티닐, 부타디이닐, 펜타디이닐, 헥사디이닐, 헵타디이닐, 옥타디이닐, 헥사트리이닐, 헵타트리이닐, 옥타트리이닐기 및 이들의 이성체기 등을 들 수 있다.
C2∼6 알킬렌기란, 메틸렌, 에틸렌, 트리메틸렌, 테트라메틸렌, 펜타메틸렌, 헥사메틸렌기 및 이들의 이성체기 등을 들 수 있다.
C3∼15의 단고리, 이고리, 또는 삼고리식(축합 또는 스피로) 탄소고리란, 예컨대, 시클로프로판, 시클로부탄, 시클로펜탄, 시클로헥산, 시클로헵탄, 시클로옥탄, 시클로펜텐, 시클로헥센, 시클로헵텐, 시클로옥텐, 시클로펜타디엔, 시클로헥사디엔, 시클로헵타디엔, 시클로옥타디엔, 벤젠, 인덴, 나프탈렌, 인단, 테트라히드로나프탈렌, 비시클로[3. 3. 0]옥탄, 비시클로[4. 3. 0]노난, 비시클로[4. 4. 0]데칸, 스피로[4. 4]노난, 스피로[4. 5]데칸, 스피로[5. 5]운데칸, 비시클로[3. 1. 1]헵탄, 비시클로[3. 3. 1]-2-헵텐, 플루오렌, 안트라센 등을 들 수 있다.
1∼4개의 질소 원자, 1∼3개의 산소 원자 및/또는 1∼3개의 유황 원자를 포함하는 3∼15원의 단고리, 이고리, 또는 삼고리식(축합 또는 스피로) 복소고리란, 예컨대, 1∼4개의 질소 원자, 1∼3개의 산소 원자 및/또는 1∼3개의 유황 원자를 포함하는 3∼15원의 단고리, 이고리, 또는 삼고리식(축합 또는 스피로) 복소고리 아릴, 또는 그 일부 또는 전부가 포화한 것이다.
1∼4개의 질소 원자, 1∼3개의 산소 원자 및/또는 1∼3개의 유황 원자를 포함하는 3∼15원의 단고리, 이고리, 또는 삼고리식(축합 또는 스피로) 복소고리아릴로서는, 피롤, 이미다졸, 트리아졸, 테트라졸, 피라졸, 피리딘, 피라진, 피리미딘, 피리다진, 아제핀, 디아제핀, 푸란, 피란, 옥세핀, 티오펜, 티아인(티오피란), 티에핀, 옥사졸, 이소옥사졸, 티아졸, 이소티아졸, 프라잔, 옥사디아졸, 옥사진, 옥사디아진, 옥사제핀, 옥사디아제핀, 티아디아졸, 티아진, 티아디아진, 티아제핀, 티아디아제핀, 인돌, 이소인돌, 벤조푸란, 이소벤조푸란, 벤조티오펜, 이소벤조티오펜, 인다졸, 퀴놀린, 이소퀴놀린, 프탈라진, 나프틸리딘, 퀴녹살린, 퀴나졸린, 신놀린, 벤조옥사졸, 벤조티아졸, 벤조이미다졸, 벤조옥세핀, 벤조옥사아제핀, 벤조옥사디아제핀, 벤조티에핀, 벤조티아아제핀, 벤조티아디아제핀, 벤조아제핀, 벤조디아제핀, 벤조프라잔, 벤조티아디아졸, 벤조트리아졸, 카르바졸, 아크리딘, 디벤조푸란, 디벤조티오펜고리 등을 들 수 있다.
상기한 1∼4개의 질소 원자, 1∼3개의 산소 원자 및/또는 1∼3개의 유황 원자를 포함하는 3∼15원의 단고리, 이고리, 또는 삼고리식(축합 또는 스피로) 복소고리이며, 일부 또는 전부 포화한 것으로서는,
피롤린, 피롤리딘, 이미다졸린, 이미다졸리딘, 피라졸린, 피라졸리딘, 트리아졸린, 트리아졸리딘, 테트라졸린, 테드라졸리딘, 디히드로피리딘, 테트라히드로피리딘, 피페리딘, 디히드로피라진, 테트라히드로피라진, 피페라진, 디히드로피리미딘, 테트라히드로피리미딘, 퍼히드로피리미딘, 디히드로피리다진, 테트라히드로피리다진, 퍼히드로피리다진, 디히드로아제핀, 테트라히드로아제핀, 퍼히드로아제핀, 디히드로디아제핀, 테트라히드로디아제핀, 퍼히드로디아제핀, 디히드로푸란, 테트라히드로푸란, 디히드로피란, 테트라히드로피란, 디히드로티오펜, 테트라히드로티오펜, 디히드로티아인(디히드로티오피란), 테트라히드로티아인(테트라히드로티오피란), 디히드로옥사졸, 테트라히드로옥사졸, 디히드로이소옥사졸, 테트라히드로이소옥사졸, 디히드로티아졸, 테트라히드로티아졸, 디히드로이소티아졸, 테트라히드로이소티아졸, 디히드로옥사디아졸, 테트라히드로옥사디아졸, 디히드로티오디아졸, 테트라히드로티오디아졸, 테트라히드로옥사디아진, 테트라히드로티아디아진, 테트라히드로옥사아제핀, 테트라히드로옥사디아제핀, 퍼히드로옥사아제핀, 퍼히드로옥사디아제핀, 테트라히드로티아아제핀, 테트라히드로티아디아제핀, 퍼히드로티아아제핀, 퍼히드로티아디아제핀, 모르폴린, 티오모르폴린, 인돌린, 이소인돌린, 디히드로벤조푸란, 퍼히드로벤조푸란, 디히드로이소벤조푸란, 퍼히드로이소벤조푸란, 디히드로벤조티오펜, 퍼히드로벤조티오펜, 디히드로이소벤조티오펜, 퍼히드로이소벤조티오펜, 디히드로인다졸, 퍼히드로인다졸, 디히드로퀴놀린, 테트라히드로퀴놀린, 퍼히드로퀴놀린, 디히드로이소퀴놀린, 테트라히드로이소퀴놀린, 퍼히드로이소퀴놀린, 디히드로프탈라진, 테트라히드로프탈라진, 퍼히드로프탈라진, 디히드로나프틸리딘, 테트라히드로나프틸리딘, 퍼히드로나프틸리딘, 디히드로퀴녹살린, 테트라히드로퀴녹살린, 퍼히드로퀴녹살린, 디히드로퀴나졸린, 테트라히드로퀴나졸린, 퍼히드로퀴나졸린, 디히드로신놀린, 테트라히드로신놀린, 퍼히드로신놀린, 디히드로벤조옥사졸, 퍼히드로벤조옥사졸, 디히드로벤조티아졸, 퍼히드로벤조티아졸, 디히드로벤조이미다졸, 퍼히드로벤조이미다졸, 디히드로카르바졸, 테트라히드로카르바졸, 퍼히드로카르바졸, 디히드로아크리딘, 테트라히드로아크리딘, 퍼히드로아크리딘, 디히드로디벤조푸란, 디히드로디벤조티오펜, 테트라히드로디벤조푸란, 테트라히드로디벤조티오펜, 퍼히드로디벤조푸란, 퍼히드로디벤조티오펜, 디옥솔란, 디옥산, 디티올란, 디티안, 벤조디옥살란, 벤조디옥산, 벤조디티올란, 벤조디티안, 2,4,6-트리옥사스피로[비시클로[3. 3. 0]옥탄-3,1'-시클로헥산], 1,3-디옥솔라노[4, 5-g]크로멘, 2-옥사비시클로[2. 2. 1]헵탄고리 등을 들 수 있다.
C3∼8의 단고리식 탄소고리란, 예컨대, 시클로프로판, 시클로부탄, 시클로펜탄, 시클로헥산, 시클로헵탄, 시클로옥탄, 시클로펜텐, 시클로헥센, 시클로헵텐,시클로옥텐, 시클로펜타디엔, 시클로헥사디엔, 시클로헵타디엔, 시클로옥타디엔, 벤젠 등을 들 수 있다.
1∼4개의 질소 원자, 1∼2개의 산소 원자 및/또는 1∼2개의 유황 원자를 포함하는 3∼8원의 단고리식 복소고리란, 예컨대, 1∼4개의 질소 원자, 1∼2개의 산소 원자 및/또는 1∼2개의 유황 원자를 포함하는 3∼8원의 단고리식 복소고리아릴, 또는 그 일부 또는 전부가 포화한 것이다.
1∼4개의 질소 원자, 1∼2개의 산소 원자 및/또는 1∼2개의 유황 원자를 포함하는 3∼8원의 단고리식 복소고리아릴로서는, 피롤, 이미다졸, 트리아졸, 테트라졸, 피라졸, 피리딘, 피라진, 피리미딘, 피리다진, 아제핀, 디아제핀, 푸란, 피란, 옥세핀, 티오펜, 티아인(티오피란), 티에핀, 옥사졸, 이소옥사졸, 티아졸, 이소티아졸, 프라잔, 옥사디아졸, 옥사진, 옥사디아진, 옥사제핀, 옥사디아제핀, 티아디아졸, 티아진, 티아디아진, 티아제핀, 티아디아제핀고리 등을 들 수 있다.
상기한 1∼4개의 질소 원자, 1∼2개의 산소 원자 및/또는 1∼2개의 유황 원자를 포함하는 3∼8원의 단고리식 복소고리이며
일부 또는 전부 포화한 것으로서는 피롤린, 피롤리딘, 이미다졸린, 이미다졸리딘, 피라졸린, 피라졸리딘, 트리아졸린, 트리아졸리딘, 테트라졸린, 테트라졸리딘, 디히드로피리딘, 테트라히드로피리딘, 피페리딘, 디히드로피라진, 테트라히드로피라진, 피페라진, 디히드로피리미딘, 테트라히드로피리미딘, 퍼히드로피리미딘, 디히드로피리다진, 테트라히드로피리다진, 퍼히드로피리다진, 디히드로아제핀, 테트라히드로아제핀, 퍼히드로아제핀, 디히드로디아제핀, 테트라히드로디아제핀, 퍼히드로디아제핀, 디히드로푸란, 테트라히드로푸란, 디히드로피란, 테트라히드로피란, 디히드로티오펜, 테트라히드로티오펜, 디히드로티아인(디히드로티오피란), 테트라히드로티아인(테트라히드로티오피란), 디히드로옥사졸, 테트라히드로옥사졸, 디히드로이소옥사졸, 테트라히드로이소옥사졸, 디히드로티아졸, 테트라히드로티아졸, 디히드로이소티아졸, 테트라히드로이소티아졸, 디히드로옥사디아졸, 테트라히드로옥사디아졸, 디히드로티오디아졸, 테트라히드로티오디아졸, 테트라히드로옥사디아진, 테트라히드로티아디아진, 테트라히드로옥사아제핀, 테트라히드로옥사디아제핀, 퍼히드로옥사아제핀, 퍼히드로옥사디아제핀, 테트라히드로티아아제핀, 테트라히드로티아디아제핀, 퍼히드로티아아제핀, 퍼히드로티아디아제핀, 모르폴린, 티오모르폴린, 디옥솔란, 디옥산, 디티올란, 디티안 등을 들 수 있다.
본 발명에 있어서, R1기, R2기, R3기, R4기, R5기가 나타내는 각각의 기는 모두 바람직하다.
R1기로서는, Cyc1에 의해 치환된 C1∼18 알킬기, Cyc1에 의해 치환된 C2∼18 알케닐기, 또는 Cyc1에 의해 치환된 C2∼18 알키닐기가 바람직하고, 보다 바람직하게는 Cyc1에 의해 치환된 C1∼6 알킬기이다.
Cyc1로서는, C3∼10의 단고리 또는 이고리식(축합 또는 스피로) 탄소고리 또는 1∼4개의 질소 원자, 1∼2개의 산소 원자 및/또는 1∼2개의 유황 원자를 포함하는 3∼10원의 단고리 또는 이고리식(축합 또는 스피로) 복소고리가 바람직하고, 보다 바람직하게는, C5∼7의 단고리식 탄소고리아릴 또는 1∼4개의 질소 원자, 2개의산소 원자 및/또는 1개의 유황 원자를 포함하는 5∼10원의 단고리식 또는 이고리식 복소고리이다.
구체적으로 Cyc1로서는, 벤젠고리, 피라졸고리, 이미다졸고리, 푸란고리, 티오펜고리, 벤조디옥산고리, 티아졸고리, 퀴놀린고리가 바람직하다.
Cyc1의 치환기인 R51로서는, Cyc2, -OR52, -SR53, -NR54R55가 바람직하다. R52, R53, R54, R55로서는, C1∼8 알킬기, Cyc2가 바람직하고, 보다 바람직하게는, 메틸, 에틸, 프로필, 페닐기이다.
Cyc2로서는, C5∼7의 단고리식 탄소고리아릴 또는 1∼4개의 질소 원자, 1개의 산소 원자 및/또는 1개의 유황 원자를 포함하는 5∼7원의 단고리식 복소고리아릴이 바람직하고, 보다 바람직하게는, 벤젠고리이다.
Cyc2의 치환기인 R77로서는, -CONR83R84, -NR161COR162, -SO2NR163R164, -NR166SO2R167, -CONR83R84에 의해 치환된 C1∼8 알킬기, -NR161COR162에 의해 치환된 C1∼8 알킬기, -SO2NR163R164에 의해 치환된 C1∼8 알킬기, -NR166SO2R167에 의해 치환된 C1∼8 알킬기가 바람직하다. R83, R84, R161, R162, R163, R164, R166및 R167로서는, C1∼8 알킬기, Cyc6, -NR176R177에 의해 치환된 C1∼8 알킬기가 바람직하고, 보다 바람직하게는, 메틸, 에틸, 프로필, 페닐기, 디메틸아미노에틸기 등이다.
가장 바람직한 R1로서는, 페닐에틸기, 페닐프로필기, 페닐부틸기, 페닐펜틸기, 페닐헥실기, 4-메톡시페닐메틸기, 4-프로필옥시페닐메틸기, 4-페닐옥시페닐메틸기, 3,5-디메틸-1-페닐피라졸-4-일메틸기, 2-페닐이미다졸-4-일메틸기, 5-에틸푸란-2-일메틸기, 5-에틸티오펜-2-일메틸기, 3-클로로-5-메틸-1-페닐피라졸-4-일메틸기, 1,4-벤조디옥산-6일메틸기, 4-(4-메틸설포닐아미노페닐옥시)페닐메틸기, 4-(4-(2-디메틸아미노에틸설포닐아미노)페닐옥시)페닐메틸기, 4-(4-디메틸아미노설포닐페닐옥시)페닐메틸기, 4-(4-메틸카르보닐아미노페닐옥시)페닐메틸기, 4-(4-(2-디메틸아미노에틸카르보닐아미노)페닐옥시)페닐메틸기, 4-(4-디메틸아미노카르보닐페닐옥시)페닐메틸기 등을 들 수 있다.
R2로서는, C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기, Cyc3에 의해 치환된 C1∼8 알킬기가 바람직하다. 보다 바람직하게는, C1∼4 알킬기, C2∼4 알케닐기, C2∼4 알키닐기이다.
가장 바람직한 R2로서는, 에틸기, 프로필기, 부틸기, 2-프로페닐기, 2-부테닐기, 2-프로피닐기, 페닐메틸기, 티오펜-2-일메틸기, 2-부티닐기 등을 들 수 있다.
R3또는 R4로서는, 수소 원자, C1∼8 알킬기, Cyc4에 의해 치환된 C1∼8 알킬기, -OR123에 의해 치환된 C1∼8 알킬기, Cyc4와 -OR123에 의해 치환된 C1∼8 알킬기,-NR127COR128에 의해 치환된 C1∼8 알킬기, -NR132SO2R133에 의해 치환된 C1∼8 알킬기, -NR134COOR135에 의해 치환된 C1∼8 알킬기, -NR136CONR137R138에 의해 치환된 C1∼8 알킬기가 바람직하다. 보다 바람직하게는, C1∼4 알킬기, Cyc4에 의해 치환된 C1∼4알킬기, -OR123에 의해 치환된 C1∼4 알킬기, Cyc4와 -OR123에 의해 치환된 C1∼4 알킬기, -NR127COR128에 의해 치환된 C1∼4 알킬기, -NR132SO2R133에 의해 치환된 C1∼4 알킬기, -NR134COOR135에 의해 치환된 C1∼4 알킬기, -NR136CONR137R138에 의해 치환된 C1∼4 알킬기이다.
Cyc4로서는, 벤젠고리, 시클로헥산고리가 바람직하다.
R123으로서는, 수소 원자, C1∼4 알킬기, Cyc4, 또는 Cyc4에 의해 치환된 C1∼4 알킬기가 바람직하고, 보다 바람직하게는, 수소 원자, 메틸기, 에틸기, 페닐기, 페닐메틸기이다.
R127, R132, R134, R136및 R138로서는, 수소 원자 또는 메틸기가 바람직하다.
R128, R133, R135, R137로서는, Cyc4 또는 Cyc4에 의해 치환된 C1∼4 알킬기가 바람직하고, 보다 바람직하게는, 페닐기, 페닐메틸기, 페닐에틸기이다.
Cyc4의 치환기인 R144로서는, C1∼4 알킬기, 할로겐 원자, 페닐기, 페닐옥시기가 바람직하고, 보다 바람직하게는, 메틸기, 불소 원자, 염소 원자, 페닐기, 페닐옥시기이다.
가장 바람직한 R3또는 R4로서는 프로필기, 1-메틸프로필기, 2-메틸프로필기, 시클로헥실메틸기, 1-히드록시-2-메틸프로필기, 1-히드록시-1-시클로헥실메틸기, 3-(시클로펜틸에틸카르보닐)아미노부틸기, 3-(벤질옥시카르보닐)아미노프로필기, 3-(페닐카르보닐)아미노부틸기, 3-(페닐메틸카르보닐)아미노부틸기, 3-(페닐에틸카르보닐)아미노부틸기, 3-(페닐에테닐카르보닐)아미노부틸기, 3-(4-페닐페닐카르보닐)아미노부틸기, 3-(4-페닐옥시페닐아미노카르보닐)아미노부틸기, 3-(4-클로로페닐아미노카르보닐)아미노부틸기, 3-(4-플루오로페닐아미노카르보닐)아미노부틸기, 3-(페닐메틸아미노카르보닐)아미노부틸기, 3-(4-트리플루오로메틸설포닐)아미노부틸기, 4-(시클로펜틸에틸카르보닐)아미노부틸기, 4-(벤질옥시카르보닐)아미노부틸기, 4-(페닐카르보닐)아미노부틸기, 4-(페닐메틸카르보닐)아미노부틸기, 4-(페닐에틸카르보닐)아미노부틸기, 4-(페닐에테닐카르보닐)아미노부틸기, 4-(4-페닐페닐카르보닐)아미노부틸기, 4-(4-페닐옥시페닐아미노카르보닐)아미노부틸기, 4-(4-클로로페닐아미노카르보닐)아미노부틸기, 4-(4-플루오로페닐아미노카르보닐)아미노부틸기, 4-(페닐메틸아미노카르보닐)아미노부틸기, 4-(4-트리플루오로메틸설포닐)아미노부틸기를 들 수 있다.
R5로서는, 수소 원자 또는 메틸기가 바람직하다.
화학식 I로 표시되는 본 발명 화합물 중, 바람직한 화합물로서는, 하기 화학식 Ia로 표시되는 화합물을 들 수 있다.
상기 식에서 R2는 C1∼8 알킬기를 나타내고,
R3은 C1∼8 알킬기 또는 C3∼7 시클로알킬(C1∼4)알킬기를 나타내며,
R5는 수소 원자 또는 C1∼8 알킬기를 나타내고,
A는 단일 결합 또는 C1∼10 알킬렌기를 나타내며,
D 고리는 C3∼10의 단고리 또는 이고리식(축합 또는 스피로) 탄소고리 또는 3∼10원의 단고리 또는 이고리식(축합 또는 스피로) 복소고리를 나타내고,
m은 0 또는 1∼4의 정수를 나타내며,
R300은 C1∼4 알킬기, C1∼4 알콕시기, 페닐기, 페녹시기, 또는 벤질옥시기를 나타낸다.
D 고리가 나타내는 C3∼10의 탄소고리로서는, C3∼10의 단고리식 또는 이고리식 탄소고리가 바람직하고, 보다 바람직하게는, C3∼7의 단고리식 탄소고리, 또는 C8∼10의 이고리식 탄소고리이다.
또한, D 고리가 나타내는 3∼10원의 복소고리로서는, 1∼4개의 질소 원자, 1∼2개의 산소 원자 및/또는 1개의 유황 원자를 포함한 3∼10원의 단고리식 또는 이고리식 복소고리아릴, 또는 그 일부 또는 전부가 포화한 것이 바람직하다. 보다 바람직하게는, 1∼4개의 질소 원자, 1∼2개의 산소 원자 및/또는 1개의 유황 원자를 포함한 5∼7원의 단고리식 아릴, 8∼10원의 이고리식 복소고리아릴 또는 그 일부 또는 전부가 포화한 것이다.
본 발명에 있어서는, 특별히 지시하지 않는 한 이성체는 이것을 전부 포함한다. 예컨대, 알킬기, 알콕시기 및 알킬렌기에는 직쇄인 것 및 분지쇄인 것이 포함된다. 또한, 이중 결합, 고리, 축합고리에 있어서의 이성체(E, Z, 시스, 트랜스체), 비대칭 탄소의 존재 등에 의한 이성체(R, S체, α, β체, 거울상이성질체, 부분입체이성질체), 선광성을 갖는 광학 활성체(D, L, d, l체), 크로마토그래프 분리에 의한 극성체(고극성체, 저극성체), 평형 화합물, 이들의 임의의 비율의 혼합물, 라세미 혼합물은 전부 본 발명에 포함된다.
[염]
본 발명에 있어서는 모든 비독성염을 포함한다. 예컨대, 일반적인 염, 산부가염, 수화물염 등을 들 수 있다.
화학식 I로 표시되는 본 발명 화합물은 공지의 방법에 의해 해당하는 염으로 변환할 수 있다. 염은 독성이 없는 수용성의 것이 바람직하다. 적당한 염으로서는, 알칼리 금속(칼륨, 나트륨 등)의 염, 알칼리 토류 금속(칼슘, 마그네슘등)의 염, 암모늄염, 약학적으로 허용되는 유기아민(테트라메틸암모늄, 트리에틸아민, 메틸아민, 디메틸아민, 시클로펜틸아민, 벤질아민, 페네틸아민, 피페리딘, 모노에탄올아민, 디에탄올아민, 트리스(히드록시메틸)아민, 리진, 아르기닌, N-메틸-D-글루카민등)의 염을 들 수 있다.
화학식 I로 표시되는 본 발명 화합물은 공지의 방법에 의해 해당하는 산부가염으로 변환할 수 있다. 산부가염은 독성이 없는 수용성의 것이 바람직하다. 적당한 산부가염으로서는, 염산염, 브롬화수소산염, 황산염, 인산염, 질산염과 같은 무기산염, 또는 초산염, 트리플루오로초산염, 유산염, 타르타르산염, 옥살산염, 푸마르산염, 말레산염, 시트르산염, 안식향산염, 메탄설폰산염, 에탄설폰산염, 벤젠설폰산염, 톨루엔설폰산염, 이세티온산염, 글루쿠론산염, 글루콘산염과 같은 유기산염을 들 수 있다.
또한, 화학식 I로 표시되는 본 발명 화합물 또는 그의 염은 공지의 방법에 의해 수화물로 변환할 수도 있다.
화학식 I로 표시되는 화합물 또는 이들의 비독성염은 전부 바람직하다. 구체적으로는, 실시예에 기재한 화합물 또는 이들의 비독성염을 들 수 있다.
화학식 I로 표시되는 화합물의 4급 암모늄염이란, 화학식 I로 표시되는 화합물의 질소 원자가 R0기에 의해 4급화된 것을 나타낸다.
R0기는 C1∼8 알킬기, 페닐기에 의해 치환된 C1∼8 알킬기를 나타낸다.
화학식 I로 표시되는 화합물의 N-옥사이드란, 화학식 I로 표시되는 화합물의 질소 원자가 산화된 것을 나타낸다.
[본 발명 화합물의 제조 방법]
화학식 I로 표시되는 본 발명 화합물은 이하의 방법 또는 실시예에 기재한방법으로 제조할 수 있다.
화학식 I로 표시되는 본 발명 화합물 중, 질소 원자가 4급 암모늄염 또는 N-옥사이드를 나타내지 않는 화합물, 즉 하기 화학식 I-1로 표시되는 화합물은 이하에 나타낸 방법에 의해 제조할 수 있다.
상기 식에서 R1-1, R2-1, R3-1, R4-1, R5-1은 R1, R2, R3, R4, R5와 동일한 의미를 나타내고, N1은 질소 원자를 나타낸다. 단, 어느 쪽의 질소 원자도 4급 암모늄염 또는 N-옥사이드를 나타내지 않는 것으로 한다.
화학식 I-1 중, R1-1, R2-1, R3-1, R4-1, R5-1기의 어느 것이나 카르복실기, 수산기, 아미노기 또는 티올기를 함유하는 기를 나타내지 않는 화합물, 즉, 하기 화학식 I-1A로 표시되는 화합물은 이하의 방법에 의해 제조할 수 있다.
상기 식에서 R1-1A, R2-1A, R3-1A, R4-1A, R5-1A는 R1-1, R2-1, R3-1, R4-1, R5-1과 동일한 의미를 나타낸다. 단, 모두 카르복실기, 수산기, 아미노기 또는 티올기를 함유하는 기를 나타내지 않는 것으로 하고, 다른 기호는 상기와 동일한 의미를 나타낸다.
화학식 I-1A 중, R1이 수소 원자를 나타내지 않는 화합물, 즉, 하기 화학식 I-1A-1로 표시되는 화합물은 하기 화학식 II-1로 표시되는 화합물 또는 하기 화학식 II-2로 표시되는 화합물을 고리화 반응시킴으로써 제조할 수 있다.
상기 식에서 R1-1A-1은 R1-1A와 동일한 의미를 나타낸다. 단, R1-1A-1은 수소 원자를 나타내지 않는 것으로 하고, 다른 기호는 상기와 동일한 의미를 나타낸다.
상기 식에서 X-L-NH-는 말단 아미노기 폴리스티렌수지의 말단을 나타내고,다른 기호는 상기와 동일한 의미를 나타낸다.
상기 식에서 T는 C1∼8 알킬기, C3∼8의 단고리식 탄소고리, 또는 C3∼8의 단고리식 탄소고리에 의해 치환된 C1∼8 알킬기를 나타낸다.
이 화학식 II-1의 고리화 방법은 공지이며, 예컨대, 유기용매(톨루엔 등) 중, 산(초산, 트리플루오로초산, 염산 등)을 이용하여 60∼120℃로 가열함으로써 행해진다. 이 반응은 폴리스티렌수지의 절단과 동시에 고리화되는 반응이다.
또한 필요하다면, 이 반응에 이어 공지의 방법에 의해 원하는 비독성염으로 변환하는 조작을 행하여도 좋다.
이 화학식 II-2의 고리화 방법은 공지이며, 예컨대, 유기용매(디클로로에탄, 톨루엔 등) 중, 3급 아민(트리에틸아민, 디이소프로필에틸아민 등)을 이용하여 60∼120℃로 가열함으로써 행해진다. 이 반응은 T기의 절단과 동시에 고리화되는 반응이다.
하기 화학식 I-1A 중, R1이 수소 원자를 나타내는 화합물, 즉 하기 화학식 I-1A-2로 표시되는 화합물은 상기한 방법에 의해 제조한 화학식 I-1A-1 중, R1A-1기가 아미노 보호기를 나타내는 화합물, 즉 하기 화학식 I-1A-1-1로 표시되는 화합물을 아미노기의 탈보호 반응시킴으로써 제조할 수 있다.
상기 식에서 모든 기호는 상기와 동일한 의미를 나타낸다.
상기 식에서 R1-1A-1-1은 아미노 보호기를 나타내고, 다른 기호는 상기와 동일한 의미를 나타낸다.
아미노기의 보호기로서는, 예컨대 벤질기, 벤질옥시카르보닐기, 알릴옥시카르보닐기, t-부톡시카르보닐기, 트리플루오로아세틸기 등을 들 수 있다.
아미노기의 보호기로서는, 상기한 것 이외에도 용이하게 또한 선택적으로 이탈할 수 있는 기라면 특별히 한정되지 않는다. 예컨대,T. W. Greene 연구진, Protective Groups in Organic Synthesis, Third Edition, Wiley-Interscience, New York, 1999에 기재된 것이 이용된다.
이 아미노기의 탈보호 반응은 공지이며, 예컨대,
(1) 알칼리 가수분해,
(2) 산성 조건하에 있어서의 탈보호 반응,
(3) 가수소분해에 의한 탈보호 반응,
(4) 금속 착물을 이용하는 탈보호 반응,
이들 방법을 구체적으로 설명하면, (1) 알칼리 가수분해에 의한 탈보호 반응(예컨대, 트리플루오로아세틸기)은, 예컨대, 유기용매(메탄올, 테트라히드로푸란, 디옥산 등) 중, 알칼리 금속의 수산화물(수산화나트륨, 수산화칼륨, 수산화리튬 등), 알칼리 토류 금속의 수산화물(수산화바륨, 수산화칼슘 등) 또는 탄산염(탄산나트륨, 탄산칼륨 등) 혹은 그 수용액 혹은 이들 혼합물을 이용하여 0∼40℃의 온도에서 행해진다.
(2) 산 조건하에서의 탈보호 반응(예컨대, t-부톡시카르보닐기)은, 예컨대, 유기용매(디클로로메탄, 클로로포름, 디옥산, 초산에틸, 아니솔 등) 중, 유기산(초산, 트리플루오로초산, 메탄설폰산 등) 또는 무기산(염산, 황산 등) 혹은 이들의 혼합물(브롬화수소/초산 등) 중 0∼100℃의 온도에서 행해진다.
(3) 가수소분해에 의한 탈보호 반응(예컨대, 벤질기, 벤질옥시카르보닐기, 알릴옥시카르보닐기)은, 예컨대, 용매(에테르계(테트라히드로푸란, 디옥산, 디메톡시에탄, 디에틸에테르 등), 알콜계(메탄올, 에탄올 등), 벤젠계(벤젠, 톨루엔 등),케톤계(아세톤, 메틸에틸케톤 등), 니트릴계(아세토니트릴 등), 아미드계(디메틸포름아미드 등), 물, 초산에틸, 초산 또는 이들 2이상의 혼합용매 등) 중 촉매(팔라듐-탄소, 팔라듐블랙, 수산화팔라듐, 산화백금, 라니-니켈 등)의 존재하에, 상압또는 가압하의 수소 분위기하 또는 포름산암모늄 존재하에 0∼200℃의 온도에서 행해진다.
(4) 금속 착물을 이용하는 탈보호 반응은, 예컨대, 유기용매(디클로로메탄, 디메틸포름아미드, 테트라히드로푸란 등) 중 트랩 시약(수소화트리부틸주석, 디메돈 등) 및/또는 유기산(초산 등)의 존재하에 금속 착물(테트라키스트리페닐포스핀팔라듐(0) 착물 등)를 이용하여 0∼40℃의 온도에서 행해진다.
또한, 화학식 I-1A-1로 표시되는 화합물은 화학식 I-1A-2로 표시되는 화합물을 이용하여 이하의 (a)∼(g)에 나타낸 방법에 의해서도 제조할 수 있다.
(a) 화학식 I-1A-1 중, R1A-1이 C1∼18 알킬기, C2∼18 알케닐기, C2∼18 알키닐기 또는 여러 가지 치환기에 의해 치환된 C1∼18 알킬기, C2∼18 알케닐기, C2∼18 알키닐기를 나타내고, 또한 R1A-1이 N1원자와 결합하는 경우 -CH2-를 통해 결합하는 화합물, 즉 하기 화학식 I-1A-1a로 표시되는 화합물은 화학식 I-1A-2로 표시되는 화합물과 하기 화학식 III로 표시되는 화합물을 환원적 아미노화 반응시킴으로써 제조할 수 있다.
상기 식에서 R1-1A-1a는 C1∼17 알킬기, C2∼17 알케닐기, C2∼17 알키닐기, 또는 임의로 선택된 1∼5개의 (a) 할로겐 원자, (b) -CONR7R8, (c) -COOR9, (d) -OR14, (e) -SR15, (f) -NR16R17, (g) -NR18COR19, (h) -SO2NR20R21, (i) -OCOR22, (j) -NR23SO2R24, (k) -NR25COOR26, (l) -NR27CONR28R29, (m) Cyc1, (n) 케토기, (o) -N(SO2R24)2에 의해 치환된 C1∼17 알킬기, C2∼17 알케닐기 또는 C2∼17 알키닐기를 나타낸다. 단, R1-1A-1a는 카르복실기, 수산기, 아미노기 또는 티올기를 함유하는 기를 나타내지 않는 것으로 하고, 다른 기호는 상기와 동일한 의미를 나타낸다.
상기 식에서 모든 기호는 상기와 동일한 의미를 나타낸다.
이 환원적 아미노화 반응은 공지이며, 예컨대, 유기용매(예컨대, 디클로로에탄, 디클로로메탄, 디메틸포름아미드, 초산 및 이들의 혼합물 등) 중 환원제(수소화트리아세톡시붕소나트륨, 시아노수소화붕소나트륨 등)의 존재하에 0∼40℃의 온도에서 행해진다.
또한, 이 환원적 아미노화 반응은 R1기 중의 질소 원자가 N-옥사이드를 나타내는 화합물에 있어서도 행할 수 있다.
(b) 화학식 I-1A-1 중, R1A-1이 C1∼18 알킬기, C2∼18 알케닐기, C2∼18 알키닐기 또는 여러 가지 치환기에 의해 치환된 C1∼18 알킬기, C2∼18 알케닐기, C2∼18 알키닐기를 나타내고, 또한 R1A-1이 N1원자와 결합하는 경우 -CHRA-1b-(기 중, RA-1b는 C1∼17 알킬기, C2∼17 알케닐기, C2∼17 알키닐기를 나타냄)를 통해 결합하는 화합물, 즉 하기 화학식 I-1A-1b로 표시되는 화합물은 화학식 I-1A-2로 표시되는 화합물과 하기 화학식 IV로 표시되는 화합물을 환원적 아미노화 반응시킴으로써 제조할 수 있다.
상기 식에서 RA-1b는 C1∼17 알킬기, C2∼17 알케닐기, C2∼17 알키닐기를 나타내고, 다른 기호는 상기와 동일한 의미를 나타낸다.
상기 식에서 모든 기호는 상기와 동일한 의미를 나타낸다.
이 환원적 아미노화 반응은 공지이며, 예컨대, 유기용매(예컨대, 디클로로에탄, 디클로로메탄 등) 중 3급 아민(트리에틸아민, 디이소프로필에틸아민 등)의 존재하에 루이스산(사염화티탄 등)을 이용하여 0∼40℃에서 반응시키고, 또한, 환원제(수소화트리아세톡시붕소나트륨, 시아노수소화붕소나트륨 등)의 존재하에 0∼40℃의 온도에서 행해진다.
(c) 화학식 I-1A-1 중, R1A-1이 COR6을 나타내는 화합물, 즉 하기 화학식 I-1A-1c로 표시되는 화합물은 화학식 I-1A-2로 표시되는 화합물과 하기 화학식 V로 표시되는 화합물을 아미드화 반응시킴으로써 제조할 수 있다.
상기 식에서 R6-1A-1c는 R6과 동일한 의미를 나타낸다. 단, R6-1A-1c는 카르복실기, 수산기, 아미노기 또는 티올기를 함유하는 기를 나타내지 않는 것으로 하고, 또한 어느 쪽의 질소 원자도 4급 암모늄염 또는 N-옥사이드를 나타내지 않는 것으로 하며, 다른 기호는 상기와 동일한 의미를 나타낸다.
상기 식에서 모든 기호는 상기와 동일한 의미를 나타낸다.
이 아미드화 반응은 공지이며, 유기용매(클로로포름, 디클로로메탄, 디에틸에테르, 테트라히드로푸란, 디옥산, 디메틸포름아미드 등) 중 3급 아민(이소프로필에틸아민, 피리딘, 트리에틸아민, 디메틸아닐린, 디메틸아미노피리딘 등) 혹은 알칼리 수용액(중조수 또는 수산화나트륨 용액 등)의 존재하에 0∼40℃에서 반응시킴으로써 행해진다.
(d) 화학식 I-1A-1 중, R1-1A-1이 SO2R10을 나타내는 화합물, 즉 하기 화학식 I-1A-1d로 표시되는 화합물은 화학식 I-1A-2로 표시되는 화합물과 하기 화학식 VI로 표시되는 화합물을 설폰아미드화 반응시킴으로써 제조할 수 있다.
상기 식에서 R10-1A-1d는 R10과 동일한 의미를 나타낸다. 단, 카르복실기, 수산기, 아미노기 또는 티올기를 함유하는 기를 나타내지 않는 것으로 하고, 또한 어느 쪽의 질소 원자도 4급 암모늄염 또는 N-옥사이드를 나타내지 않는 것으로 하며, 다른 기호는 상기와 동일한 의미를 나타낸다.
상기 식에서 모든 기호는 상기와 동일한 의미를 나타낸다.
이 설폰아미드화 반응은 공지이며, 불활성 유기용매(클로로포름, 디클로로메탄, 디클로로에탄, 디에틸에테르, 테트라히드로푸란 등) 중 3급 아민(디이소프로필에틸아민, 피리딘, 트리에틸아민, 디메틸아닐린, 디메틸아미노피리딘 등)의 존재하에 0∼40℃에서 반응시킴으로써 행해진다.
(e) 화학식 I-1A-1 중, R1A-1이 CONR7R8을 나타내는 화합물, 즉 하기 화학식I-1A-1e로 표시되는 화합물은 화학식 I-1A-2로 표시되는 화합물과 하기 화학식 VII-1로 표시되는 화합물 또는 하기 화학식 VII-2로 표시되는 화합물을 반응시킴으로써 제조할 수 있다.
상기 식에서 R7-1A-1e및 R8-1A-1e는 R7및 R8과 동일한 의미를 나타낸다. 단, 모두 카르복실기, 수산기, 아미노기 또는 티올기를 함유하는 기를 나타내지 않는 것으로 하고, 또한 어느 쪽의 질소 원자도 4급 암모늄염 또는 N-옥사이드를 나타내지 않는 것으로 하며, 다른 기호는 상기와 동일한 의미를 나타낸다.
상기 식에서 모든 기호는 상기와 동일한 의미를 나타낸다.
상기 식에서 모든 기호는 상기와 동일한 의미를 나타낸다.
이 화학식 VII-1과의 반응은 공지이며, 유기용매(클로로포름, 디클로로메탄, 디에틸에테르, 테트라히드로푸란 등) 중 3급 아민(이소프로필에틸아민, 피리딘, 트리에틸아민, 디메틸아닐린, 디메틸아미노피리딘 등)의 존재하에 0∼40℃에서 반응시킴으로써 행해진다.
이 화학식 VII-2와의 반응은 공지이며, 불활성 유기용매(클로로포름, 디클로로메탄, 디클로로에탄, 디메틸포름아미드, 디에틸에테르, 테트라히드로푸란 등) 중, 0∼40℃에서 반응시킴으로써 행해진다.
(f) 화학식 I-1A-1 중, R1-1A-1이 -CH2-CH(OH)-RA-1f(RA-1f는 C1∼16 알킬기, C2∼16 알케닐기, C2∼16 알키닐기 또는 여러 가지 치환기에 의해 치환된 C1∼16 알킬기, C2∼16 알케닐기, C2∼16 알키닐기를 나타냄)를 나타내는 화합물, 즉 하기 화학식 I-1A-1f로 표시되는 화합물은 화학식 I-1A-2로 표시되는 화합물과 하기 화학식 VIII로 표시되는 화합물을 반응시킴으로써 제조할 수 있다.
상기 식에서 RA-1f는 C1∼16 알킬기, C2∼16 알케닐기, C2∼16 알키닐기 또는 임의로 선택된 1∼4개의 (a) 할로겐 원자, (b) -CONR7R8, (c) -COOR9, (d) -OR14, (e) -SR15, (f) -NR16R17, (g) -NR18COR19, (h) -SO2NR20R21, (i) -OCOR22, (j) -NR23SO2R24, (k) -NR25COOR26, (l) -NR27CONR28R29, (m) Cyc1, (n) 케토기, (o) -N(SO2R24)2에 의해 치환된 C1∼16 알킬기, C2∼16 알케닐기, C2∼16 알키닐기를 나타내고, 또한 어느 쪽의 질소 원자도 4급 암모늄염 또는 N-옥사이드를 나타내지 않는 것으로 하며, 다른 기호는 상기와 동일한 의미를 나타낸다.
상기 식에서 모든 기호는 상기와 동일한 의미를 나타낸다.
이 반응은 공지이며, 유기용매(메탄올, 에탄올, 2-프로판올, 테트라히드로푸란, 아세토니트릴 등) 중, 3급 아민(트리에틸아민, N-메틸모르폴린 등)의 존재하 또는 비존재하에 40∼100℃에서 반응시킴으로써 행해진다.
(g) 화학식 I-1A-1 중, R1-1A-1이 -CH2-C(=O)-RA-1g(RA-1g는 RA-1f와 동일한 의미를 나타냄)를 나타내는 화합물, 즉 하기 화학식 I-1A-1g로 표시되는 화합물은 화학식 I-1A-2로 표시되는 화합물과 하기 화학식 IX-1로 표시되는 화합물 또는 하기 화학식 IX-2로 표시되는 화합물을 반응시킴으로써 제조할 수 있다.
상기 식에서 RA-1g는 RA-1f와 동일한 의미를 나타내고, 다른 기호는 상기와 동일한 의미를 나타낸다.
상기 식에서 모든 기호는 상기와 동일한 의미를 나타낸다.
상기 식에서 모든 기호는 상기와 동일한 의미를 나타낸다.
이들의 반응은 공지이며, 유기용매(클로로포름, 디클로로메탄, 디에틸에테르, 테트라히드로푸란, 디옥산, 디메틸포름아미드 등) 중 3급 아민(이소프로필에틸아민, 피리딘, 트리에틸아민, 디메틸아닐린, 디메틸아미노피리딘 등)의 존재하에 0∼40℃에서 반응시킴으로써 행해진다.
또한, 화학식 I-1A-1로 표시되는 화합물은 이하의 (h)에 나타낸 방법에 의해서도 제조할 수 있다.
(h) 화학식 I-1A-1 중, R1-1A-1이 2-프로페닐기(-CH2CH=CH2)를 나타내는 화합물, 즉 하기 화학식 I-1A-1h로 표시되는 화합물은 상기한 방법에 의해 제조한 화학식 I-1A-1 중, R1-1A-1기가 2-프로페닐옥시카르보닐기(-COO-CH2CH=CH2)를 나타내는 화합물, 즉 하기 화학식 I-1A-1-2로 표시되는 화합물을 금속 착물을 이용하는 반응에 부침으로써 제조할 수 있다.
상기 식에서 모든 기호는 상기와 동일한 의미를 나타낸다.
상기 식에서 모든 기호는 상기와 동일한 의미를 나타낸다.
이 금속 착물을 이용하는 반응은 공지이며, 예컨대, 유기용매(테트라히드로푸란, 초산 등) 중, 금속 착물(테트라키스트리페닐포스핀팔라듐(0) 착물 등)를 이용하여 0∼40℃의 온도에서 행해진다.
화학식 I-1 중, R1, R2, R3, R4, R5기의 적어도 하나의 기가 카르복실기, 수산기, 아미노기 또는 티올기를 함유하는 기를 나타내는 화합물, 즉, 하기 화학식 I-1B로 표시되는 화합물은 상기한 방법에 의해 제조한 화학식 I-1A 중, R1-1, R2-1, R3-1, R4-1, R5-1의 적어도 하나의 기가 보호기에 의해 보호된 카르복실기, 수산기, 아미노기 또는 티올기를 함유하는 기를 나타내는 화합물, 즉, 하기 화학식 I-1A-3으로 표시되는 화합물을 보호기의 탈보호 반응에 부침으로써 제조할 수 있다.
상기 식에서 R1-1B, R2-1B, R3-1B, R4-1B, R5-1B는 R1-1, R2-1, R3-1, R4-1, R5-1과 동일한 의미를 나타낸다. 단, 적어도 하나의 기가 카르복실기, 수산기, 아미노기 또는 티올기를 함유하는 기를 나타내고, 다른 기호는 상기와 동일한 의미를 나타낸다.
상기 식에서 R1-1A-3, R2-1A-3, R3-1A-3, R4-1A-3, R5-1A-3은 R1-1, R2-1, R3-1, R4-1, R5-1과 동일한 의미를 나타낸다. 단, 적어도 하나의 기가 보호기에 의해 보호된 카르복실기, 수산기, 아미노기 또는 티올기를 함유하는 기를 나타내고, 다른 기호는 상기와 동일한 의미를 나타낸다.
카르복실기의 보호기로서는, 예컨대 메틸기, 에틸기, t-부틸기, 벤질기, 알릴기를 들 수 있다.
수산기의 보호기로서는, 예컨대 메톡시메틸기, 2-테트라히드로피라닐기, t-부틸디메틸실릴기, t-부틸디페닐실릴기, 아세틸기, 벤질기를 들 수 있다.
아미노기의 보호기로서는, 예컨대 벤질옥시카르보닐기, 알릴옥시카르보닐기, t-부톡시카르보닐기, 트리플루오로아세틸기, 9-플루오레닐메톡시카르보닐기를 들 수 있다.
티올기의 보호기로서는, 예컨대 벤질기, 메톡시벤질기, 아세트아미드메틸기,트리페닐메틸기, 아세틸기를 들 수 있다.
카르복실기, 수산기, 아미노기 또는 티올기의 보호기로서는, 상기한 이외에도 용이하게 또한 선택적으로 이탈할 수 있는 기라면 특별히 한정되지 않는다. 예컨대,T. W. Greene 연구진, Protective Groups in Organic Synthesis, Third Edition, Wiley-Interscience, New York, 1999에 기재된 것이 이용된다.
아미노기의 보호기의 탈보호 반응은 상기한 방법에 의해 행해진다.
카르복실기, 수산기 또는 티올기의 보호기의 탈보호 반응은 잘 알려져 있고, 예컨대 다음과 같은 반응 등을 들 수 있다.
(1) 알칼리 가수분해
(2) 산성 조건하에 있어서의 탈보호 반응
(3) 가수소분해에 의한 탈보호 반응
(4) 실릴기의 탈보호 반응
(5) 금속 착물을 이용하는 탈보호 반응
이들 방법 중, (1), (2), (3), (5)는 상기한 아미노기의 보호기의 탈보호 반응과 같은 방법에 의해 행해진다.
(4)를 구체적으로 설명하면, 실릴기의 탈보호 반응은, 예컨대, 유기용매(테트라히드로푸란, 아세토니트릴 등) 중, 테트라부틸암모늄플루오라이드를 이용하여 0∼40℃의 온도에서 행해진다.
당업자는 용이하게 이해할 수 있는 것이기는 하지만, 이들 탈보호 반응을 구별지어 사용함으로써 목적으로 하는 본 발명 화합물을 용이하게 제조할 수 있다.
또한, 화학식 I-1A-1로 표시되는 화합물은 하기 화학식 I-1B-1로 표시되는 화합물을 이용하여 이하의 (j)∼(m)에 나타낸 방법에 의해서도 제조할 수 있다.
상기 식에서 R1-1B-1, R2-1B-1, R3-1B-1, R4-1B-1, R5-1B-1은 R1-1, R2-1, R3-1, R4-1, R5-1과 동일한 의미를 나타낸다. 단, 적어도 하나의 기가 아미노기를 함유하는 기를 나타내고, 다른 기호는 상기와 동일한 의미를 나타낸다.
(j) 화학식 I-1A-1 중, R1-1A-1, R2-1A, R3-1A, R4-1A, R5-1A의 적어도 하나의 기가 아미드기를 함유하는 기를 나타내는 화합물, 즉 하기 화학식 I-1A-1j로 표시되는 화합물은 화학식 I-1B-1로 표시되는 화합물을 아미드화 반응시킴으로써 제조할 수 있다.
상기 식에서 R1-1A-1j, R2-1A-1j, R3-1A-1j, R4-1A-1j, R5-1A-1j는 R1-1, R2-1, R3-1, R4-1,R5-1과 동일한 의미를 나타낸다. 단, 적어도 하나의 기가 아미드기를 함유하는 기를 나타내고, 다른 기호는 상기와 동일한 의미를 나타낸다.
이 아미드화 반응은 상기한 방법에 의해 행할 수 있다.
(k) 화학식 I-1A-1 중, R1-1A-1, R2-1A, R3-1A, R4-1A, R5-1A의 적어도 하나의 기가 설폰아미드기를 함유하는 기를 나타내는 화합물, 즉 하기 화학식 I-1A-1k로 표시되는 화합물은 화학식 I-1B-1로 표시되는 화합물을 설폰아미드화 반응시킴으로써 제조할 수 있다.
상기 식에서 R1-1A-1k, R2-1A-1k, R3-1A-1k, R4-1A-1k, R5-1A-1k는 R1-1, R2-1, R3-1, R4-1, R5-1과 동일한 의미를 나타낸다. 단, 적어도 하나의 기가 설폰아미드기를 함유하는 기를 나타내고, 다른 기호는 상기와 동일한 의미를 나타낸다.
이 설폰아미드화 반응은 상기한 방법에 의해 행할 수 있다.
(m) 화학식 I-1A-1 중, R1-1A-1, R2-1A, R3-1A, R4-1A, R5-1A중 적어도 하나의 기가 우레아기를 함유하는 기를 나타내는 화합물, 즉 하기 화학식 I-1A-1m으로 표시되는 화합물은 화학식 I-1B-1로 표시되는 화합물을 우레아화 반응시킴으로써 제조할 수있다.
상기 식에서 R1-1A-1m, R2-1A-1m, R3-1A-1m, R4-1A-1m, R5-1A-1m은 R1-1, R2-1, R3-1, R4-1, R5-1과 동일한 의미를 나타낸다. 단, 적어도 하나의 기가 우레아기를 함유하는 기를 나타내고, 다른 기호는 상기와 동일한 의미를 나타낸다.
이 우레아화 반응은 상기한 방법에 의해 행할 수 있다.
화학식 I-1 중, R1-1, R2-1, R3-1, R4-1, R5-1기의 적어도 하나의 기가 수산기를 함유하는 기를 나타내거나 및/또는 R1가 카르복시기를 함유하는 기를 나타내는 화합물, 즉, 하기 화학식 I-1B-2로 표시되는 화합물은 이하의 (n)의 방법에 의해서도 제조할 수 있다.
상기 식에서 R1-1B-2, R2-1B-2, R3-1B-2, R4-1B-2, R5-1B-2는 R1-1, R2-1, R3-1, R4-1, R5-1과동일한 의미를 나타낸다. 단, R1-1B-2, R2-1B-2, R3-1B-2, R4-1B-2, R5-1B-2기 중 적어도 하나의 기가 수산기를 함유하는 기를 나타내거나 및/또는 R1B-2가 카르복시기를 함유하는 기를 나타내고, 다른 기호는 상기와 동일한 의미를 나타낸다.
(n) 화학식 I-1B-2 중, R1-1B-2가 C1∼18 알킬기, C2∼18 알케닐기, C2∼18 알키닐기 또는 여러 가지 치환기에 의해 치환된 C1∼18 알킬기, C2∼18 알케닐기, C2∼18 알키닐기를 나타내고, 또한 R1-1B-2가 N1원자와 결합하는 경우 -CH2-를 통해 결합하는 화합물, 즉 하기 화학식 I-1B-1n으로 표시되는 화합물은 상기한 방법에 의해 제조한 화학식 I-1B 중, R1이 수소 원자를 나타내고, R2-1, R3-1, R4-1, R5-1중 적어도 하나의 기가 수산기를 함유하는 기를 나타내는 화합물, 즉, 하기 화학식 I-1B-3으로 표시되는 화합물과 하기 화학식 X로 표시되는 화합물을 환원적 아미노화 반응시킴으로써 제조할 수 있다.
상기 식에서 R1-1B-2n은 C1∼17 알킬기, C2∼17 알케닐기, C2∼17 알키닐기 또는 임의로 선택된 1∼5개의 (a) 할로겐 원자, (b) -CONR7R8, (c) -COOR9, (d) -OR14,(e) -SR15, (f) -NR16R17, (g) -NR18COR19, (h) -SO2NR20R21, (i) -OCOR22, (j) -NR23SO2R24, (k) -NR25COOR26, (l) -NR27CONR28R29, (m) Cyc1, (n) 케토기, (o) -N(SO2R24)2에 의해 치환된 C1∼17 알킬기, C2∼17 알케닐기 또는 C2∼17 알키닐기를 나타낸다. 단, R1-1B-2n, R2-1B-2, R3-1B-2, R4-1B-2, R5-1B-2기 중 적어도 하나의 기가 수산기를 함유하는 기를 나타내거나 및/또는 R1B-2n이 카르복시기를 함유하는 기를 나타내고, 또한 어느 쪽의 질소 원자도 4급 암모늄염 또는 N-옥사이드를 나타내지 않는 것으로 하며, 다른 기호는 상기와 동일한 의미를 나타낸다.
상기 식에서 모든 기호는 상기와 동일한 의미를 나타낸다.
상기 식에서 모든 기호는 상기와 동일한 의미를 나타낸다.
이 환원적 아미노화 반응은 상기한 방법에 의해 행해진다.
또한, 이 환원적 아미노화 반응은 R1기 중의 질소 원자가 N-옥사이드를 나타내는 화합물에 있어서도 행할 수 있다.
화학식 I로 표시되는 본 발명 화합물 중, 적어도 하나의 질소 원자가 4급 암모늄염을 나타내는 화합물, 즉 하기 화학식 I-2로 표시되는 화합물은 화학식 I-1로 표시되는 화합물과 하기 화학식 XI로 표시되는 화합물을 반응시킴으로써 제조할 수 있다.
상기 식에서 R1-2, R2-2, R3-2, R4-2, R5-2는 R1, R2, R3, R4, R5와 동일한 의미를 나타내고, N2는 질소 원자를 나타낸다. 단, 적어도 하나의 질소 원자가 4급 암모늄염을 나타내는 것으로 하고, Q는 할로겐 원자를 나타내는 것으로 한다.
상기 식에서 R0은 C1∼8 알킬기 또는 페닐기에 의해 치환된 C1∼8 알킬기를 나타내고, Q는 할로겐 원자를 나타낸다.
이 반응은 공지이며, 예컨대, 유기용매(아세톤, 디메틸포름아미드, 메틸에틸케톤 등) 중, 0∼40℃의 온도에서 행해진다.
화학식 I로 표시되는 본 발명 화합물 중, 적어도 하나의 질소 원자가 N-옥사이드를 나타내는 화합물, 즉 하기 화학식 I-3으로 표시되는 화합물은 화학식 I-1로 표시되는 화합물을 산화 반응시킴으로써 제조할 수 있다.
상기 식에서 R1-3, R2-3, R3-3, R4-3, R5-3은 R1, R2, R3, R4, R5와 동일한 의미를 나타내고, N3은 질소 원자를 나타낸다. 단, 적어도 하나의 질소 원자가 N-옥사이드를 나타내는 것으로 한다.
이 산화 반응은 공지이며, 예컨대, 적당한 유기용매(디클로로메탄, 클로로포름, 벤젠, 헥산, t-부틸알콜 등) 중에서, 과산화제(과산화수소, 과요오드산나트륨, 아질산아실, 과붕산나트륨, 과산(예컨대, 3-클로로과벤조산, 과초산 등), 옥손(상품명, 이하, 옥손이라 약기함; 과산화모노황산칼륨), 과망간산칼륨, 크롬산 등)의 존재하에 20∼60℃의 온도에서 반응시킴으로써 행해진다.
화학식 II-1로 표시되는 화합물은 다음에 도시하는 반응식 1∼3에 의해 제조할 수 있다.
반응식 중, X는 폴리스티렌수지를 나타내고, L은 2가기를 나타내며, 그 밖의 기호는 상기와 동일한 의미를 나타낸다.
L이 나타내는 2가기란, 이용하는 수지에 따라 다르지만, 예컨대, 메틸렌기, Rink기를 들 수 있다. Rink기란, 4-(2,4-디메톡시벤질)페녹시메틸기를 의미한다.
본 발명에 있어서, 말단 아미노기 폴리스티렌수지로서는, 예컨대, 아미노메틸폴리스티렌수지, 9-플루오레닐메틸옥시카르보닐아미노-Rink수지 등이 사용된다.
다음 반응식 4에 도시한 바와 같이, 아미노메틸폴리스티렌수지, 9-플루오레닐메틸옥시카르보닐아미노-Rink수지를 이용하여 화학식 XVI로 표시되는 수지를 제조할 수 있다.
본 발명 중의 폴리스티렌수지를 이용한 반응에 있어서는, 반응생성물은 통상의 정제 수단, 예컨대, 용매(디메틸포름아미드, 디클로로메탄, 메탄올, 테트라히드로푸란, 톨루엔, 초산/톨루엔 등)로 복수 회 세정함으로써 정제할 수 있다. 또한, 최종 반응의 생성물은 통상의 정제 수단, 예컨대, 상압하 또는 감압하에 있어서의 증류, 실리카겔 또는 규산마그네슘을 이용한 고속 액체 크로마토그래피, 박층 크로마토그래피, 혹은 칼럼 크로마토그래피 또는 세정, 재결정 등의 방법에 의해 정제할 수 있다.
또한, 화학식 II-2로 표시되는 화합물은 다음에 도시하는 반응식 5에 의해 제조할 수 있다.
본 발명에 있어서의 출발 물질 및 각 시약은 그 자체가 공지이거나 또는 공지의 방법에 의해 제조할 수 있다.
[약리활성]
화학식 I로 표시되는 본 발명 화합물의 유효성은 예컨대 이하의 실험에 의해서 증명되었다.
전술한 바와 같이, HIV가 CD4 양성 세포상의 수용체인 CXCR4 혹은 CCR5에 결합하는 것을 억제하는 화합물을 스크리닝하기 위해서는 HIV 바이러스를 이용한 분석계에서 행하는 것이 보다 직접적인 수법이다. 그러나, HIV 바이러스를 대량 스크리닝에 사용하기 위해서는 그 취급의 어려움 때문에 실용적이지 못하다. 한편, 대식세포 지향성(R5) HIV-1과 RANTES, MIP-1α, MIP-1β가 모두 CCR5에 결합함으로써 HIV측과 RANTES, MIP-1α, MIP-1β측 쌍방의 CCR5 결합 부위 및 CCR5측의 RANTES, MIP-1α, MIP-1β 및 HIV 결합 부위에는 어떠한 공통되는 특징이 있는 것으로 예측할 수 있다. 따라서, 기존의 항AIDS약(역전사 억제제나 프로테아제 억제)과 다른 작용기순서인 HIV 바이러스의 세포에의 흡착을 억제하는 화합물을 발견하기 위해서 HIV 대신에 CCR5의 내인성 리간드인 RANTES, MIP-1α, MIP-1β를 이용한 분석계를 이용할 수 있다.
구체적으로는, RANTES와 CCR5의 결합을 억해하는 화합물을 스크리닝하는 계로서, 예컨대, CCR5는 G 단백질 공역 7회 막 관통형 수용체이기 때문에, RANTES가 CCR5를 통해 유도하는 Ca 이온의 일과성 상승에 대한 효과를 측정하는 계를 실시할 수 있다. T 세포 지향성(X4)HIV와 SDF-1이 모두 CXCR4에 결합함으로써 동일한 사고 방식이 가능하다.
[실험방법]
(1) 인간 CCR5 유전자의 단리
인간 태반 cDNA는 Marathon cDNA amplification kit(Clontech)를 이용하여 제작하였다. PCR 프라이머인 hCCR5XbaI-F1: 5'-AGCTAGTCTAGATCCGTTCCCCTACAAGAAACTCTCC-3'(서열 번호 1) 및 hCCR5XbaI-R': 5'-AGCTAGTCTAGAGTGCACAACTCTGACTGGGTCACCA-3'(서열 번호 2)는 GenBank U54994의 서열에 기하여 설계하였다.
인간 태반 cDNA를 주형으로 하고, Ex Taq(Takara)를 이용하여 PCR 반응(95℃에서 2분→[95℃에서 30초, 60℃에서 45초, 72℃에서 1분]×35회)을 행하였다. 증폭시킨 PCR 산물을 1% 아가로즈 겔 전기 영동한 후, QIAquick Gel Extraction Kit(QIAGEN)를 이용하여 정제하고, 제한 효소 XbaI로 절단하였다. 절단한 단편을 발현 벡터 pEF-BOS-bsr에 DNA Ligation Kit Ver.2(Takara)를 이용하여 연결하고, 대장균 DH5a로 형질 전환하였다. 이 플라스미드 pEF-BOS-bsr/hCCR5를 조제하여 DNA 서열을 확인하였다.
(2) CHO 세포의 배양
CHO-dhfr(-)는 Ham's F-12(소 태아 혈청(10%), 페니실린(50 U/ml), 스트렙토마이신(50 mg/ml) 함유)를 이용하여 배양하였다. 또한, 형질 도입한 세포는 상기에 블라스토사이딘(5 mg/ml)을 첨가하여 배양하였다.
(3) CHO 세포에의 형질 도입
DMRIE-C reagent(Gibco BRL)를 이용하여 플라스미드 pEF-BOS-bsr/hCCR5를 CHO-dhfr(-) 세포에 형질 도입하였다. 48시간 후, 5 mg/ml의 블라스토사이딘을 포함한 배지로 교환하여 선택을 행하고, 안정 과발현 세포를 수립하였다.
(4) RANTES와 CCR5의 결합(RANTES의 Ca 이온 일과성 상승 유도 활성)에 대한 억제 실험
수립한 인간 CCR5 안정 과발현 CHO 세포(CCR5/CHO 세포)를 Ham's F-12 배지 및 FBS(10%)에 현탁하고, 96 웰 플레이트에 3.0×106세포/웰이 되도록 하였다. 37℃에서 1일 배양한 후, 배양 상청액을 제거하고, Ham's F-12 배지(Fura-2 AM(5 μM), Probenecid(2.5 mM) 및 HEPES(20 mM; pH 7.4) 함유)를 80 μl/웰 첨가하여, 차광 상태로, 37℃에서 1시간 항온배양하였다. 1×Hanks/HEPES(20 mM; pH 7.4) 용액으로 2회 세정한 후, 동 용액을 100 μl/웰 첨가하였다. 이 Fura-2 AM을 받아들인 CCR5/CHO 세포에 대하여, 시험 화합물을 첨가한 후 3분 경과시에 1×Hanks/HEPES(20 mM; pH 7.4) 용액으로 희석한 재조합 인간 RANTES(PeproTech)를 최종 농도 10 nM로 첨가하였다. 인간 RANTES에 의해 유도되는 세포내 Ca2+농도의 일과성 상승을 96웰용 Ca2+검출기(하마마쯔포토닉스)를 이용하여 측정하고, 시험 화합물의 억제율(%)을 이하의 계산식에 의해 산출하였다.
억제율=(Ec-Ea)/Ec×100
Ec: RANTES에 의한 Ca2+일과성 상승의 측정치
Ea: 시험 화합물을 첨가했을 때의 RANTES에 의한 Ca2+일과성 상승의 측정치
그 결과, 본 발명 화합물은 10 μM에서 50% 이상의 억제를 나타내었다. 예컨대, 실시예 2(1) 화합물은 IC50치가 0.05 μM, 실시예 2(2) 화합물은 IC50치가 0.05 μM였다.
CCR5 지향성의 HIV주에 대하여 흡착 억제 효과를 갖는 화합물을 발견하는 계에 관해서는 상술하였지만, 이 계를 이용하여 CCR5 혹은 그 리간드의 작용을 억제하는 화합물도 발견하는 것은 당연히 가능하다. 마찬가지로, 다른 케모카인 수용체와 그 리간드의 작용을 억제하는 화합물을 발견하는 것이 가능하다. 예컨대, CCR2 혹은 그 리간드의 작용을 억제하는 화합물을 발견하는 계도 구축할 수 있다. CCR5와 같이 CCR2는 G 단백질 공역 7회 막 관통형 수용체이기 때문에, 그 리간드가 존재한다. 예컨대 MCP-1이 CCR2를 통해 유도하는 Ca 이온의 일과성 상승에 대한 효과를 측정함으로써 실시할 수 있다.
(5) MCP-1과 CCR2의 결합(MCP-1의 Ca 이온 일과성 상승 유도 활성)에 대한 억제 실험
인간 CCR2를 발현한 세포, 예컨대 인간 단구 세포주 THP-1(ATCC No. TIB-202)을 FBS(10%), Fura2-AM(5 μM), Probenecid(2.5 mM) 및 HEPES(20 mM, pH 7.4)를 포함하는 RPMI1640 배지에 5.0×106세포/ml가 되도록 현탁하고 차광한 상태로 37℃에서 30분간 보온하였다. 4∼8배의 1×Hanks/HEPES(20 mM, pH 7.4)/Probenecid(2.5 mM)를 첨가하고 차광한 상태로 37℃에서 30분간 더 보온하였다. 1×Hanks/HEPES(20 mM, pH 7.4)/Probenecid(2.5 mM) 용액으로 세포를 세정한 후, 동 용액으로 2.0×106세포/ml을 재현탁하여 96 웰 플레이트에 100 μl 첨가하였다. 시험 화합물 용액을 첨가한 후, 3분 경과시에 1×Hanks/HEPES(20 mM, pH 7.4)/Probenecid(2.5 mM)로 희석한 재조합 인간 MCP-1(PeproTech)을 최종 농도 30nM로 첨가하였다. 인간 MCP-1에 의해 유도되는 세포내 Ca2+농도의 일과성 상승을 96웰용 Ca2+검출기(하마마쯔포토닉스)를 이용하여 측정하고, 시험 화합물의 억제율(%)을 이하의 계산식에 의해 산출하였다.
억제율=(Ec-Ea)/Ec×100
Ec: MCP-1에 의한 Ca2+일과성 상승의 측정치
Ea: 시험 화합물을 첨가했을 때의 MCP-1에 의한 Ca2+일과성 상승의 측정치
그 결과, 본 발명 화합물은 10 μM에서 50% 이상의 억제를 나타내었다. 예컨대, 실시예 5(2) 화합물은 IC50치가 3 μM였다.
[독성]
본 발명 화합물의 독성은 매우 낮고, 의약으로서 사용하기 위해서 충분히 안전하다고 판단할 수 있다.
이하, 참고예 및 실시예에 의해 본 발명을 상세히 설명하지만, 본 발명은 이들에 한정되지 않는다.
크로마토그래피에 의한 분리의 개소 및 TLC에 표시되어 있는 괄호 안의 용매는 사용한 용출 용매 또는 전개 용매를 나타내고, 비율은 체적비를 나타낸다.
NMR 개소에 표시되어 있는 괄호 안의 용매는 측정에 사용한 용매를 나타내고 있다.
R*과 S*는 절대 위치를 나타내지 않고 상대 위치만을 나타낸다.
참고예 1: 수지(2)의 합성
아미노메틸폴리스티렌수지·염산염(수지(1); X는 폴리스티렌수지를 나타냄)(30.0 g)(1% 디비닐벤젠 공중합체, 와타나베카가꾸사에서 제조, 카탈로그 번호 A00062)을 디메틸포름아미드(300 ml), 10% 디이소프로필에틸아민-디메틸포름아미드 용액(300 ml) 및 디메틸포름아미드(300 ml)로 순차 세정하고, 디메틸포름아미드(200 ml)에 현탁하였다. 현탁액에 포름산(10.2 ml) 및 디이소프로필카르보디이미드(42.3 ml)를 빙냉하에서 첨가하여 실온에서 1시간 교반하였다. 반응 용액으로부터 수지를 여과하여 취하고, 디메틸포름아미드(250 ml×3회), 디클로로메탄(250 ml×4회), 메탄올(250 ml×2회) 및 디클로로메탄(250 ml×4회)으로 세정하여 수지(2)를 얻었다.
IR(KBr): ν 1682 cm-1.
참고예 2: 수지(3)의 합성
참고예 1에서 얻은 수지(2)의 디클로로메탄(300 ml) 현탁액에 트리에틸아민(18.8 ml), 사염화탄소(13.0 ml) 및 트리페닐포스핀(35.4 g)을 첨가하여 1시간 가열 환류하였다. 반응 용액을 실온에서 냉각시킨 후, 수지를 여과하여 취하였다. 수지를 디클로로메탄(250 ml×3회), 메탄올(250 ml×1회) 및 디클로로메탄(250 ml×2회)으로 세정하고, 감압 건조하여 수지(3)(28.2 g)를 얻었다.
IR(KBr): ν 2147 cm-1.
참고예 3: 화합물(1)의 합성
참고예 2에서 제조한 수지(3)(2.5 g)의 테트라히드로푸란/메탄올(1:1;25 ml)의 현탁액에 N-알릴옥시카르보닐-4-피페리돈(2.15 g), n-프로필아민(0.97 ml) 및 N-(t-부틸옥시카르보닐)류신(2.93 g)을 첨가하고 65℃에서 16시간 교반하였다. 반응 용액을 실온에서 냉각시키고, 수지를 여과하여 취하였다. 얻어진 수지를 테트라히드로푸란(25 ml×2회), 메탄올(25 ml×2회) 및 디클로로메탄(25 ml×2회)으로 세정하여 화합물(1)을 얻었다.
참고예 4: 화합물(2)의 합성
참고예 3에서 제조한 화합물(1)의 디클로로메탄(25 ml) 현탁액에 초산(0.81 ml), 수소화트리부틸주석(1.90 ml) 및 테트라키스트리페닐포스핀팔라듐(0) 착물(270 mg)를 첨가하여 실온에서 6시간 교반하였다. 반응 용액으로부터 수지를 여과하여 취하고, 디클로로메탄(25 ml×3회), 메탄올(25 ml×2회),디클로로메탄(25 ml×2회) 및 디메틸포름아미드(25 ml×3회)로 세정하여 화합물(2)을 얻었다.
참고예 5: 화합물(3)의 합성
참고예 4에서 제조한 화합물(2)의 디메틸포름아미드(25 ml) 현탁액에 3,5-디메틸-1-페닐-4-포르밀피라졸(1.41 g), 트리아세톡시수소화붕소나트륨(1.50 g) 및 초산(0.2 ml)을 첨가하고 실온에서 16시간 교반하였다. 반응 용액으로부터 수지를 여과하여 취하고, 디메틸포름아미드(20 ml×2회), 디클로로메탄(20 ml×2회), 메탄올(20 ml×2회) 및 디클로로메탄(20 ml×4회)으로 세정하여 화합물(3)을 얻었다.
참고예 6: 화합물(4)의 합성
참고예 5에서 제조한 화합물(3)을 50% 트리플루오로초산-디클로로메탄(25ml) 용액에 현탁하여 실온에서 5분간 교반하였다. 반응 용액을 여과하여 얻어진 수지를 재차 50% 트리플루오로초산-디클로로메탄 용액(25 ml)에 현탁하고, 실온에서 30분간 교반하였다. 반응 용액으로부터 여과하여 취한 수지를 디클로로메탄(25 ml×4회), 톨루엔(25 ml×4회), 1.25 M 초산-톨루엔 용액(25 ml×1회)으로 세정하여 화합물(4)을 얻었다.
참고예 7: 수지(5)의 합성
9-플루오레닐메틸옥시카르보닐아미노-Rink수지(수지(4))(5.0 g)(1% 디비닐벤젠 공중합체, 와타나베카가꾸사에서 제조, 카탈로그 번호 AO0102)를 디메틸포름아미드(50 ml×3회), 20% 피페리딘-디메틸포름아미드 용액 (50 ml×2회)으로 세정하였다. 세정한 수지를 20% 피페리딘-디메틸포름아미드 용액(50 ml)에 현탁하여 실온에서 30분간 교반하였다. 반응 용액을 여과하고, 얻어진 수지를 디메틸포름아미드(50 ml×5회)로 세정하였다. 세정한 수지의 디메틸포름아미드 (20 ml) 현탁액에 포름산에틸(30 ml)을 첨가하고 6시간 가열 환류하였다. 실온에서 냉각시킨 후, 반응 용액을 여과하였다. 여과하여 취한 수지를 디메틸포름아미드(50 ml×2회), 디클로로메탄(50 ml×4회), 메탄올(50 ml×4회) 및 디클로로메탄(50 ml×4회)으로 세정하고, 감압 건조하여 수지(5)(4.34 g)를 얻었다.
IR(KBr): ν 1693 cm-1.
참고예 8: 수지(6)의 합성
참고예 7에서 제조한 수지(4)(4.0 g)를 이용하여 참고예 2와 동일한 조작을 하여 수지(6)(3.56 g)를 얻었다.
IR(KBr): ν 2136 cm-1.
참고예 9: 화합물(5)의 합성
참고예 8에서 제조한 수지(6)(1.0 g), N-(6-페닐헥실)-4-피페리돈(0.44 g), n-프로필아민(0.14 ml) 및 N-(t-부틸옥시카르보닐)-L-류신(0.42 g)을 이용하여 참고예 3과 동일한 조작을 하여 화합물(5)을 얻었다.
참고예 10: 화합물(6)의 합성
참고예 9에서 제조한 화합물(5)의 1.5 M 2,6-루티딘-디클로로메탄(4 ml) 현탁액에 1 M 트리플루오로메탄설폰산트리메틸실릴-디클로로메탄 용액(4 ml)을 첨가하고 실온에서 30분간 교반하였다. 반응 용액을 여과하고, 얻어진 수지를 재차 1.5 M 2,6-루티딘-디클로로메탄 용액(4 ml)에 현탁하고, 1 M 트리플루오로메탄설폰산트리메틸실릴-디클로로메탄 용액(4 ml)을 첨가하고 실온에서 30분간 교반하였다. 반응 용액으로부터 수지를 여과하여 취하고, 디클로로메탄(6 ml×4회), 메탄올(6 ml×4회) 및 톨루엔(6 ml×5회)으로 세정하여 화합물(6)을 얻었다.
실시예 1
9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-2,5-디옥소-3-(2-메틸-1-프로필)-1-프로필-1,4,9-트리아자스피로[5.5]운데칸·2염산염
참고예 6에서 제조한 화합물(4)을 1.25 M 초산-톨루엔 용액(25 ml)에 현탁하여 90℃에서 24시간, 계속해서 실온에서 16시간 교반하였다. 반응 용액을 여과하고, 얻어진 수지를 클로로포름-메탄올(1:1; 20 ml×2회)로 세정하였다. 여과액과 세정액을 농축하였다. 잔류물을 실리카겔 칼럼 크로마토그래피(후지실리시아카가꾸사에서 제조, FL60D; 클로로포름:메탄올=30:1)로 정제하였다. 얻어진 잔류물의 메탄올 용액을 1N 염산에 의해 산성으로 한 후, 농축하여 이하의 물성치를 갖는 표제 화합물(703 mg)을 얻었다.
TLC: Rf 0.50(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.68-7.50(m, 5H), 4.36(s, 2H), 4.03(dd, J=7.8, 5.2Hz, 1H), 3.83(m, 2H), 3.64(m, 2H), 3.47(m, 2H), 2.64(m, 2H), 2.49(s, 3H), 2.44(s, 3H), 2.20(m, 2H), 1.81(m, 1H), 1.68(m, 2H), 1.60(m, 2H), 1.05-0.90(m, 9H);
IR(KBr): ν 3424, 3215, 2960, 2873, 2492, 1671, 1645, 1554, 1501, 1468, 1418, 1370, 1330, 1297, 1243, 1148, 958, 928, 754, 698 cm-1;
MS(MALDI, Pos., α-CHCA): 488(M+Na)+, 466(M+H)+, 185.
원소 분석: 계산치(C27H39N5O2·2HCl) C: 60.22%, H: 7.67%, N: 13.00%.
실측치 C: 59.89%, H: 7.67%, N: 12.79%.
실시예 2(1)∼2(3)
참고예 2에서 제조한 수지(3) 및 N-알릴옥시카르보닐-4-피페리돈을 이용하여 n-프로필아민 및 N-(t-부틸옥시카르보닐)류신 대신에 각각 해당하는 화합물을 이용하여 참고예 3→참고예 4와 동일한 조작을 하고, 또한, 3,5-디메틸-1-페닐-4-포르밀피라졸 대신에 해당하는 화합물을 이용하여 참고예 5→참고예 6→실시예 1과 동일한 조작을 하여 이하의 본 발명 화합물을 얻었다.
실시예 2(1)
9-(1,4-벤조디옥산-6-일메틸)-1-부틸-3-시클로헥실메틸-2,5-디옥소-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.63(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.08(d, J=2.2Hz, 1H), 6.99(dd, J=8.0, 2.2Hz, 1H), 6.92(d, J=8.0Hz, 1H), 4.27(s, 4H), 4.23(s, 2H), 4.04(dd, J=7.6, 4.8Hz, 1H), 3.74(m, 2H), 3.60-3.35(m, 4H), 2.43(m, 2H), 2.15(m, 2H), 1.90-1.60(m, 7H),1.60-1.45(m, 2H), 1.45-1.30(m, 2H), 1.30-1.10(m, 4H), 1.10-0.80(m, 5 H);
IR(KBr): ν 3436, 2926, 2852, 2511, 1675, 1645, 1591, 1511, 1418, 1374, 1294, 1261, 1068, 1050, 930, 888 cm-1;
MS(MALDI, Pos., α-CHCA): 484(M+H)+, 149.
원소 분석: 계산치(C28H41N3O4·HCl) C: 64.66%, H: 8.14%, N: 8.08%.
실측치 C: 64.00%, H: 7.94%, N: 7.90%.
실시예 2(2)
1-부틸-3-시클로헥실메틸-2,5-디옥소-9-(2-페닐이미다졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.25(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.05-7.94(m, 3H), 7.75-7.60(m, 3H), 4.59(s, 2H), 4.05(dd, J=7.4, 4.8Hz, 1H), 3.88(m, 2H), 3.65(m, 2H), 3.51(m, 2H), 2.68(m, 2H), 2.19(m, 2H), 1.90-1.60(m, 6H), 1.60-1.45(m, 3H), 1.45-1.30(m, 3H), 1.30-1.10(m, 3H), 1.10-0.80(m, 5H);
IR(KBr): ν 3423, 2927, 2854, 2664, 1672, 1644, 1421, 1373, 1177, 775, 709, 688 cm-1;
MS(MALDI, Pos., α-CHCA): 492(M+H)+.
원소 분석: 계산치(C29H41N5O2·2HCl·2.8H2O) C: 56.63%, H: 7.96%, N: 11.39%.
실측치 C: 56.90%, H: 7.23%, N: 10.78%.
실시예 2(3)
1-부틸-3-(2-메틸-1-프로필)-2,5-디옥소-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.63(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.54(d, J=8.8Hz, 2H), 7.40(m, 2H), 7.18(m, 1H), 7.11-7.00(m, 4H), 4.33(s, 2H), 4.01(dd, J=7.6, 4.8Hz, 1H), 3.80(m, 2H), 3.60-3.35(m, 4H), 2.46(m, 2H), 2.18(m, 2H), 1.80(m, 1H), 1.70(m, 1H), 1.54(m, 2H), 1.37(m, 3H), 1.00-0.90(m, 9H);
IR(KBr): ν 3440, 3221, 3066, 2957, 2871, 2559, 1673, 1590, 1509, 1489, 1419, 1371, 1329, 1242, 1172, 873, 693 cm-1;
MS(MALDI, Pos., α-CHCA): 478(M+H)+, 183.
원소 분석: 계산치(C29H39N3O3·HCl) C: 67.75%, H: 7.84%, N: 8.17%.
실측치 C: 67.29%, H: 7.70%, N: 8.06%.
실시예 2(4)
(3S)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1-프로필-1,4,9-트리아자스피로[5.5]운데칸·염산염
참고예 10에서 제조한 화합물(6)을 이용하여 실시예 1과 동일한 조작을 하여 이하의 물성치를 갖는 표제 화합물(69 mg)을 얻었다.
TLC: Rf 0.46(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.18(m, 5H), 4.02(dd, J=7.6, 4.8Hz, 1H), 3.70(m, 2H), 3.56(m, 2H), 3.39(m, 2H), 3.11(m, 2H), 2.63(dd, J=7.8, 7.2Hz, 2H), 2.48(m, 2H), 2.17(m, 2H), 1.95-1.50(m, 9H), 1.42(m, 4H), 1.00-0.89(m, 9H);
IR(KBr): ν 3435, 3205, 3082, 3026, 2935, 2870, 2493, 2361, 1674, 1454,1417, 1370, 1331, 1155, 1071, 1004, 961, 750, 700 cm-1;
MS(FAB, Pos., 글리세린-m-니트로벤질알콜): 442(M+H)+, 232, 171, 79(기준 피크).
원소 분석: 계산치(C27H43N3O2·HCl) C: 67.83%, H: 9.28%, N: 8.79%.
실측치 C: 67.56%, H: 9.50%, N: 8.71%.
실시예 2(5)
(3R)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1-프로필-1,4,9-트리아자스피로[5.5]운데칸·염산염
참고예 8에서 제조한 수지(6)(1.0 g), N-(6-페닐헥실)-4-피페리돈(0.44 g), n-프로필아민(0.14 ml) 및 N-(t-부틸옥시카르보닐)-D-류신(0.42 g)을 이용하여 참고예 9→참고예 10→실시예 1과 동일한 조작을 하여 이하의 물성치를 갖는 표제 화합물(63 mg)을 얻었다.
TLC: Rf 0.46(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.18(m, 5H), 4.02(dd, J=7.6, 4.6Hz, 1H), 3.70(m, 2H), 3.56(m, 2H), 3.39(m, 2H), 3.11(m, 2H), 2.63(dd, J=7.8, 7.2Hz, 2H), 2.48(m,2H), 2.17(m, 2H), 1.95-1.50(m, 9H), 1.42(m, 4H), 1.00-0.89(m, 9H);
IR(KBr): ν 3441, 3204, 3082, 3026, 2935, 2870, 2660, 2499, 2413, 2361, 1674, 1455, 1417, 1370, 1330, 1267, 1205, 1154, 1070, 1003, 960, 928, 899, 750, 700 cm-1;
MS(FAB, Pos., 글리세린-m-니트로벤질알콜): 442(M+H)+(기준 피크), 294, 232, 202, 171, 79.
원소 분석: 계산치(C27H43N3O2·HCl) C: 67.83%, H: 9.28%, N:8.79%.
실측치 C: 67.52%, H: 9.51%, N: 8.70%.
참고예 3(1)∼3(4)
참고예 2에서 제조한 수지(3) 및 N-알릴옥시카르보닐-4-피페리돈을 이용하여 n-프로필아민 및 N-(t-부틸옥시카르보닐)류신 대신에 각각 해당하는 화합물을 이용하여 참고예 3→참고예 4와 동일한 조작을 하고, 또한 3,5-디메틸-1-페닐-4-포르밀피라졸 대신에 해당하는 화합물을 이용하여 참고예 5→참고예 6→실시예 1과 동일한 조작을 하여 이하의 본 발명 화합물을 얻었다.
실시예 3(1)
1-부틸-9-((3,5-디메틸-1-페닐)-4-피라졸릴)메틸)-2,5-디옥소-3-(2-메틸-1-프로필)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.52(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.70-7.48(m, 5H), 4.35(s, 2H), 4.03(dd, J=7.8, 4.8Hz, 1H), 3.83(m, 2H), 3.63(m, 2H), 3.51(m, 2H), 2.64(m, 2H), 2.48(s, 3H), 2.43(s, 3H), 2.20(m, 2H), 1.81(m, 2H), 1.71(m, 2H), 1.55(m, 2H), 1.50-1.35(m, 4H), 1.05-0.90(m, 6H).
실시예 3(2)
1-부틸-3-시클로헥실메틸-2,5-디옥소-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.73(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.74-7.56(m, 1H), 7.53(d, J=8.8Hz, 2H), 7.40(m, 2H),7.18(m, 1H), 7.10-7.00(m, 3H), 4.33(s, 2H), 4.04(dd, J=7.4, 4.8Hz, 1H), 3.80(m, 2H), 3.60-3.35(m, 4H), 2.43(m, 2H), 2.17(m, 2H), 1.90-1.60(m, 7H), 1.60-1.45(m, 2H), 1.45-1.30(m, 2H), 1.30-1.15(m, 4H), 1.10-0.80(m, 5H).
실시예 3(3)
9-(1,4-벤조디옥산-6-일메틸)-1-부틸-3-(2-메틸-1-프로필)-2,5-디옥소-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.53(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.08(d, J=2.2Hz, 1H), 7.01(dd, J=8.2, 2.2Hz, 1H), 6.93(d, J=8.2Hz, 1H), 4.27(s, 4H), 4.23(s, 2H), 4.01(dd, J=7.8, 4.8Hz, 1H), 3.72(m, 2H), 3.55-3.35(m, 4H), 2.43(m, 2H), 2.16(m, 2H), 1.80(m, 1H), 1.67(m, 2H), 1.55(m, 2H), 1.37(m, 2H), 1.00-0.90(m, 9H).
실시예 3(4)
9-(4-벤질옥시페닐메틸)-1-부틸-2,5-디옥소-3-(2-메틸-1-프로필)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.59(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.54-7.25(m, 7H), 7.10(m, 2H), 5.13(s, 2H), 4.27(s, 2H), 4.00(dd, J=8.2, 4.8Hz, 1H), 3.72(m, 2H), 3.55-3.35(m, 4H), 2.42(m, 2H), 2.16(m, 2H), 1.90-1.25(m, 7H), 1.00-0.90(m, 9H).
실시예 4
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸·염산염
참고예 2에서 제조한 수지(3), N-(6-페닐헥실)-4-피페리돈, n-부틸아민 및 N-(t-부틸옥시카르보닐)류신을 이용하여 참고예 3→참고예 6→실시예 1과 동일한조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.62(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.30-7.06(m, 5H), 4.02(dd, J=7.8, 4.8Hz, 1H), 3.70(m, 2H), 3.56(m, 2H), 3.43(m, 2H), 3.11(m, 2H), 2.63(t, J=7.8Hz, 2H), 2.46(m, 2H), 2.18(m, 2H), 1.95-1.50(m, 9H), 1.50-1.25(m, 6H), 0.97(m, 9H).
실시예 5(1)∼5(12)
N-(6-페닐헥실)-4-피페리돈, n-프로필아민 및 N-(t-부틸옥시카르보닐)-L-류신 대신에 각각 해당하는 화합물과 참고예 8에서 제조한 수지(6)를 이용하여 참고예 9→참고예 10→실시예 1과 동일한 조작을 하여 이하의 본 발명 화합물을 얻었다.
실시예 5(1)
(3S)-1-(2-메틸프로필)-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.52(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.33(m, 10H), 5.07(s, 2H), 4.12(m, 1H), 3.94(m, 1H),3.61(m, 5H), 3.39(m, 2H), 3.13(m, 4H), 2.31(m, 4H), 1.92(m, 3H), 1.51(m, 2H), 1.39(m, 2H), 0.93(t, J=6.4Hz, 6H).
실시예 5(2)
(3S)-1-프로필-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.41(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.33(m, 10H), 5.06(m, 2H), 4.07(m, 1H), 3.86(m, 1H), 3.76(m, 1H), 3.63(m, 2H), 3.37(m, 4H), 3.12(m, 4H), 2.43(m, 2H), 2.21(m, 2H), 1.86(m, 2H), 1.55(m, 4H), 1.37(m, 2H), 0.95(t, J=7.2Hz, 3H).
실시예 5(3)
(3R)-1-프로필-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.41(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.33(m, 10H), 5.06(s, 2H), 4.07(m, 1H), 3.86(m, 1H), 3.76(m, 1H), 3.63(m, 2H), 3.37(m, 4H), 3.12(m, 4H), 2.43(m, 2H), 2.21(m, 2H), 1.86(m, 2H), 1.55(m, 4H), 1.37(m, 2H), 0.95(t, J=7.2Hz, 3H).
실시예 5(4)
(3S)-1-프로필-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.43(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.33(m, 5H), 7.26(m, 5H), 5.05(s, 2H), 4.05(m, 1H),3.85-3.30(m, 6H), 3.12(m, 4H), 2.73(t, J=7.6Hz, 2H), 2.44(m, 2H), 2.13(m, 4H), 1.85(m, 2H), 1.54(m, 4H), 1.38(m, 2H), 0.94(t, J=7.2Hz, 3H).
실시예 5(5)
(3R)-1-프로필-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.43(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.33(m, 5H), 7.26(m, 5H), 5.05(s, 2H), 4.05(m, 1H), 3.85-3.30(m, 6H), 3.12(m, 4H), 2.73(t, J=7.2Hz, 2H), 2.44(m, 2H), 2.13(m, 4H), 1.85(m, 2H), 1.54(m, 4H), 1.38(m, 2H), 0.94(t, J=7.2Hz, 3H).
실시예 5(6)
(3S)-1-프로필-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.44(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.33(m, 5H), 7.22(m, 5H), 5.06(s, 2H), 4.05(m, 1H), 3.85-3.38(m, 6H), 3.12(m, 4H), 2.70(m, 2H), 2.40(m, 2H), 2.18(m, 2H), 1.74(m, 6H), 1.54(m, 4H), 1.38(m, 2H), 0.94(t, J=7.0Hz, 3H).
실시예 5(7)
(3R)-1-프로필-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.44(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.33(m, 5H), 7.22(m, 5H), 5.06(s, 2H), 4.05(m, 1H),3.85-3.38(m, 6H), 3.12(m, 4H), 2.70(m, 2H), 2.40(m, 2H), 2.18(m, 2H), 1.74(m, 6H), 1.54(m, 4H), 1.38(m, 2H), 0.94(t, J=7.0Hz, 3H).
실시예 5(8)
(3S)-1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.57(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.48(m, 5H), 7.23(m, 5H), 4.82(m, 2H), 4.31(s, 2H), 4.17(dd, J=8.0, 4.6Hz, 1H), 3.72(m, 2H), 3.40(m, 2H), 2.52(m, 2H), 2.08(m, 2H), 2.00-1.60(m, 3H), 0.98(d, J=6.0Hz, 6H).
실시예 5(9)
(3R)-1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.57(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.48(m, 5H), 7.23(m, 5H), 4.82(m, 2H), 4.31(s, 2H), 4.17(dd, J=8.0, 4.6Hz, 1H), 3.72(m, 2H), 3.40(m, 2H), 2.52(m, 2H), 2.08(m, 2H), 2.00-1.60(m, 3H), 0.98(d, J=6.0Hz, 6H).
실시예 5(10)
(3S)-1-프로필-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(2-(2-페닐-5-메틸옥사졸-4-일)에틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.45(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.01(m, 2H), 7.53(m, 3H), 7.34(m, 5H), 5.07(s, 2H),4.08(dd, J=5.4, 4.4Hz, 1H), 4.00-3.60(m, 4H), 3.47(m, 4H), 3.13(m, 4H), 2.56(m, 2H), 2.46(s, 3H), 2.25(m, 2H), 1.87(m, 2H), 1.75-1.25(m, 6H), 0.94(t, J=7.2Hz, 3H).
실시예 5(11)
(3S)-1-프로필-2,5-디옥소-3-(4-(N-(2-클로로페닐메틸)옥시카르보닐)아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.33(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.33(m, 9H), 5.17(s, 2H), 4.08(dd, J=5.2, 4.8Hz, 1H), 3.80(m, 2H), 3.65(m, 3H), 3.39(m, 3H), 3.14(m, 4H), 2.50(m, 2H), 2.22(m, 2H), 1.85(m, 2H), 1.70-1.20(m, 6H), 0.95(t, J=7.2Hz, 3H).
실시예 5(12)
(3S)-1-프로필-2,5-디옥소-3-[3-(3-(2,4,6-트리메틸페닐설포닐)구아니디노)프로필]-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.39(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.32(m, 5H), 7.05(s, 2H), 4.10(m, 1H), 3.88(m, 1H), 3.67(m, 3H), 3.40(m, 4H), 3.18(m, 4H), 2.66(s, 6H), 2.51(m, 2H), 2.31(s, 3H), 2.21(m, 2H), 1.82(m, 2H), 1.60(m, 4H), 0.96(t, J=7.2Hz, 3H).
실시예 6(1)∼6(32)
참고예 2에서 제조한 수지(3), N-알릴옥시카르보닐-4-피페리돈, 해당하는 아민 유도체 및 해당하는 아미노산 유도체를 이용하여 참고예 3→참고예 4와 동일한 조작을 하고, 또한 해당하는 알데히드 유도체를 이용하여 참고예 5→참고예 6→실시예 1과 동일한 조작을 하여 이하의 본 발명 화합물을 얻었다.
실시예 6(1)
1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.61(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.55(m, 2H), 7.40(m, 2H), 7.18(m, 1H), 7.05(m, 4H), 4.33(s, 2H), 4.01(dd, J=7.6, 4.8Hz, 1H), 3.79(m, 2H), 3.60-3.30(m, 4H), 2.46(m, 2H), 2.17(m, 2H), 1.95-1.40(m, 5H), 0.94(m, 9H).
실시예 6(2)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.63(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.47(d, J=8.8Hz, 2H), 7.03(d, J=8.8Hz, 2H), 4.29(s, 2H), 4.04(dd, J=7.6, 4.8Hz, 1H), 3.83(s, 3H), 3.74(m, 2H), 3.55-3.35(m, 4H),2.41(m, 2H), 2.15(m, 2H), 1.85-1.55(m, 7H), 1.55-1.42(m, 3H), 1.42-1.30(m, 3H), 1.30-1.10(m, 2H), 1.08-0.80(m, 5H).
실시예 6(3)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-알릴옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.57(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.46(d, J=8.4Hz, 2H), 7.04(d, J=8.4Hz, 2H), 6.06(m, 1H), 5.41(m, 1H), 5.28(m, 2H), 4.59(m, 2H), 4.28(s, 2H), 4.04(dd, J=7.2, 4.8Hz, 1H), 3.77(m, 2H), 3.55-3.35(m, 4H), 2.39(m, 2H), 2.16(m, 2H), 1.90-1.60(m, 7H), 1.60-1.45(m, 2H), 1.45-1.30(m, 2H), 1.30-1.10(m, 3H), 1.10-0.80(m, 5H).
실시예 6(4)
(3S)-1-프로필-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-2,5-디옥소-3-(2-메틸-1-프로필)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.50(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.65-7.45(m, 5H), 4.33(s, 2H), 4.03(dd, J=7.8, 5.2Hz, 1H), 3.85(m, 2H), 3.62(m, 2H), 3.44(m, 2H), 2.59(m, 2H), 2.43(s, 3H), 2.41(s, 3H), 2.20(m, 2H), 1.81(m, 1H), 1.71(m, 2H), 1.64(m, 2H), 1.00-0.90(m, 9H).
실시예 6(5)
(3R)-1-프로필-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-2,5-디옥소-3-(2-메틸-1-프로필)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.50(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.65-7.45(m, 5H), 4.33(s, 2H), 4.03(dd, J=7.8, 5.2Hz, 1H), 3.85(m, 2H), 3.62(m, 2H), 3.44(m, 2H), 2.59(m, 2H), 2.43(s, 3H), 2.41(s,3H), 2.20(m, 2H), 1.81(m, 1H), 1.71(m, 2H), 1.64(m, 2H), 1.00-0.90(m, 9H).
실시예 6(6)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-페닐메틸-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.54(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.64-7.44(m, 5H), 4.36(s, 2H), 4.01(dd, J=7.8, 4.8Hz, 1H), 3.77(m, 2H), 3.55-3.35(m, 4H), 2.60-2.30(m, 2H), 2.17(m, 2H), 1.95-1.75(m, 1H), 1.75-1.60(m, 2H), 1.60-1.45(m, 2H), 1.45-1.20(m, 2H), 1.10-0.80(m, 9H).
실시예 6(7)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-벤질옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸
TLC: Rf 0.41(클로로포름:메탄올=20:1);
NMR(CDCl3): δ 7.45-7.28(m, 5H), 6.31(m, 1H), 5.15(s, 2H), 4.14(m, 2H), 3.96(m, 1H), 3.63(m, 1H), 3.44(m, 1H), 3.26(m, 2H), 1.99-1.14(m, 11H), 1.02-0.88(m, 9H).
실시예 6(8)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-벤질옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸
TLC: Rf 0.46(클로로포름:메탄올=20:1);
NMR(CDCl3): δ 7.40-7.29(m, 5H), 5.98(m, 1H), 5.15(s, 2H), 4.14(m, 2H),4.00(m, 1H), 3.65(m, 1H), 3.43(m, 1H), 3.26(m, 2H), 2.03-1.81(m, 4H), 1.80-1.60(m, 5H), 1.60-1.10(m, 10H), 1.10-0.85(m, 5H).
실시예 6(9)
1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.66(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.50(d, J=8.4Hz, 2H), 7.45-7.12(m, 8H), 7.10-6.98(m, 4H), 4.82(m, 2H), 4.29(s, 2H), 4.18(dd, J=8.0, 4.6Hz, 1H), 3.73(m, 2H), 3.42(m, 2H), 2.65-2.30(m, 2H), 2.20-2.05(m, 2H), 2.00-1.60(m, 3H), 0.98(d, J=6.2Hz, 6H).
실시예 6(10)
1-부틸-2,5-디옥소-3-프로필-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.36(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.51(d, J=8.7Hz, 2H), 7.39(dd, J=8.7, 7.5Hz, 2H), 7.18(t, J=7.5Hz, 1H), 7.10-7.00(m, 4H), 4.33(s, 2H), 4.04(dd, J=5.7, 4.5Hz, 1H), 3.93-3.66(m, 2H), 3.55-3.31(m, 4H), 2.47-2.09(m, 4H), 1.92-1.68(m, 2H), 1.61-1.21(m, 6H), 1.01-0.90(m, 6H).
실시예 6(11)
1-부틸-2,5-디옥소-3-메톡시메틸-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.48(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.51(d, J=8.7Hz, 2H), 7.39(dd, J=8.7, 7.2Hz, 2H),7.17(t, J=7.2Hz, 1H), 7.09-6.99(m, 4H), 4.30(s, 2H), 4.07(t, J=3.0Hz, 1H), 3.91(m, 1H), 3.77(dd, J=9.0, 3.0Hz, 1H), 3.67(m, 1H), 3.58-3.39(m, 4H), 3.31(s, 3H), 3.26(m, 1H), 2.48-2.13(m, 4H), 1.65(m, 1H), 1.53-1.28(m, 3H), 0.95(t, J=7.5Hz, 3H).
실시예 6(12)
1-(1-메틸프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.43(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.46(d, J=8.4Hz, 2H), 7.38(dd, J=8.4, 7.5Hz, 2H), 7.16(t, J=7.5Hz, 1H), 7.08-6.99(m, 4H), 4.15(s, 2H), 3.91-3.82(m, 1H), 3.81-3.65(m, 1H), 3.64-3.44(m, 1H), 3.44-3.15(m, 3H), 2.42-2.00(m, 4H), 1.88-1.56(m, 5H), 1.46-1.37(m, 3H), 0.99-0.85(m, 9H).
실시예 6(13)
1-(2-메틸부틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.49(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.49(d, J=8.7Hz, 2H), 7.39(dd, J=8.7, 7.2Hz, 2H), 7.17(t, J=7.2Hz, 1H), 7.08-6.94(m, 4H), 4.27(s, 2H), 4.04(dd, J=8.4, 4.5Hz, 1H), 3.83-3.21(m, 6H), 2.45-2.12(m, 4H), 1.92-1.56(m, 4H), 1.42(m, 1H), 1.14(m, 1H), 1.00-0.83(m, 12H).
실시예 6(14)
1-(2-메틸프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.50(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.50(d, J=8.7Hz, 2H), 7.39(dd, J=8.7, 7.5Hz, 2H),7.17(t, J=7.5Hz, 1H), 7.13-7.04(m, 4H), 4.28(s, 2H), 4.04(dd, J=8.1, 4.2Hz, 1H), 3.81-3.54(m, 2H), 3.52-3.21(m, 4H), 2.46-2.11(m, 4H), 2.00-1.57(m, 4H), 0.94(d, J=6.3Hz, 6H), 0.90(d, J=6.3Hz, 3H), 0.90(d, J=6.3Hz, 3H).
실시예 6(15)
1-(2-디메틸아미노에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.87(클로로포름:메탄올:28% 암모니아수=80:10:1);
NMR(CD3OD): δ 7.60(d, J=8.7Hz, 2H), 7.39(dd, J=8.7, 7.5Hz, 2H), 7.17(t, J=7.5Hz, 1H), 7.07-6.99(m, 4H), 4.33(s, 2H), 4.07(dd, J=8.4, 4.8Hz, 1H), 3.99-3.63(m, 4H), 3.53-3.42(m, 2H), 3.32-3.21(m, 2H), 2.99(s, 3H), 2.96(s, 3H), 2.70-2.49(m, 2H), 2.30-2.10(m, 2H), 1.93-1.56(m, 3H), 0.94(d, J=6.6Hz, 6H).
실시예 6(16)
1-(2-메톡시에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.40(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.47(d, J=8.7Hz, 2H), 7.39(dd, J=8.7, 7.5Hz, 2H), 7.17(t, J=7.5Hz, 1H), 7.09-6.99(m, 4H), 4.25(s, 2H), 4.03(dd, J=7.8, 4.8Hz, 1H), 3.75-3.34(m, 8H), 3.31(s, 3H), 2.48-2.28(m, 2H), 2.25-2.06(m, 2H), 1.90-1.57(m, 3H), 0.94(d, J=6.3Hz, 3H), 0.93(d, J=6.3Hz, 3H).
실시예 6(17)
1-(2-메틸티오에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.43(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.48(d, J=8.7Hz, 2H), 7.39(dd, J=8.7, 7.8Hz, 2H),7.17(t, J=7.8Hz, 1H), 7.08-6.99(m, 4H), 4.25(s, 2H), 4.02(dd, J=7.8, 4.5Hz, 1H), 3.81-3.49(m, 4H), 3.48-3.33(m, 2H), 2.74-2.51(m, 2H), 2.39-2.10(m, 7H), 1.90-1.56(m, 3H), 0.94(d, J=6.6Hz, 3H), 0.93(d, J=6.6Hz, 3H).
실시예 6(18)
1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.55(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.40-7.15(m, 5H), 7.03(d, J=2.0Hz, 1H), 6.96(dd, J=8.2, 2.0Hz, 1H), 6.90(d, J=8.2Hz, 1H), 4.80(m, 2H), 4.25(s, 4H), 4.21-4.10(m, 3H), 3.80-3.55(m, 2H), 3.50-3.30(m, 2H), 2.60-2.25(m, 2H), 2.20-2.00(m, 2H), 2.00-1.60(m, 3H), 0.98(d, J=6.4Hz, 6H).
실시예 6(19)
1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-(4-벤질옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.53(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.50-7.15(m, 12H), 7.07(d, J=8.8Hz, 2H), 5.12(s, 2H), 4.81(m, 2H), 4.24(s, 2H), 4.17(dd, J=8.4, 4.8Hz, 1H), 3.70-3.55(m, 2H), 3.50-3.35(m, 2H), 2.60-2.25(m, 2H), 2.20-2.00(m, 2H), 2.00-1.60(m, 3H), 0.98(d, J=6.0Hz, 6H).
실시예 6(20)
1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.50(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.70-7.45(m, 5H), 7.40-7.15(m, 5H), 4.92(m, 2H), 4.29(s, 2H), 4.20(dd, J=8.4, 4.8Hz, 1H), 3.90-3.65(m, 2H), 3.65-3.45(m, 2H), 2.85-2.50(m, 2H), 2.44(s, 3H), 2.39(s, 3H), 2.20-2.00(m, 2H), 2.00-1.60(m, 3H), 1.00(d, J=5.4Hz, 6H).
실시예 6(21)
1-(3-메틸페닐메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.56(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.18(t, J=7.8Hz, 1H), 7.10-6.85(m, 6H), 4.77(m, 2H), 4.25(s, 4H), 4.19(m, 3H), 3.68(m, 2H), 3.40(m, 2H), 2.60-2.30(m, 2H), 2.29(s, 3H), 2.20-2.00(m, 2H), 2.00-1.60(m, 3H), 0.99(d, J=6.2Hz, 6H).
실시예 6(22)
1-(3-메틸페닐메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.59(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.70-7.45(m, 5H), 7.18(t, J=7.4Hz, 1H), 7.10-7.00(m, 3H), 4.88(s, 2H), 4.31(s, 2H), 4.20(dd, J=8.2, 4.8Hz, 1H), 3.76(m, 2H), 3.60(m, 2H), 2.90-2.50(m, 2H), 2.47(s, 3H), 2.41(s, 3H), 2.30(s, 3H), 2.10(m, 2H), 1.88(m, 1H), 1.85-1.65(m, 2H), 1.00(d, J=5.8Hz, 6H).
실시예 6(23)
1-(1-메틸부틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.49, 0.56(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.49(d, J=8.7Hz, 2H), 7.39(dd, J=8.7, 7.5Hz, 2H),7.17(t, J=7.5Hz, 1H), 7.08-6.99(m, 4H), 4.26(s, 2H), 3.97-3.79(m, 2H), 3.78-3.60(m, 1H), 3.54-3.33(m, 3H), 2.47-2.29(m, 2H), 2.2 6-2.03(m, 3H), 1.87-1.71(m, 1H), 1.70-1.53(m, 3H), 1.48-1.16(m, 5H), 1.02-0.90(m, 9H).
실시예 6(24)
1-(3-메틸부틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.54(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.51(d, J=8.7Hz, 2H), 7.39(dd, J=8.7, 7.5Hz, 2H), 7.18(t, J=7.5Hz, 1H), 7.10-7.00(m, 4H), 4.33(s, 2H), 4.00(dd, J=8.1, 4.8Hz, 1H), 3.90-3.71(m, 2H), 3.56-3.34(m, 4H), 2.46-2.29(m, 2H), 2.28-2.10(m, 2H), 1.90-1.56(m, 4H), 1.55-1.32(m, 2H), 1.04-0.85(m, 12H).
실시예 6(25)
1-(2-메톡시페닐메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((3,5-디메틸-1-페닐)-4-피라졸릴)메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.38(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.59-7.41(m, 5H), 7.26-7.17(m, 1H), 6.99-6.84(m, 3H), 4.74(brs, 2H), 4.27(s, 2H), 4.19(dd, J=8.4, 4.5Hz, 1H), 3.88(s, 3H), 3.90-3.68(m, 2H), 3.62-3.45(m, 2H), 2.60-2.14(m, 4H), 2.35(s, 3H), 2.33(s, 3H), 2.00-1.63(m, 3H), 0.99(d, J=6.3Hz, 6H).
실시예 6(26)
1-(3-메톡시페닐메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((3,5-디메틸-1-페닐)-4-피라졸릴)메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.33(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.65-7.48(m, 5H), 7.20(t, J=8.1Hz, 1H), 6.85-6.80(m,2H), 6.77(dd, J=7.8, 2.1Hz, 1H), 4.90(brs, 2H), 4.31(s, 2H), 4.20(dd, J=8.1, 4.8Hz, 1H), 3.84-3.65(m, 2H), 3.75(s, 3H), 3.65-3.48(m, 2H), 2.84-2.56(m, 2H), 2.47(s, 3H), 2.40(s, 3H), 2.19-2.03(m, 2H), 2.00-1.65(m, 3H), 0.99(d, J=6.3Hz, 6H).
실시예 6(27)
1-(2-메틸페닐메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.35(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.63-7.46(m, 5H), 7.18-7.06(m, 3H), 6.99-6.91(m, 1H), 4.81(brs, 2H), 4.29(s, 2H), 4.20(dd, J=8.4, 4.5Hz, 1H), 3.90-3.66(m, 2H), 3.63-3.57(m, 2H), 2.75-2.40(m, 2H), 2.44(s, 3H), 2.40(s, 3H), 2.38(s, 3H), 2.30-2.10(m, 2H), 2.00-1.65(m, 3H), 0.99(d, J=6.3Hz, 6H).
실시예 6(28)
1-(3-메틸페닐메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.48(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.53-7.46(m, 2H), 7.42-7.36(m, 2H), 7.22-7.14(m, 2H), 7.06-6.96(m, 7H), 4.85-4.65(m, 2H), 4.28(s, 2H), 4.18(dd, J=8.1, 4.5Hz, 1H), 3.80-3.62(m, 2H), 3.50-3.30(m, 2H), 2.58-2.25(m, 2H), 2.29(s, 3H), 2.18-2.04(m, 2H), 1.95-1.62(m, 3H), 0.98(d, J=6.3Hz, 6H).
실시예 6(29)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-에틸티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.62(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.17(d, J=3.6Hz, 1H), 6.85(d, J=3.6Hz, 1H), 4.53(s, 2H),4.04(dd, J=7.8, 4.5Hz, 1H), 3.88-3.72(m, 2H), 3.58-3.45(m, 2H), 3.43-3.33(m, 2H), 2.87(q, J=7.5Hz, 2H), 2.50-2.30(m, 2H), 2.30-2.08(m, 2H), 1.83-1.10(m, 17H), 1.31(t, J=7.5Hz, 3H), 1.05-0.85(m, 2H), 0.95(t, J=7.5Hz, 3H).
실시예 6(30)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-에틸푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.62(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 6.63(d, J=3.0Hz, 1H), 6.14(d, J=3.0Hz, 1H), 4.39(s, 2H), 4.04(dd, J=7.5, 4.5Hz, 1H), 3.90-3.70(m, 2H), 3.55-3.40(m, 2H), 3.40-3.35(m, 2H), 2.69(q, J=7.5Hz, 2H), 2.50-2.30(m, 2H), 2.30-2.10(m, 2H), 1.85-1.05(m, 17H), 1.25(t, J=7.5Hz, 3H), 1.05-0.85(m, 2H), 0.96(t, J=7.5Hz, 3H).
실시예 6(31)
(3S)-1-부틸-2,5-디옥소-3-((1R)-1-히드록시-2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.47(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.52(d, J=9.0Hz, 2H), 7.44-7.35(m, 2H), 7.18(t, J=7.5Hz, 1H), 7.10-7.00(m, 4H), 4.33(s, 2H), 4.16-4.00(m, 2H), 3.75-3.40(m, 5H), 3.26-3.09(m, 1H), 2.56-2.08(m, 4H), 1.82-1.60(m, 2H), 1.50-1.30(m, 3H), 1.05-0.89(m, 9H).
실시예 6(32)
(3R)-1-부틸-2,5-디옥소-3-((1S)-1-히드록시-2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.47(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.52(d, J=9.0Hz, 2H), 7.44-7.35(m, 2H), 7.18(t, J=7.5Hz, 1H), 7.10-7.00(m, 4H), 4.33(s, 2H), 4.16-4.00(m, 2H), 3.75-3.40(m, 5H), 3.26-3.09(m, 1H), 2.56-2.08(m, 4H), 1.82-1.60(m, 2H), 1.50-1.30(m, 3H), 1.05-0.89(m, 9H).
실시예 7
(3S)-1-프로필-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-알릴옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸
참고예 8에서 제조한 수지(6), N-알릴옥시카르보닐-4-피페리돈, n-프로필아민 및 N-(t-부틸옥시카르보닐)-N'-(벤질옥시카르보닐)-L-리진을 이용하여 참고예 9→참고예 10→실시예 1과 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.24(초산에틸:헥산=4:1);
NMR(CD3OD): δ 7.35(m, 5H), 6.40(m, 1H), 5.96 (ddt, J=17.2, 10.2, 5.6Hz, 1H), 5.34(m, 1H), 5.24(m, 1H), 5.12(s, 2H), 4.88(m, 1H), 4.62(m, 2H), 4.10(m, 2H), 4.00(m, 1H), 3.75(m, 1H), 3.36(m, 2H), 3.18(m, 3H), 1.94(m, 6H), 1.51(m, 6H), 0.90(t, J=7.2Hz, 3H).
실시예 8
(3S)-1-프로필-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-1,4,9-트리아자스피로[5.5]운데칸
실시예 7에서 제조한 화합물을 이용하여 참고예 4와 동일한 조작을 하고, 또한 양 이온 교환수지 및 실리카겔 칼럼 크로마토그래피에 의해 정제하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.56(클로로포름:메탄올:28% 암모니아수=20:5:1);
NMR(CD3OD): δ 7.40-7.20(m, 10H), 5.06(s, 2H), 4.03(t, J=5.0Hz, 1H), 3.55-3.18(m, 4H), 3.12(t, J=6.6Hz, 2H), 3.08-2.98(m, 2H), 2.20-1.70(m, 6H), 1.70-1.20(m, 6H), 0.93(t, J=7.2Hz, 3H).
실시예 8(1)
1-프로필-2,5-디옥소-3-(2-메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸
N-(t-부틸옥시카르보닐)-N'-(벤질옥시카르보닐)-L-리진 대신에 N-(t-부틸옥시카르보닐)류신을 이용하여 실시예 7→실시예 8과 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.44(클로로포름:메탄올:트리에틸아민=18:2:1);
NMR(CD3OD): δ 3.99(d, J=7.8, 4.4Hz, 1H), 3.50-3.20(m, 4H), 3.05-2.85(m, 2H), 2.10-1.75(m, 5H), 1.75-1.40(m, 4H), 1.00-0.85(m, 9H).
실시예 9
1-부틸-2,5-디옥소-3-(2-메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸
실시예 6(7)에서 제조한 화합물(202 mg)의 메탄올(5 ml) 용액에 5% 팔라듐-탄소(20 mg)를 첨가하였다. 반응 혼합물을 수소 분위기하에 실온에서 3시간 교반하였다. 반응 혼합물을 세라이트(상품명)를 통해 여과하고, 여과액을 농축하여 이하의 물성치를 갖는 본 발명 화합물(127 mg)을 얻었다.
TLC: Rf 0.61(클로로포름:메탄올:28% 암모니아수=20:5:1);
NMR(CD3OD): δ 3.97(dd, J=7.8Hz, 4.5Hz, 1H), 3.48-3.22(m, 4H), 3.00-2.90(m, 2H), 2.12-1.60(m, 11H), 0.95(t, J=7.2Hz, 3H), 0.94(d, J=6.6Hz, 3H),0.93(d, J=6.6Hz, 3H).
실시예 9(1)
1-부틸-2,5-디옥소-3-시클로헥실메틸-1,4,9-트리아자스피로[5.5]운데칸
실시예 6(7)에서 제조한 화합물 대신에 실시예 6(8)에서 제조한 화합물을 이용하여 실시예 9와 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.65(클로로포름:메탄올:28% 암모니아수=20:5:1);
NMR(CD3OD): δ 4.00(dd, J=7.8Hz, 4.5Hz, 1H), 3.46-3.24(m, 4H), 3.03-2.92(m, 2H), 2.08-1.08(m, 19H), 1.05-0.84(m, 5H).
실시예 10
(3S)-1-프로필-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(4-디히드록시보란페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
실시예 8에서 제조한 화합물(70 mg)을 1% 초산의 디메틸포름아미드 용액(2 ml)에 용해하였다. 이 용액에 수소화트리아세톡시붕소나트륨(46 mg)과 4-포르밀페닐붕소산(30 mg)을 첨가하였다. 반응 혼합물을 실온에서 46시간 교반하였다. 반응 혼합물에 10% 초산의 메탄올 용액을 첨가하였다. 이 용액을 양이온 교환수지(본드에루트-SCX, 바리안사, 0.6 mmol/g, 500 mg/3 ml)에 통과시켜, 메탄올로 세정하였다. 또한, 10% 트리에틸아민의 메탄올 용액으로 용출하였다. 이 10% 트리에틸아민의 메탄올 용액으로 용출한 용액만을 농축하였다. 얻어진 잔류물을 실리카겔 칼럼 크로마토그래피(클로로포름:메탄올=1:0→30:1→10:1)에 의해 정제하여 이하의 물성치를 갖는 본 발명 화합물(45 mg)을 얻었다.
TLC: Rf 0.24(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.73(br, 2H), 7.52(br, 2H), 7.32(m, 5H), 5.03(s, 2H), 4.36(s, 2H), 4.05(t, J=4.8Hz, 1H), 3.81(m, 2H), 3.46(m, 3H), 3.10(t, J=6.6Hz, 2H), 2.37(br, 2H), 2.22(br, 2H), 1.92-1.66(m, 2H), 1.60-1.28(m, 7H), 0.91(t, J=7.5Hz, 3H).
실시예 10(1)
(3S)-1-프로필-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(1,3-벤조디옥살란-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
4-포르밀페닐붕소산 대신에 2,3-(메틸렌디옥시)벤조알데히드를 이용하여 실시예 10과 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.25(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.32(m, 5H), 6.96(m, 3H), 6.05(s, 2H), 5.04(s, 2H), 4.33(s, 2H), 4.05(t, J=4.5Hz, 1H), 3.98-3.54(m, 2H), 3.53(m, 2H), 3.38(m, 3H), 3.11(t, J=6.6Hz, 2H), 2.37(br, 2H), 2.22(br, 2H), 1.98-1.76(m, 2H), 1.61-1.28(m, 5H), 0.92(t, J=7.2Hz, 3H).
실시예 11
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(1-(1,4-벤조디옥산-6-일)에틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
실시예 9에서 제조한 화합물(315 mg)의 디클로로메탄(5 ml) 용액에 아르곤 분위기하에 1,4-벤조디옥산-6-일메틸케톤(285 mg), 트리에틸아민(0.354 ml), 사염화티탄의 디클로로메탄 용액(1.0 M 용액, 0.63 ml)을 첨가하였다. 반응 혼합물을 실온에서 16시간 교반하였다. 반응 혼합물에 시아노수소화붕소나트륨(133 mg)의 메탄올(2 ml) 용액을 첨가하였다. 반응 혼합물을 실온에서 1시간 교반하였다. 반응 혼합물에 2N 수산화나트륨 수용액을 가하여, 초산에틸로 추출하였다. 추출물을 무수황산나트륨으로 건조하여 농축하였다. 얻어진 잔류물을 실리카겔 칼럼 크로마토그래피(후지실리시아카가꾸, BW235; 클로로포름:메탄올=50:1)에 의해 정제하였다. 얻어진 잔류물을 메탄올에 용해하고, 1N 염산 수용액에 의해 산성으로 하며, 농축하여 이하의 물성치를 갖는 본 발명 화합물(176 mg)을 얻었다.
TLC: Rf 0.46(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.04(d, J=2.1Hz, 1H), 6.98(dd, J=8.4, 2.1Hz, 1H), 6.92(d, J=8.4Hz, 1H), 4.40(q, J=6.9Hz, 1H), 4.26(s, 4H), 3.98(dd, J=8.1, 4.5Hz, 1H), 3.82-3.17(m, 6H), 2.55-2.04(m, 4H), 1.87-1.28(m, 10H), 1.04-0.85(m, 9H).
실시예 11(1)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(1-(4-페닐옥시페닐)에틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
1,4-벤조디옥산-6-일메틸케톤 대신에 4-페녹시아세토페논을 이용하여 실시예 11과 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.58, 0.62(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.51(d, J=8.7Hz, 2H), 7.39(dd, J=8.7, 7.5Hz, 2H), 7.17(t, J=7.5Hz, 1H), 7.09-7.01(m, 4H), 4.48(m, 1H), 3.98(dd, J=7.8, 4.8Hz, 1H), 3.80-3.17(m, 6H), 2.56-2.28(m, 2H), 2.28-2.03(m, 2H), 1.88-1.24(m, 7H), 1.76(d, J=6.9Hz, 3H), 1.04-0.86(m, 9H).
실시예 12
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(1-(1,4-벤조디옥산-6-일)에틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
실시예 9에서 제조한 화합물 대신에 실시예 9(1)에서 제조한 화합물을 이용하여 실시예 11과 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.50(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.02(d, J=1.8Hz, 1H), 6.96(dd, J=8.4, 1.8Hz, 1H), 6.92(d, J=8.4Hz, 1H), 4.39(m, 1H), 4.26(s, 4H), 4.01(dd, J=7.5, 4.5Hz, 1H), 3.80-3.20(m, 6H), 2.50-2.02(m, 4H), 1.82-1.13(m, 18H), 1.04-0.83(m, 5H).
실시예 13
(3S)-1-프로필-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-알릴-1,4,9-트리아자스피로[5.5]운데칸·염산염
실시예 7에서 제조한 화합물(225 mg)의 테트라히드로푸란(5 ml) 용액에 아르곤 분위기하에 실온에서 테트라키스트리페닐포스핀팔라듐(0)(51 mg)을 첨가하였다. 반응 혼합물을 실온에서 16시간 교반하였다. 반응 혼합물을 양이온 교환수지(본드 에루트-SCX, 바리안사, 0.6 mmol/g, 500 mg/3 ml)에 통과시켜 메탄올로 세정하였다. 또한, 10% 트리에틸아민의 메탄올 용액(20 ml)으로 용출하였다. 이 10% 트리에틸아민의 메탄올 용액으로 용출한 용액만을 농축하였다. 얻어진 잔류물을 실리카겔 칼럼 크로마토그래피(클로로포름:메탄올=20:1)에 의해 정제하여 이하의 물성치를 갖는 본 발명 화합물(122 mg)을 얻었다.
TLC: Rf 0.34(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.34(m, 5H), 6.00(m, 1H), 5.62(m, 1H), 5.61(m, 1H), 5.06(s, 2H), 4.07(t, J=5.2Hz, 1H), 3.77(m, 4H), 3.44(m, 4H), 3.12(t, J=6.6Hz, 2H), 2.39(m, 2H), 2.20(m, 2H), 1.84(m, 2H), 1.54(m, 4H), 1.37(m, 2H), 0.94(t, J=7.2Hz, 3H).
실시예 14
(3S)-1-프로필-2,5-디옥소-3-(4-아미노부틸)-9-페닐에틸-1,4,9-트리아자스피로[5.5]운데칸
실시예 6(7)에서 제조한 화합물 대신에 실시예 5(11)에서 제조한 화합물을 이용하여 실시예 9와 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.66(클로로포름:메탄올:28% 암모니아수=20:5:1);
NMR(CD3OD): δ 7.23(m, 5H), 4.05(t, J=5.2Hz, 1H), 3.42(m, 2H), 2.98(m, 3H), 2.81(m, 3H), 2.65(m, 4H), 2.16(m, 2H), 1.99(m, 1H), 1.89(m, 3H), 1.53(m, 3H), 1.48(m, 3H), 0.94(t, J=7.2Hz, 3H).
실시예 15
(3S)-1-프로필-2,5-디옥소-3-(4-(N-(4-페닐)페닐카르보닐)아미노부틸)-9-페닐에틸-1,4,9-트리아자스피로[5.5]운데칸·염산염
실시예 14에서 제조한 화합물(42 mg)의 디클로로에탄(2 ml) 용액에 디이소프로필에틸아민(35 μl)과 4-페닐벤조일클로라이드(33 mg)를 첨가하였다. 반응 혼합물을 실온에서 3시간 교반하였다. 반응 혼합물을 양이온 교환수지(본드 에루트-SCX, 바리안사, 0.6 mmol/g, 500 mg/3 ml)에 통과시켜 메탄올로 세정하였다. 또한, 10% 트리에틸아민의 메탄올 용액(20 ml)으로 용출하였다. 이 10% 트리에틸아민의 메탄올 용액으로 용출한 용액만을 농축하였다. 얻어진 잔류물을 실리카겔 칼럼 크로마토그래피(클로로포름:메탄올=10:0→10:1)에 의해 정제하였다. 얻어진 생성물에 4N 염산의 초산에틸 용액을 첨가하여 이하의 물성치를 갖는 본 발명 화합물(66 mg)을 얻었다.
TLC: Rf 0.50(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.89(d, J=8.1Hz, 2H), 7.72(d, J=8.1Hz, 2H), 7.65(d, J=7.2Hz, 2H), 7.45(t, J=7.2Hz, 2H), 7.39-7.26(m, 6H), 4.11(m, 1H), 3.86-3.71(m, 2H), 3.63-3.53(m, 2H), 3.45-3.30(m, 4H), 3.07(m, 2H), 2.42(br, 2H), 2.19(m, 2H), 1.99-1.78(m, 2H), 1.68-1.28(m, 7H), 0.86(t, J=7.5Hz, 3H).
실시예 16
요오드화 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-메틸-9-(1-(1,4-벤조디옥산-6-일)에틸)-1,4,-디아자-9-아조니아스피로[5.5]운데칸
실시예 2(1)에서 제조한 화합물(50 mg)의 클로로포름(2 ml) 용액에 1N 수산화나트륨(2 ml)을 첨가하였다. 반응 혼합물을 실온에서 10분간 교반하였다. 반응 혼합물의 수층을 제거하였다. 유기층을 물로 세정하고, 무수 황산마그네슘으로 건조시켜 농축하였다. 얻어진 잔류물의 아세톤(2 ml) 용액에 요오드화메틸(118 μl)을 첨가하였다. 반응 혼합물을 실온에서 18시간 교반하였다. 반응 혼합물을 농축하였다. 얻어진 잔류물을 디에틸에테르에 의해 고화시켜 이하의 물성치를 갖는 본 발명 화합물(58 mg)을 얻었다.
TLC: Rf 0.23(초산에틸:초산:물=8:1:1);
NMR(CD3OD): δ 7.10-6.90(m, 3H), 4.60+4.49(s+s, 2H), 4.29(s, 4H), 4.20-4.00(m, 3H), 3.70-3.35(m, 4H), 3.11+2.99(s+s, 3H), 2.80-2.30(m, 2H), 2.30-2.00(m, 2H), 1.90-1.10(m, 15H), 1.10-0.80(m, 5H).
실시예 17
(3S)-3-(4-(N-벤질옥시카르보닐)아미노부틸)-2,5-디옥소-9-(2-히드록시-2-페닐에틸)-1-프로필-1,4,9-트리아자스피로[5,5]운데칸
실시예 8에서 제조한 화합물(0.01 g)의 2-프로판올(0.4 ml) 용액에 스티렌옥사이드(10 μl)를 첨가하였다. 반응 혼합물을 4시간 환류하였다. 반응 혼합물을 실온까지 냉각시킨 후, 반응 혼합물을 미리 메탄올(3 mL)로 세정한 이온 교환수지(OASIS MCX, Waters, 60 mg)에 흡착시켰다. 메탄올(2 mL)로 세정한 후, 10% 트리에틸아민-메탄올 용액(2 mL)으로 용출하였다. 용출액을 감압 농축하여 이하의 물성치를 갖는 본 발명 화합물(13 mg)을 얻었다.
TLC: Rf 0.34(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.40-7.20(m, 10H), 5.06(s, 2H), 4.03(m, 1H), 3.40(m, 2H), 3.12(m, 2H), 3.10-2.60(m, 6H), 2.50(m, 1H), 2.40-2.00(m, 2H), 2.00-1.70(m, 4H), 1.70-1.20(m, 6H), 0.93(t, J=7.2Hz, 3H).
실시예 18
(3S)-3-(4-(N-벤질옥시카르보닐)아미노부틸)-2,5-디옥소-9-(2-옥소-2-페닐에틸)-1-프로필-1,4,9-트리아자스피로[5,5]운데칸
실시예 8에서 제조한 화합물(0.01 g)의 디메틸포름아미드(0.4 ml) 용액에 트리에틸아민(6 μl), 브롬화페나실(9 mg)을 첨가하였다. 반응 혼합물액을 실온에서 24시간 방치하였다. 반응 혼합물에 초산(0.4 ml)을 첨가하여 산성으로 하였다. 반응 혼합물을 미리 메탄올(6 mL)로 세정한 이온 교환수지(OASIS MCX, Waters, 120 mg)에 흡착시켰다. 메탄올(2 ml)로 세정한 후, 10% 트리에틸아민-메탄올 용액(4 ml)으로 용출하였다. 용출액을 감압 농축하여 이하의 물성치를 갖는 본 발명 화합물(12 mg)을 얻었다.
TLC: Rf 0.33(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.01(m, 2H), 7.54(m, 3H), 7.33(m, 5H), 5.05(s, 2H), 4.02(m, 1H), 4.00(s, 2H), 3.44(m, 2H), 3.12(t, J=6.6Hz, 2H), 2.95(m, 2H), 2.40-2.10(m, 2H), 2.00-1.70(m, 5H), 1.68-1.20(m, 7H), 0.94(t, J=7.2Hz, 3H).
실시예 19
(3S)-1-(2-메틸프로필)-2,5-디옥소-3-메틸-9-알릴옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸
참고예 8에서 제조한 수지(6)(300 mg)의 테트라히드로푸란(1.5 ml)과 메탄올(1.5 ml)의 현탁액에 실온에서 N-알릴옥시카르보닐-4-피페리돈(403 mg), 이소부틸아민(0.22 ml) 및 N-(t-부틸옥시카르보닐)-L-알라닌(381 mg)을 첨가하였다. 반응 혼합물을 65℃에서 20시간 교반하였다. 반응 용액을 실온에서 냉각시키고, 수지를 여과하여 취하였다. 얻어진 수지를 테트라히드로푸란(3 ml×4회) 및 염화메틸렌(3 ml×5회)으로 세정하고, 건조시켜 수지(384 mg)를 얻었다. 얻어진 수지(146 mg)의 1.5 M 2,6-루티딘-염화메틸렌(2 ml) 현탁액에 1 M 트리플루오로메탄설폰산트리메틸실릴-염화메틸렌 용액(2 ml)을 첨가하여 실온에서 30분 교반하였다. 반응 용액을 여과하여 염화메틸렌(2 ml×3회)으로 세정하였다. 얻어진 수지를 재차 1.5 M 2,6-루티딘-염화메틸렌 용액(2 ml)에 현탁하고, 1 M 트리플루오로메탄설폰산트리메틸실릴-염화메틸렌 용액(2 ml)을 첨가하여 실온에서 30분 교반하였다. 반응 용액으로부터 수지를 여과하여 취하고, 염화메틸렌(2 ml×4회), 메탄올(2 ml×4회) 및 염화메틸렌(2 ml×4회)으로 세정하고, 건조시켜 수지를 얻었다. 얻어진 수지를 1.25 M 초산-톨루엔 용액(2 ml)에 현탁하였다. 반응 혼합물을 90℃에서 20시간 교반하였다. 반응 혼합물을 여과하여 톨루엔(2 ml×3회) 및 메탄올(2 ml×4회)로 세정하였다. 여과액을 농축하여 이하의 물성치를 갖는 본 발명 화합물(19 mg)을 얻었다.
TLC: Rf 0.39(클로로포름:메탄올=10:1);
MS(ESI, Pos., 20 V): 388(M+H)+;
HPLC 조건: F;
HPLC 유지 시간: 3.40 분;
NMR(CD3OD): δ 5.98(ddt, J=15.8, 10.4, 5.4Hz, 1H), 5.30(m, 1H), 5.21(m, 1H), 4.59(m, 2H), 4.20-4.00(m, 3H), 3.85-3.60(m, 2H), 3.41(dd, J=14.2, 8.0Hz, 1H), 3.18(dd, J=14.2, 7.2Hz, 1H), 2.10-1.70(m, 5H), 1.43(d, J=6.8Hz, 3H), 0.89(t, J=6.2Hz, 6H).
실시예 19(1)
(3S)-1-(2-메틸프로필)-2,5-디옥소-3-메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸·초산염
참고예 8에서 제조한 수지(6)(200 mg), N-(2-페닐에틸)-4-피페리돈(252 mg), 이소부틸아민(0.123 ml) 및 N-(t-부틸옥시카르보닐)-L-알라닌(235 mg)을 이용하여 실시예 19와 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물(50 mg)을얻었다.
TLC: Rf 0.46(클로로포름:메탄올=10:1);
MS(ESI, Pos., 20 V): 358(M+H)+;
HPLC 조건: F;
HPLC 유지 시간: 3.14 분;
NMR(CD3OD): δ 7.40-7.20(m, 5H), 4.15(q, J=6.8Hz, 1H), 3.65(m, 1H), 3.55-3.35(m, 3H), 3.25-3.05(m, 3H), 3.05-2.90(m, 3H), 2.50-2.05(m, 4H), 1.98(s, 3H), 1.92(m, 1H), 1.43(d, J=6.8Hz, 3H), 0.92(t, J=6.4Hz, 6H).
실시예 19(2)
(3S)-1-(2-메틸프로필)-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸·초산염
참고예 8에서 제조한 수지(6)(200 mg), N-(2-페닐에틸)-4-피페리돈(252 mg), 이소부틸아민(0.123 ml) 및 N-(t-부틸옥시카르보닐)-N'-(벤질옥시카르보닐)-L-리진 472 mg)을 이용하여 실시예 19와 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물(71 mg)을 얻었다.
TLC: Rf 0.44(클로로포름:메탄올=10:1);
MS(ESI, Pos., 20 V):549(M+H)+;
HPLC 조건: F;
HPLC 유지 시간: 3.49 분;
NMR(CD3OD): δ 7.40-7.20(m, 10H), 5.06(s, 2H), 4.10(m, 1H), 3.67(m, 1H), 3.60-3.40(m, 3H), 3.28-3.05(m, 5H), 3.05-2.90(m, 3H), 2.50-2.10(m, 4H), 1.98(s, 3H), 2.05-1.70(m, 3H), 1.65-1.20(m, 4H), 0.92(t, J=6.2Hz, 6H).
실시예 19(3)
(3S)-1-(1-벤질피페리딘-4-일)-2,5-디옥소-3-메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸·2초산염
참고예 8에서 제조한 수지(6)(200 mg), N-(2-페닐에틸)-4-피페리돈(252 mg), 4-아미노-1-벤질피페리딘(0.253 ml) 및 N-(t-부틸옥시카르보닐)-L-알라닌(235 mg)을 이용하여 실시예 19와 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물(41 mg)을 얻었다.
TLC: Rf 0.10(클로로포름:메탄올=10:1);
MS(ESI, Pos., 20 V): 475(M+H)+;
HPLC 조건: F;
HPLC 유지 시간: 3.09 분;
NMR(CD3OD): δ 7.47(m, 5H), 7.40-7.20(m, 5H), 4.19(s, 2H), 4.00(q, J=6.8Hz, 1H), 3.80-3.53(m, 4H), 3.53-3,35(m, 4H), 3.30-3.15(m, 2H), 3.15-2.90(m, 3H), 2,55-2.30(m, 3H), 2.30-2.00(m, 2H), 1.98(s, 6H), 1.85-1.70(m, 3H), 1.42(d, J=7.0Hz, 3H).
실시예 19(4)
(3S)-1-(1-벤질피페리딘-4-일)-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸·2초산염
참고예 8에서 제조한 수지(6)(200 mg), N-(2-페닐에틸)-4-피페리돈(252 mg), 4-아미노-1-벤질피페리딘(0.253 ml) 및 N-(t-부틸옥시카르보닐)-N'-(벤질옥시카르보닐)-L-리진(472 mg)을 이용하여 실시예 19와 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물(33 mg)을 얻었다.
TLC: Rf 0.12(클로로포름:메탄올=10:1);
MS(ESI, Pos., 20 V): 666(M+H)+;
HPLC 조건: F;
HPLC 유지 시간: 3.36 분;
NMR(CD3OD): δ 7.46(m, 5H), 7.40-7.20(m, 10H), 5.03(s, 2H), 4.19(s, 2H), 3.99(m, 1H), 3.80-3.40(m, 6H), 3.30-2.85(m, 9H), 2.50-2.10(m, 6H), 1.98(s, 6H), 1.95-1.60(m, 4H), 1.60-1.40(m, 4H).
실시예 19(5)
(3S)-1-(2,2-디페닐프로필)-2,5-디옥소-3-메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸·초산염
참고예 8에서 제조한 수지(6)(200 mg), N-(2-페닐에틸)-4-피페리돈(252 mg), 2,2-디페닐프로필아민(307 mg) 및 N-(t-부틸옥시카르보닐)-L-알라닌(235 mg)을 이용하여 실시예 19와 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물(22 mg)을 얻었다.
TLC: Rf 0.42(클로로포름:메탄올=10:1);
MS(ESI, Pos., 20 V): 496(M+H)+;
HPLC 조건: F;
HPLC 유지 시간: 3.58 분;
NMR(CD3OD): δ 7.40-7.10(m, 15H), 4.79(m, 1H), 4.16(m, 1H), 3.93(m, 1H), 3.71(s, 2H), 3.23(m, 1H), 3.10-2.80(m, 5H), 1.98(s, 3H), 1.95-1.82(m, 2H), 1.70-1.15(m, 1H), 1.58(s, 3H), 1.49(d, J=6.8Hz, 3H), 0.70(m, 1H).
실시예 19(6)
(3S)-1-(2,2-디페닐프로필)-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸·초산염
참고예 8에서 제조한 수지(6)(200 mg), N-(2-페닐에틸)-4-피페리돈(252 mg), 2,2-디페닐프로필아민(307 mg) 및 N-(t-부틸옥시카르보닐)-N'-(벤질옥시카르보닐)-L-리진(472 mg)을 이용하여 실시예 19와 동일한 조작을 행하여 이하의 물성치를 갖는 본 발명 화합물(18 mg)을 얻었다.
MS(ESI, Pos., 20 V): 687(M+H)+;
HPLC 조건: F;
HPLC 유지 시간: 3.80 분;
TLC: Rf 0.46(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.40-7.00(m, 20H), 5.06(s, 2H), 4.16(m, 1H), 3.93(m, 1H), 3.70(s, 2H), 3.55(m, 1H), 3.30-3.10(m, 2H), 3.10-2.80(m, 6H), 1.98(s, 3H), 1.95-1.85(m, 2H), 1.80(s, 3H), 1.70-1.30(m, 8 H).
실시예 19(7)
(3S)-1-프로필-2,5-디옥소-3-(4-벤질옥시페닐메틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸·초산염
참고예 8에서 제조한 수지(6)(0.5 g), N-(2-페닐에틸)-4-피페리돈(0.32 g), n-프로필아민(0.13 ml) 및 N-(t-부틸옥시카르보닐)-O-벤질-L-티로신(0.58 g)을 이용하여 실시예 19와 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물(68mg)을 얻었다.
TLC: Rf 0.51(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.50-7.10(m, 10H), 7.06(d, J=8.8Hz, 2H), 6.92(d, J=8.8Hz, 2H), 5.07(s, 2H), 4.31(m, 1H), 3.68(m, 1H), 3.40(m, 1H), 3.28-3.13(m, 4H), 3.13-2.80(m, 6H), 2.30-2.00(m, 2H), 1.80-1.35(m, 4H), 0.91(t, J=7.2Hz, 3H).
실시예 19(H1-1)∼19(H13-62)
참고예 8에서 제조한 수지(6), 해당하는 4-피페리돈 유도체, 해당하는 아민 유도체 및 해당하는 아미노산 유도체를 이용하여 실시예 19와 동일한 조작을 하여 이하의 표 1A-1∼13A-9에 화합물명을 나타내고 표 1B-1∼13B-7에 구조식을 나타낸 본 발명 화합물을 얻었다. 또한, 이들의 본 발명 화합물의 물성치를 이하의 표 1C-1∼13C-3에 나타내었다.
본 명세서의 표 중,
X1은 R1의 결합 부위를 나타내고,
X2는 R2의 결합 부위를 나타내며,
X3은 R3의 결합 부위를 나타내고,
X4는 R4의 결합 부위를 나타내며,
X5는 R5의 결합 부위를 나타낸다.
예컨대, 실시예 19(H1-1)의 구조식은 이하와 같이 표시된다.
또한, 본 명세서의 표 중의 고속 액체 크로마토그래피(HPLC)의 측정 조건을 이하에 나타내었다.
조건 A
사용한 칼럼: YMC-Pack FL-ODS, 50×4.6 mmI.D., S-5um, 120A
사용한 유속: 1 mL/분
사용한 용매
A액: 0.1% 트리플루오로초산 수용액
B액: 메탄올
측정 개시 후 2분간은 A액과 B액의 혼합비를 90/10으로 고정하였다. 그 후 20분간 A액과 B액의 혼합비를 20/80으로 직선적으로 바꾸었다. 그 후 5분간 A액과 B액의 혼합비를 20/80으로 고정하였다. 그 후 1분간으로 A액과 B액의 혼합비를 90/10으로 직선적으로 바꾸었다.
조건 B
사용한 칼럼: YMC-Pack FL-ODS, 50×4.6 mmI.D., S-5um, 120A
사용한 유속: 1 mL/분
사용한 용매
A액: 0.1% 트리플루오로초산 수용액
B액: 메탄올
측정 개시 후 2분간은 A액과 B액의 혼합비를 80/20으로 고정하였다. 그 후 20분간 A액과 B액의 혼합비를 20/80으로 직선적으로 바꾸었다. 그 후 5분간 A액과 B액의 혼합비를 20/80으로 고정하였다. 그 후 1분간 A액과 B액의 혼합비를 80/20으로 직선적으로 바꾸었다.
조건 C
사용한 칼럼: YMC-Pack FL-ODS, 50× 4.6 mmI.D., S-5um, 120A
사용한 유속: 1 mL/분
사용한 용매
A액: 0.1% 트리플루오로초산 수용액
B액: 메탄올
측정 개시 후 1분간은 A액과 B액의 혼합비를 90/10으로 고정하였다. 그 후 16분간 A액과 B액의 혼합비를 10/90으로 직선적으로 바꾸었다. 그 후 1분간 A액과 B액의 혼합비를 10/90으로 고정하였다. 그 후 1분간 A액과 B액의 혼합비를 90/10으로 직선적으로 바꾸었다.
조건 D
사용한 칼럼: YMC-Pack FL-ODS, 50× 4.6 mmI.D., S-5um, 120A
사용한 유속: 1 mL/분
사용한 용매
A액: 0.1% 트리플루오로초산 수용액
B액: 메탄올
측정 개시시 A액과 B액의 혼합비를 90/10으로 하였다. 그 후 16분간 A액과 B액의 혼합비를 10/90으로 직선적으로 바꾸었다. 그 후 0.5분간 A액과 B액의 혼합비를 10/90으로 고정하였다. 그 후 0.5분간 A액과 B액의 혼합비를 90/10으로 직선적으로 바꾸었다.
조건 E
사용한 칼럼: YMC-Pack FL-ODS, 50× 4.6 mmI.D., S-5um, 120A
사용한 유속: 3 mL/분
사용한 용매
A액: 0.1% 트리플루오로초산 수용액
B액: 메탄올
측정 개시시 A액과 B액의 혼합비를 90/10으로 하였다. 그 후 5분간 A액과 B액의 혼합비를 10/90으로 직선적으로 바꾸었다. 그 후 0.5분간 A액과 B액의 혼합비를 10/90으로 고정하였다. 그 후 0.1분간 A액과 B액의 혼합비를 90/10으로 직선적으로 바꾸었다.
조건 F
사용한 칼럼: XterraTMMS C185um, 4.6×50 mm I.D.
사용한 유속: 3 mL/분
사용한 용매
A액: 0.1% 트리플루오로초산 수용액
B액: 0.1% 트리플루오로초산-아세토니트릴 용액
측정 개시 후 0.5분간은 A액과 B액의 혼합비를 95/5로 고정하였다. 그 후 2.5분간 A액과 B액의 혼합비를 0/100으로 직선적으로 바꾸었다. 그 후 0.5분간 A액과 B액의 혼합비를 0/100으로 고정하였다. 그 후 0.01분간 A액과 B액의 혼합비를 95/5로 직선적으로 바꾸었다.
[표 1A-1]
실시예 번호
화합물명
19(H1-1)1-(푸란-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-2)1-(푸란-2-일메틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-3)1-(푸란-2-일메틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-4)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-5)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-6)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-페닐메틸-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-7)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-8)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-벤질옥시메틸-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-9)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
[표 1A-2]
실시예 번호
화합물명
19(H1-10)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-11)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-12)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-13)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-벤질옥시메틸-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-14)1-벤질-2,5-디옥소-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-15)1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-16)1-벤질-2,5-디옥소-3-페닐메틸-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-17)1-벤질-2,5-디옥소-3-(인돌-3-일메틸)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-18)1-벤질-2,5-디옥소-3-벤질옥시메틸-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
[표 1A-3]
실시예 번호
화합물명
19(H1-19)1-벤질-2,5-디옥소-3-벤질옥시카르보닐메틸-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-20)1-벤질-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-21)1-(2,2-디페닐에틸)-2,5-디옥소-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-22)1-(2,2-디페닐에틸)-2,5-디옥소-3-(2-메틸프로필)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-23)1-(2,2-디페닐에틸)-2,5-디옥소-3-페닐메틸-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-24)1-(2,2-디페닐에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-25)1-(2,2-디페닐에틸)-2,5-디옥소-3-벤질옥시메틸-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-26)1-(2,2-디페닐에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-27)1-(2,2-디페닐에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
[표 1A-4]
실시예 번호
화합물명
19(H1-28)1-(2-페닐에틸)-2,5-디옥소-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-29)1-(2-페닐에틸)-2,5-디옥소-3-(2-메틸프로필)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-30)1-(2-페닐에틸)-2,5-디옥소-3-페닐메틸-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-31)1-(2-페닐에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-32)1-(2-페닐에틸)-2,5-디옥소-3-벤질옥시메틸-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-33)1-(2-페닐에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-34)1-(2-페닐에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-35)1-프로필-2,5-디옥소-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-36)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-37)1-프로필-2,5-디옥소-3-페닐메틸-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
[표 1A-5]
실시예 번호
화합물명
19(H1-38)1-프로필-2,5-디옥소-3-(인돌-3-일메틸)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-39)1-프로필-2,5-디옥소-3-벤질옥시메틸-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-40)1-프로필-2,5-디옥소-3-벤질옥시카르보닐메틸-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-41)1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-42)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-43)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-44)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-페닐메틸-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-45)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-46)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-벤질옥시메틸-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
[표 1A-6]
실시예 번호
화합물명
19(H1-47)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-48)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-49)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-50)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-(2-메틸프로필)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-51)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-페닐메틸-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-52)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-(인돌-3-일메틸)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-53)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-벤질옥시메틸-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
19(H1-54)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
[표 1A-7]
실시예 번호
화합물명
19(H1-55)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
[표 2A-1]
실시예 번호
화합물명
19(H2-1)1-(푸란-2-일메틸)-2,5-디옥소-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-2)1-(푸란-2-일메틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-3)1-(푸란-2-일메틸)-2,5-디옥소-3-벤질옥시메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-4)1-(푸란-2-일메틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-5)1-(푸란-2-일메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-6)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-7)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-8)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-페닐메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 2A-2]
실시예 번호
화합물명
19(H2-9)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-10)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-벤질옥시메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-11)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-12)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-13)1-(2-(인돌-3-일)에틸)-2,5-디옥소-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-14)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-15)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-페닐메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-16)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 2A-3]
실시예 번호
화합물명
19(H2-17)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-벤질옥시메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-18)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-19)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-20)1-벤질-2,5-디옥소-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-21)1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-22)1-벤질-2,5-디옥소-3-페닐메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-23)1-벤질-2,5-디옥소-3-(인돌-3-일메틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-24)1-벤질-2,5-디옥소-3-벤질옥시메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-25)1-벤질-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 2A-4]
실시예 번호
화합물명
19(H2-26)1-벤질-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-27)1-(2,2-디페닐에틸)-2,5-디옥소-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-28)1-(2,2-디페닐에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-29)1-(2,2-디페닐에틸)-2,5-디옥소-3-페닐메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-30)1-(2,2-디페닐에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-31)1-(2,2-디페닐에틸)-2,5-디옥소-3-벤질옥시메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-32)1-(2,2-디페닐에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-33)1-(2,2-디페닐에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-34)1-(2-페닐에틸)-2,5-디옥소-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 2A-5]
실시예 번호
화합물명
19(H2-35)1-(2-페닐에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-36)1-(2-페닐에틸)-2,5-디옥소-3-페닐메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-37)1-(2-페닐에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-38)1-(2-페닐에틸)-2,5-디옥소-3-벤질옥시메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-39)1-(2-페닐에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-40)1-(2-페닐에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-41)1-프로필-2,5-디옥소-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-42)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-43)1-프로필-2,5-디옥소-3-페닐메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 2A-6]
실시예 번호
화합물명
19(H2-44)1-프로필-2,5-디옥소-3-(인돌-3-일메틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-45)1-프로필-2,5-디옥소-3-벤질옥시메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-46)1-프로필-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-47)1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-48)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-49)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-50)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-페닐메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-51)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 2A-7]
실시예 번호
화합물명
19(H2-52)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-벤질옥시메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-53)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-54)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-55)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-56)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-57)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-페닐메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-58)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-(인돌-3-일메틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-59)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-벤질옥시메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 2A-8]
실시예 번호
화합물명
19(H2-60)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H2-61)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 3A-1]
실시예 번호
화합물명
19(H3-1)1-(푸란-2-일메틸)-2,5-디옥소-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-2)1-(푸란-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-3)1-(푸란-2-일메틸)-2,5-디옥소-3-벤질-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-4)1-(푸란-2-일메틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-5)1-(푸란-2-일메틸)-2,5-디옥소-3-벤질옥시메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-6)1-(푸란-2-일메틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-7)1-(푸란-2-일메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-8)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-9)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
[표 3A-2]
실시예 번호
화합물명
19(H3-10)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-페닐메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-11)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-12)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-벤질옥시메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-13)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-14)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-15)1-(2-(인돌-3-일)에틸)-2,5-디옥소-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-16)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-17)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-페닐메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
[표 3A-3]
실시예 번호
화합물명
19(H3-18)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-19)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-벤질옥시메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-20)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-21)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-22)1-벤질-2,5-디옥소-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-23)1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-24)1-벤질-2,5-디옥소-3-페닐메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-25)1-벤질-2,5-디옥소-3-(인돌-3-일메틸)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
[표 3A-4]
실시예 번호
화합물명
19(H3-26)1-벤질-2,5-디옥소-3-벤질옥시메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-27)1-벤질-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-28)1-벤질-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-29)1-(2,2-디페닐에틸)-2,5-디옥소-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-30)1-(2,2-디페닐에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-31)1-(2,2-디페닐에틸)-2,5-디옥소-3-페닐메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-32)1-(2,2-디페닐에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-33)1-(2,2-디페닐에틸)-2,5-디옥소-3-벤질옥시메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-34)1-(2,2-디페닐에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
[표 3A-5]
실시예 번호
화합물명
19(H3-35)1-(2,2-디페닐에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-36)1-(2-페닐에틸)-2,5-디옥소-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-37)1-(2-페닐에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-38)1-(2-페닐에틸)-2,5-디옥소-3-페닐메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-39)1-(2-페닐에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-40)1-(2-페닐에틸)-2,5-디옥소-3-벤질옥시메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-41)1-(2-페닐에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-42)1-(2-페닐에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-43)1-프로필-2,5-디옥소-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
[표 3A-6]
실시예 번호
화합물명
19(H3-44)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-45)1-프로필-2,5-디옥소-3-페닐메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-46)1-프로필-2,5-디옥소-3-(인돌-3-일메틸)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-47)1-프로필-2,5-디옥소-3-벤질옥시메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-48)1-프로필-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-49)1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-50)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-51)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-52)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-페닐메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
[표 3A-7]
실시예 번호
화합물명
19(H3-53)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-54)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-벤질옥시메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-55)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-56)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-57)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-58)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-(2-메틸프로필)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-59)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-페닐메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-60)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-(인돌-3-일메틸)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
[표 3A-8]
실시예 번호
화합물명
19(H3-61)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-벤질옥시메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-62)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
19(H3-63)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
[표 4A-1]
실시예 번호
화합물명
19(H4-1)1-(푸란-2-일메틸)-2,5-디옥소-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-2)1-(푸란-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-3)1-(푸란-2-일메틸)-2,5-디옥소-3-벤질-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-4)1-(푸란-2-일메틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-5)1-(푸란-2-일메틸)-2,5-디옥소-3-벤질옥시메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-6)1-(푸란-2-일메틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-7)1-(푸란-2-일메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-8)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-9)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 4A-2]
실시예 번호
화합물명
19(H4-10)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-페닐메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-11)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-12)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-벤질옥시메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-13)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-14)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-15)1-(2-(인돌-3-일)에틸)-2,5-디옥소-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-16)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-17)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-페닐메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 4A-3]
실시예 번호
화합물명
19(H4-18)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-19)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-벤질옥시메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-20)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-21)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-22)1-벤질-2,5-디옥소-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-23)1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-24)1-벤질-2,5-디옥소-3-페닐메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-25)1-벤질-2,5-디옥소-3-(인돌-3-일메틸)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-26)1-벤질-2,5-디옥소-3-벤질옥시메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 4A-4]
실시예 번호
화합물명
19(H4-27)1-벤질-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-28)1-벤질-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-29)1-(2,2-디페닐에틸)-2,5-디옥소-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-30)1-(2,2-디페닐에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-31)1-(2,2-디페닐에틸)-2,5-디옥소-3-페닐메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-32)1-(2,2-디페닐에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-33)1-(2,2-디페닐에틸)-2,5-디옥소-3-벤질옥시메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-34)1-(2,2-디페닐에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-35)1-(2,2-디페닐에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 4A-5]
실시예 번호
화합물명
19(H4-36)1-(2-페닐에틸)-2,5-디옥소-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-37)1-(2-페닐에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-38)1-(2-페닐에틸)-2,5-디옥소-3-페닐메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-39)1-(2-페닐에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-40)1-(2-페닐에틸)-2,5-디옥소-3-벤질옥시메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-41)1-(2-페닐에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-42)1-(2-페닐에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-43)1-프로필-2,5-디옥소-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-44)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 4A-6]
실시예 번호
화합물명
19(H4-45)1-프로필-2,5-디옥소-3-페닐메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-46)1-프로필-2,5-디옥소-3-(인돌-3-일메틸)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-47)1-프로필-2,5-디옥소-3-벤질옥시메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-48)1-프로필-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-49)1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-50)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-51)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-52)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-페닐메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-53)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 4A-7]
실시예 번호
화합물명
19(H4-54)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-벤질옥시메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-55)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-56)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-57)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-58)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-59)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-페닐메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-60)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-(인돌-3-일메틸)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-61)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-벤질옥시메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 4A-8]
실시예 번호
화합물명
19(H4-62)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H4-63)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 5A-1]
실시예 번호
화합물명
19(H5-1)1-(푸란-2-일메틸)-2,5-디옥소-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-2)1-(푸란-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-3)1-(푸란-2-일메틸)-2,5-디옥소-3-벤질-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-4)1-(푸란-2-일메틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-5)1-(푸란-2-일메틸)-2,5-디옥소-3-벤질옥시메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-6)1-(푸란-2-일메틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-7)1-(푸란-2-일메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-8)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-9)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
[표 5A-2]
실시예 번호
화합물명
19(H5-10)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-페닐메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-11)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-12)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-벤질옥시메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-13)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-14)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-15)1-(2-(인돌-3-일)에틸)-2,5-디옥소-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-16)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-17)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-페닐메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-18)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
[표 5A-3]
실시예 번호
화합물명
19(H5-19)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-벤질옥시메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-20)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-21)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-22)1-벤질-2,5-디옥소-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-23)1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-24)1-벤질-2,5-디옥소-3-페닐메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-25)1-벤질-2,5-디옥소-3-(인돌-3-일메틸)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-26)1-벤질-2,5-디옥소-3-벤질옥시메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-27)1-벤질-2,5-디옥소-3-벤질옥시카르보닐메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
[표 5A-4]
실시예 번호
화합물명
19(H5-28)1-벤질-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-29)1-(2,2-디페닐에틸)-2,5-디옥소-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-30)1-(2,2-디페닐에틸)-2,5-디옥소-3-(2-메틸프로필)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-31)1-(2,2-디페닐에틸)-2,5-디옥소-3-페닐메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-32)1-(2,2-디페닐에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-33)1-(2,2-디페닐에틸)-2,5-디옥소-3-벤질옥시메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-34)1-(2,2-디페닐에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-35)1-(2,2-디페닐에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-36)1-(2-페닐에틸)-2,5-디옥소-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
[표 5A-5]
실시예 번호
화합물명
19(H5-37)1-(2-페닐에틸)-2,5-디옥소-3-(2-메틸프로필)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-38)1-(2-페닐에틸)-2,5-디옥소-3-페닐메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-39)1-(2-페닐에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-40)1-(2-페닐에틸)-2,5-디옥소-3-벤질옥시메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-41)1-(2-페닐에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-42)1-(2-페닐에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-43)1-프로필-2,5-디옥소-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-44)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-45)1-프로필-2,5-디옥소-3-페닐메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
[표 5A-6]
실시예 번호
화합물명
19(H5-46)1-프로필-2,5-디옥소-3-(인돌-3-일메틸)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-47)1-프로필-2,5-디옥소-3-벤질옥시메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-48)1-프로필-2,5-디옥소-3-벤질옥시카르보닐메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-49)1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-50)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-51)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-52)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-페닐메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-53)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-54)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-벤질옥시메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
[표 5A-7]
실시예 번호
화합물명
19(H5-55)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-56)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-57)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-(2-메틸프로필)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-58)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-페닐메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-59)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-(인돌-3-일메틸)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-60)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-벤질옥시메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-61)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
19(H5-62)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-페닐-1,4,9-트리아자스피로[5.5]운데칸
[표 6A-1]
실시예 번호
화합물명
19(H6-1)1-(푸란-2-일메틸)-2,5-디옥소-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-2)1-(푸란-2-일메틸)-2,5-디옥소-3-벤질옥시메틸-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-3)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-4)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-5)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-페닐메틸-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-6)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-7)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-벤질옥시메틸-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-8)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 6A-2]
실시예 번호
화합물명
19(H6-9)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-10)1-(2-(인돌-3-일)에틸)-2,5-디옥소-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-11)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-12)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-페닐메틸-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-13)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-14)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-벤질옥시메틸-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-15)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-16)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 6A-3]
실시예 번호
화합물명
19(H6-17)1-벤질-2,5-디옥소-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-18)1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-19)1-벤질-2,5-디옥소-3-페닐메틸-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-20)1-벤질-2,5-디옥소-3-(인돌-3-일메틸)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-21)1-벤질-2,5-디옥소-3-벤질옥시메틸-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-22)1-벤질-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-23)1-벤질-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-24)1-(2,2-디페닐에틸)-2,5-디옥소-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-25)1-(2,2-디페닐에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 6A-4]
실시예 번호
화합물명
19(H6-26)1-(2,2-디페닐에틸)-2,5-디옥소-3-페닐메틸-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-27)1-(2,2-디페닐에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-28)1-(2,2-디페닐에틸)-2,5-디옥소-3-벤질옥시메틸-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-29)1-(2,2-디페닐에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-30)1-(2,2-디페닐에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-31)1-(2-페닐에틸)-2,5-디옥소-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-32)1-(2-페닐에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-33)1-(2-페닐에틸)-2,5-디옥소-3-페닐메틸-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 6A-5]
실시예 번호
화합물명
19(H6-34)1-(2-페닐에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-35)1-(2-페닐에틸)-2,5-디옥소-3-벤질옥시메틸-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-36)1-(2-페닐에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-37)1-(2-페닐에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-38)1-프로필-2,5-디옥소-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-39)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-40)1-프로필-2,5-디옥소-3-페닐메틸-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-41)1-프로필-2,5-디옥소-3-(인돌-3-일메틸)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-42)1-프로필-2,5-디옥소-3-벤질옥시메틸-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 6A-6]
실시예 번호
화합물명
19(H6-43)1-프로필-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-44)1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-45)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-46)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-47)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-페닐메틸-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-48)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-49)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-벤질옥시메틸-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-50)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-벤질옥시.카르보닐메틸-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 6A-7]
실시예 번호
화합물명
19(H6-51)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-52)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-53)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-54)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-페닐메틸-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-55)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-(인돌-3-일메틸)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-56)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-벤질옥시메틸-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-57)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H6-58)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 7A-1]
실시예 번호
화합물명
19(H7-1)1-(푸란-2-일메틸)-2,5-디옥소-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-2)1-(푸란-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-3)1-(푸란-2-일메틸)-2,5-디옥소-3-벤질-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-4)1-(푸란-2-일메틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-5)1-(푸란-2-일메틸)-2,5-디옥소-3-벤질옥시메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-6)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-7)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-8)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-페닐메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-9)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
[표 7A-2]
실시예 번호
화합물명
19(H7-10)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-벤질옥시메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-11)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-12)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-13)1-(2-(인돌-3-일)에틸)-2,5-디옥소-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-14)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-15)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-페닐메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-16)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-17)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-벤질옥시메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
[표 7A-3]
실시예 번호
화합물명
19(H7-18)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-19)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-20)1-벤질-2,5-디옥소-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-21)1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-22)1-벤질-2,5-디옥소-3-페닐메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-23)1-벤질-2,5-디옥소-3-(인돌-3-일메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-24)1-벤질-2,5-디옥소-3-벤질옥시메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-25)1-벤질-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-26)1-벤질-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
[표 7A-4]
실시예 번호
화합물명
19(H7-27)1-(2,2-디페닐에틸)-2,5-디옥소-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-28)1-(2,2-디페닐에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-29)1-(2,2-디페닐에틸)-2,5-디옥소-3-페닐메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-30)1-(2,2-디페닐에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-31)1-(2,2-디페닐에틸)-2,5-디옥소-3-벤질옥시메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-32)1-(2,2-디페닐에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-33)1-(2,2-디페닐에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-34)1-(2-페닐에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
[표 7A-5]
실시예 번호
화합물명
19(H7-35)1-(2-페닐에틸)-2,5-디옥소-3-페닐메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-36)1-(2-페닐에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-37)1-(2-페닐에틸)-2,5-디옥소-3-벤질옥시메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-38)1-(2-페닐에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-39)1-(2-페닐에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-40)1-프로필-2,5-디옥소-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-41)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-42)1-프로필-2,5-디옥소-3-페닐메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-43)1-프로필-2,5-디옥소-3-(인돌-3-일메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
[표 7A-6]
실시예 번호
화합물명
19(H7-44)1-프로필-2,5-디옥소-3-벤질옥시메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-45)1-프로필-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-46)1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-47)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-48)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-49)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-페닐메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-50)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-51)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-벤질옥시메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
[표 7A-7]
실시예 번호
화합물명
19(H7-52)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-53)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-54)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-55)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-56)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-페닐메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-57)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-(인돌-3-일메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-58)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-벤질옥시메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H7-59)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
[표 7A-8]
실시예 번호
화합물명
19(H7-60)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
[표 8A-1]
실시예 번호
화합물명
19(H8-1)1-(푸란-2-일메틸)-2,5-디옥소-3-벤질-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-2)1-(푸란-2-일메틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-3)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-4)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-5)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-페닐메틸-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-6)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-7)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-벤질옥시메틸-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-8)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-9)1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
[표 8A-2]
실시예 번호
화합물명
19(H8-10)1-(2-(인돌-3-일)에틸)-2,5-디옥소-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-11)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-12)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-페닐메틸-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-13)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-14)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-벤질옥시메틸-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-15)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-16)1-(2-(인돌-3-일)에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-17)1-벤질-2,5-디옥소-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-18)1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
[표 8A-3]
실시예 번호
화합물명
19(H8-19)1-벤질-2,5-디옥소-3-페닐메틸-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-20)1-벤질-2,5-디옥소-3-(인돌-3-일메틸)-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-21)1-벤질-2,5-디옥소-3-벤질옥시메틸-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-22)1-벤질-2,5-디옥소-3-벤질옥시카르보닐메틸-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-23)1-벤질-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-24)1-(2,2-디페닐에틸)-2,5-디옥소-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-25)1-(2,2-디페닐에틸)-2,5-디옥소-3-(2-메틸프로필)-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-26)1-(2,2-디페닐에틸)-2,5-디옥소-3-페닐메틸-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-27)1-(2,2-디페닐에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
[표 8A-4]
실시예 번호
화합물명
19(H8-28)1-(2,2-디페닐에틸)-2,5-디옥소-3-벤질옥시메틸-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-29)1-(2,2-디페닐에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-30)1-(2,2-디페닐에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-31)1-(2-페닐에틸)-2,5-디옥소-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-32)1-(2-페닐에틸)-2,5-디옥소-3-(2-메틸프로필)-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-33)1-(2-페닐에틸)-2,5-디옥소-3-페닐메틸-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-34)1-(2-페닐에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-35)1-(2-페닐에틸)-2,5-디옥소-3-벤질옥시메틸-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-36)1-(2-페닐에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
[표 8A-5]
실시예 번호
화합물명
19(H8-37)1-(2-페닐에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-38)1-프로필-2,5-디옥소-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-39)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-40)1-프로필-2,5-디옥소-3-페닐메틸-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-41)1-프로필-2,5-디옥소-3-(인돌-3-일메틸)-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-42)1-프로필-2,5-디옥소-3-벤질옥시메틸-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-43)1-프로필-2,5-디옥소-3-벤질옥시카르보닐메틸-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-44)1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-45)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
[표 8A-6]
실시예 번호
화합물명
19(H8-46)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-페닐메틸-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-47)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-(인돌-3-일메틸)-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-48)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-벤질옥시메틸-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-49)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-50)1-(2-(t-부틸옥시카르보닐)에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-51)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-52)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-(2-메틸프로필)-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-53)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-페닐메틸-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-54)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-(인돌-3-일메틸)-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
[표 8A-7]
실시예 번호
화합물명
19(H8-55)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-벤질옥시메틸-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-56)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-벤질옥시카르보닐메틸-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
19(H8-57)1-(1-벤질피롤리딘-3-일)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-메틸-1,4,9-트리아자스피로[5.5]운데칸
[표 9A-1]
실시예 번호
화합물명
19(H9-1)(3S)-1-시클로프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-2)(3S)-1-시클로부틸-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-3)(3S)-1-((1S,2S,5S)-6,6-디메틸비시클로[3.1.1]헵탄-2-일메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-4)(3S)-1-시클로펜틸-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-5)(3S)-1-시클로헥실-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-6)(3S)-1-(시클로헥실메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-7)(3S)-1-(2-(1-메틸피롤리딘-2-일)에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 9A-2]
실시예 번호
화합물명
19(H9-8)(3S)-1-((1-에틸피롤리딘-2-일)메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-9)(3S)-1-(인단-5-일)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-10)(3S)-1-시클로헵틸-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-11)(3S)-1-(티오펜-2-일메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-12)(3S)-1-(2-(모르폴린-4-일)에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-13)(3S)-1-(3-(모르폴린-4-일)프로필)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-14)(3S)-1-(2-(피리딘-2-일)에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 9A-3]
실시예 번호
화합물명
19(H9-15)(3S)-1-(피리딘-3-일메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-16)(3S)-1-(피리딘-4-일메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-17)(3S)-1-(1-(에톡시카르보닐)피페리딘-4-일)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-18)(3S)-1-(2-(피페리딘-1-일)에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-19)(3S)-1-(1-페닐에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-20)(3S)-1-(1-메틸에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-21)(3S)-1-(1,3-디메틸부틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 9A-4]
실시예 번호
화합물명
19(H9-22)(3S)-1-(1-메틸-3-페닐프로필)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-23)(3S)-1-(1-메틸프로필)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-24)(3S)-1-(1-메틸부틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-25)(3S)-1-((2-플루오로페닐)메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-26)(3S)-1-((2-메톡시페닐)메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-27)(3S)-1-((3-플루오로페닐)메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-28)(3S)-1-((3-메톡시페닐)메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 9A-5]
실시예 번호
화합물명
19(H9-29)(3S)-1-((4-플루오로페닐)메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-30)(3S)-1-((4-메톡시페닐)메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-31)(3S)-1-((4-메틸페닐)메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-32)(3S)-1-(2,2-디메틸프로필)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-33)(3S)-1-(2-페닐프로필)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-34)(3S)-1-(2-메틸프로필)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-35)(3S)-1-(2-메틸부틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 9A-6]
실시예 번호
화합물명
19(H9-36)(3S)-1-벤질-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-37)(3S)-1-(2-(N,N-디메틸아미노)에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-38)(3S)-1-(2-메톡시에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-39)(3S)-1-(2-프로피닐)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-40)(3S)-1-(2-프로페닐)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-41)(3S)-1-(3-히드록시프로필)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-42)(3S)-1-(3-메틸부틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 9A-7]
실시예 번호
화합물명
19(H9-43)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-44)(3S)-1-(3-(N,N-디메틸아미노)프로필)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-45)(3S)-1-(3-에톡시프로필)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-46)(3S)-1-(3-페닐프로필)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-47)(3S)-1-(4-페닐부틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-48)(3S)-1-펜틸-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-49)(3S)-1-(3-(이미다졸-1-일)프로필)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 9A-8]
실시예 번호
화합물명
19(H9-50)(3S)-1-부틸-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-51)(3S)-1-(2-(1-시클로헥세닐)에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-52)(3S)-1-(시클로프로필메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-53)(3S)-1-에틸-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-54)(3S)-1-(3-메톡시프로필)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-55)(3S)-1-(2-(피리딘-4-일)에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-56)(3S)-1-((3-클로로페닐)메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 9A-9]
실시예 번호
화합물명
19(H9-57)(3S)-1-(3-메틸티오프로필)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-58)(3S)-1-(2-(티오펜-2-일)에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-59)(3S)-1-(2-(1,1-디메틸에틸티오)에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-60)(3S)-1-((t-부톡시카르보닐)메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-61)(3S)-1-((5-메틸푸란-2-일)메틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H9-62)(3S)-1-(2-(피리딘-3-일)에틸)-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 10A-1]
실시예 번호
화합물명
19(H10-1)(3S)-1-시클로프로필-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-2)(3S)-1-시클로부틸-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-3)(3S)-1-((1S,2S,5S)-6,6-디메틸비시클로[3.1.1]헵탄-2-일메틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-4)(3S)-1-시클로펜틸-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-5)(3S)-1-시클로헥실-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-6)(3S)-1-(시클로헥실메틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-7)(3S)-1-시클로옥틸-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 10A-2]
실시예 번호
화합물명
19(H10-8)(3S)-1-(2-(1-메틸피롤리딘-2-일)에틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-9)(3S)-1-((1-에틸피롤리딘-2-일)메틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-10)(3S)-1-(인단-5-일)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-11)(3S)-1-시클로헵틸-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-12)(3S)-1-(티오펜-2-일메틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-13)(3S)-1-(2-(모르폴린-4-일)에틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-14)(3S)-1-(3-(모르폴린-4-일)프로필)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 10A-3]
실시예 번호
화합물명
19(H10-15)(3S)-1-(2-(피리딘-2-일)에틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-16)(3S)-1-(피리딘-3-일메틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-17)(3S)-1-(피리딘-4-일메틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-18)(3S)-1-(1-(에톡시카르보닐)피페리딘-4-일)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-19)(3S)-1-(2-(피페리딘-1-일)에틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-20)(3S)-1-페닐-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-21)(3S)-1-(1-페닐에틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 10A-4]
실시예 번호
화합물명
19(H10-22)(3S)-1-(1-메틸에틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-23)(3S)-1-(1,3-디메틸부틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-24)(3S)-1-(1-메틸-3-페닐프로필)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-25)(3S)-1-(1-메틸프로필)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-26)(3S)-1-(1-에틸프로필)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-27)(3S)-1-(1-메틸부틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-28)(3S)-1-((2-플루오로페닐)메틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 10A-5]
실시예 번호
화합물명
19(H10-29)(3S)-1-((2-메톡시페닐)메틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-30)(3S)-1-((3-플루오로페닐)메틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-31)(3S)-1-((3-메톡시페닐)메틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-32)(3S)-1-((4-플루오로페닐)메틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-33)(3S)-1-((4-메톡시페닐)메틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-34)(3S)-1-((4-메틸페닐)메틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-35)(3S)-1-(2,2-디메틸프로필)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 10A-6]
실시예 번호
화합물명
19(H10-36)(3S)-1-(2-페닐프로필)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-37)(3S)-1-(2-메틸프로필)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-38)(3S)-1-(2-메틸부틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-39)(3S)-1-벤질-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-40)(3S)-1-(2-(N,N-디메틸아미노)에틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-41)(3S)-1-(2-메톡시에틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-42)(3S)-1-(2-프로피닐)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 10A-7]
실시예 번호
화합물명
19(H10-43)(3S)-1-(2-프로페닐)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-44)(3S)-1-(3-히드록시프로필)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-45)(3S)-1-(3-메틸부틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-46)(3S)-1-프로필-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-47)(3S)-1-(3-(N,N-디메틸아미노)프로필)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-48)(3S)-1-(3-에톡시프로필)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-49)(3S)-1-(3-페닐프로필)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 10A-8]
실시예 번호
화합물명
19(H10-50)(3S)-1-(4-페닐부틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-51)(3S)-1-펜틸-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-52)(3S)-1-(3-(이미다졸-1-일)프로필)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-53)(3S)-1-부틸-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-54)(3S)-1-(2-(1-시클로헥세닐)에틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-55)(3S)-1-(시클로프로필메틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-56)(3S)-1-에틸-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 10A-9]
실시예 번호
화합물명
19(H10-57)(3S)-1-(3-메톡시프로필)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-58)(3S)-1-(2-(N-에틸-N-(3-메틸페닐)아미노)에틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-59)(3S)-1-(2-(피리딘-4-일)에틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-60)(3S)-1-((3-클로로페닐)메틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-61)(3S)-1-(3-메틸티오프로필)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-62)(3S)-1-(2-(티오펜-2-일)에틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-63)(3S)-1-(2-(1,1-디메틸에틸티오)에틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 10A-10]
실시예 번호
화합물명
19(H10-64)(3S)-1-((t-부톡시카르보닐)메틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-65)(3S)-1-((2 S)-2-히드록시프로필)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-66)(3S)-1-((5-메틸푸란-2-일)메틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-67)(3S)-1-((1R)-1-(4-메틸페닐)에틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H10-68)(3S)-1-(2-(피리딘-3-일)에틸)-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 11A-1]
실시예 번호
화합물명
19(H11-1)(3S)-1-시클로프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-2)(3S)-1-시클로부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-3)(3S)-1-((1S,2S,5S)-6,6-디메틸비시클로[3.1.1]헵탄-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-4)(3S)-1-시클로펜틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-5)(3S)-1-시클로헥실-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-6)(3S)-1-(시클로헥실메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-7)(3S)-1-(2-(1-메틸피롤리딘-2-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-8)(3S)-1-((1-에틸피롤리딘-2-일)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 11A-2]
실시예 번호
화합물명
19(H11-9)(3S)-1-(인단-5-일)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-10)(3S)-1-시클로헵틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-11)(3S)-1-(티오펜-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-12)(3S)-1-(2-(모르폴린-4-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-13)(3S)-1-(3-(모르폴린-4-일)프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-14)(3S)-1-(2-(피리딘-2-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-15)(3S)-1-(피리딘-3-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 11A-3]
실시예 번호
화합물명
19(H11-16)(3S)-1-(피리딘-4-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-17)(3S)-1-(1-(에톡시카르보닐)피페리딘-4-일)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-18)(3S)-1-(2-(피페리딘-1-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-19)(3S)-1-(1-페닐에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-20)(3S)-1-(1-메틸에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-21)(3S)-1-((2-플루오로페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-22)(3S)-1-((2-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 11A-4]
실시예 번호
화합물명
19(H11-23)(3S)-1-((3-플루오로페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-24)(3S)-1-((3-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-25)(3S)-1-((4-플루오로페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-26)(3S)-1-((4-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-27)(3S)-1-((4-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-28)(3S)-1-(2,2-디메틸프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-29)(3S)-1-(2-페닐프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 11A-5]
실시예 번호
화합물명
19(H11-30)(3S)-1-(2-메틸프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-31)(3S)-1-(2-메틸부틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-32)(3S)-1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-33)(3S)-1-(2-(N,N-디메틸아미노)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-34)(3S)-1-(2-메톡시에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-35)(3S)-1-(2-프로피닐)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-36)(3S)-1-(2-프로페닐)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-37)(3S)-1-(3-히드록시프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 11A-6]
실시예 번호
화합물명
19(H11-38)(3S)-1-(3-메틸부틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-39)(3S)-1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-40)(3S)-1-(3-(N,N-디메틸아미노)프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-41)(3S)-1-(3-에톡시프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-42)(3S)-1-(3-페닐프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-43)(3S)-1-(4-페닐부틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-44)(3S)-1-펜틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-45)(3S)-1-(3-(이미다졸-1-일)프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 11A-7]
실시예 번호
화합물명
19(H11-46)(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-47)(3S)-1-(2-(1-시클로헥세닐)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-48)(3S)-1-(시클로프로필메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-49)(3S)-1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-50)(3S)-1-(3-메톡시프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-51)(3S)-1-(2-(피리딘-4-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-52)(3S)-1-((3-클로로페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-53)(3S)-1-(3-메틸티오프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 11A-8]
실시예 번호
화합물명
19(H11-54)(3S)-1-(2-(티오펜-2-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-55)(3S)-1-(2-(1,1-디메틸에틸티오)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-56)(3S)-1-((t-부톡시카르보닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-57)(3S)-1-((5-메틸푸란-2-일)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H11-58)(3S)-1-(2-(피리딘-3-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 12A-1]
실시예 번호
화합물명
19(H12-1)(3S)-1-시클로프로필-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-2)(3S)-1-시클로부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-3)(3S)-1-((1S,2S,5S)-6,6-디메틸비시클로[3.1.1]헵탄-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-4)(3S)-1-시클로펜틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-5)(3S)-1-시클로헥실-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-6)(3S)-1-(시클로헥실메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-7)(3S)-1-(1,2,3,4-테트라히드로나프틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-8)(3S)-1-시클로옥틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 12A-2]
실시예 번호
화합물명
19(H12-9)(3S)-1-(2-(1-메틸피롤리딘-2-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-10)(3S)-1-((1-에틸피롤리딘-2-일)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-11)(3S)-1-(인단-5-일)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-12)(3S)-1-시클로헵틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-13)(3S)-1-(티오펜-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-14)(3S)-1-(2-(모르폴린-4-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-15)(3S)-1-(3-(모르폴린-4-일)프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 12A-3]
실시예 번호
화합물명
19(H12-16)(3S)-1-(2-(피리딘-2-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-17)(3S)-1-(피리딘-3-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-18)(3S)-1-(피리딘-4-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-19)(3S)-1-(2-(피페리딘-1-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-20)(3S)-1-페닐-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-21)(3S)-1-(1-페닐에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-22)(3S)-1-(1-메틸에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 12A-4]
실시예 번호
화합물명
19(H12-23)(3S)-1-(1,3-디메틸부틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-24)(3S)-1-(1-메틸-3-페닐프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-25)(3S)-1-(1-메틸프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-26)(3S)-1-(1-에틸프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-27)(3S)-1-(1-메틸부틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-28)(3S)-1-((2-플루오로페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-29)(3S)-1-((2-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 12A-5]
실시예 번호
화합물명
19(H12-30)(3S)-1-((3-플루오로페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-31)(3S)-1-((3-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-32)(3S)-1-((4-플루오로페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-33)(3S)-1-((4-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-34) (3S)-1-((4-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-35) (3S)-1-(2,2-디메틸프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-36)(3S)-1-(2-페닐프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 12A-6]
실시예 번호
화합물명
19(H12-37)(3S)-1-(2-메틸프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-38)(3S)-1-(2-메틸부틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-39)(3S)-1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-40)(3S)-1-(2-(N,N-디메틸아미노)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-41)(3S)-1-(2-메톡시에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-42)(3S)-1-(2-프로피닐)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-43)(3S)-1-(2-프로페닐)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-44) (3S)-1-(3-히드록시프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 12A-7]
실시예 번호
화합물명
19(H12-45)(3S)-1-(3-메틸부틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-46)(3S)-1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-47)(3S)-1-(3-(N,N-디메틸아미노)프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-48)(3S)-1-(3-에톡시프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-49)(3S)-1-(3-페닐프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-50)(3S)-1-(4-페닐부틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-51)(3S)-1-펜틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-52)(3S)-1-(3-(이미다졸-1-일)프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 12A-8]
실시예 번호
화합물명
19(H12-53)(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-54)(3S)-1-(2-(1-시클로헥세닐)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-55)(3S)-1-(시클로프로필메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-56)(3S)-1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-57)(3S)-1-(1-프로필부틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-58)(3S)-1-(3-메톡시프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-59)(3S)-1-(2-(피리딘-4-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-60)(3S)-1-((3-클로로페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 12A-9]
실시예 번호
화합물명
19(H12-61)(3S)-1-(3-메틸티오프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-62)(3S)-1-(2-(티오펜-2-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-63)(3S)-1-(2-(1,1-디메틸에틸티오)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-64)(3S)-1-((t-부톡시카르보닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-65)(3S)-1-((2R)-2-히드록시프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-66)(3S)-1-((2S)-2-히드록시프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-67)(3S)-1-((5-메틸푸란-2-일)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 12A-10]
실시예 번호
화합물명
19(H12-68)(3S)-1-((1R)-1-(4-메틸페닐)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
19(H12-69)(3S)-1-(2-(피리딘-3-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐펜틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 13A-1]
실시예 번호
화합물명
19(H13-1)(3S)-1-시클로프로필-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-2)(3S)-1-시클로부틸-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-3)(3S)-1-((1S,2S,5S)-6,6-디메틸비시클로[3.1.1]헵탄-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-4)(3S)-1-시클로펜틸-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-5)(3S)-1-시클로헥실-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-6)(3S)-1-(시클로헥실메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-7)(3S)-1-(1,2,3,4-테트라히드로나프틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-8)(3S)-1-시클로옥틸-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
[표 13A-2]
실시예 번호
화합물명
19(H13-9)(3S)-1-(2-(1-메틸피롤리딘-2-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-10)(3S)-1-((1-에틸피롤리딘-2-일)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-11)(3S)-1-(인단-5-일)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-12)(3S)-1-시클로헵틸-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-13)(3S)-1-(티오펜-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-14)(3S)-1-(2-(모르폴린-4-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-15)(3S)-1-(3-(모르폴린-4-일)프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
[표 13A-3]
실시예 번호
화합물명
19(H13-16)(3S)-1-(2-(피리딘-2-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-17)(3S)-1-(피리딘-3-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-18)(3S)-1-(1-(에톡시카르보닐)피페리딘-4-일)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-19)(3S)-1-(2-(피페리딘-1-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-20)(3S)-1-(1-페닐에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-21)(3S)-1-(1,2-디메틸프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-22)(3S)-1-(1,3-디메틸부틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
[표 13A-4]
실시예 번호
화합물명
19(H13-23)(3S)-1-(1-에틸프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-24)(3S)-1-((2-플루오로페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-25)(3S)-1-((2-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-26)(3S)-1-((3-플루오로페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-27)(3S)-1-((3-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-28)(3S)-1-((4-플루오로페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-29)(3S)-1-((4-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
[표 13A-5]
실시예 번호
화합물명
19(H13-30)(3S)-1-((4-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-31)(3S)-1-(2,2-디메틸프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-32)(3S)-1-(2-페닐프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-33)(3S)-1-(2-메틸프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-34)(3S)-1-(2-메틸부틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-35)(3S)-1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-36)(3S)-1-(2-(N,N-디메틸아미노)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-37)(3S)-1-(2-메톡시에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
[표 13A-6]
실시예 번호
화합물명
19(H13-38)(3S)-1-(2-프로피닐)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-39)(3S)-1-(2-프로페닐)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-40) (3S)-1-(3-히드록시프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-41)(3S)-1-(3-메틸부틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-42)(3S)-1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-43)(3S)-1-(3-(N,N-디메틸아미노)프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-44)(3S)-1-(3-에톡시프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-45)(3S)-1-(3-페닐프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
[표 13A-7]
실시예 번호
화합물명
19(H13-46)(3S)-1-(4-페닐부틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-47)(3S)-1-펜틸-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-48)(3S)-1-(3-(이미다졸-1-일)프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-49)(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-50)(3S)-1-(2-(1-시클로헥세닐)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-51)(3S)-1-(시클로프로필메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-52)(3S)-1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-53)(3S)-1-(1-프로필부틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
[표 13A-8]
실시예 번호
화합물명
19(H13-54)(3S)-1-(3-메톡시프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-55)(3S)-1-(2-(피리딘-4-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-56)(3S)-1-((3-클로로페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-57) (3S)-1-(3-메틸티오프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-58)(3S)-1-(2-(티오펜-2-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-59)(3S)-1-(2-(1,1-디메틸에틸티오)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-60)(3S)-1-((t-부톡시카르보닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
[표 13A-9]
실시예 번호
화합물명
19(H13-61)(3S)-1-((5-메틸푸란-2-일)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
19(H13-62)(3S)-1-(2-(피리딘-3-일)에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
[표 1B-1]
[표 1B-2]
[표 1B-3]
[표 1B-4]
[표 1B-5]
[표 1B-6]
[표 1B-7]
[표 2B-1]
[표 2B-2]
[표 2B-3]
[표 2B-4]
[표 2B-5]
[표 2B-6]
[표 2B-7]
[표 2B-8]
[표 3B-1]
[표 3B-2]
[표 3B-3]
[표 3B-4]
[표 3B-5]
[표 3B-6]
[표 3B-7]
[표 3B-8]
[표 4B-1]
[표 4B-2]
[표 4B-3]
[표 4B-4]
[표 4B-5]
[표 4B-6]
[표 4B-7]
[표 4B-8]
[표 5B-1]
[표 5B-2]
[표 5B-3]
[표 5B-4]
[표 5B-5]
[표 5B-6]
[표 5B-7]
[표 5B-8]
[표 6B-1]
[표 6B-2]
[표 6B-3]
[표 6B-4]
[표 6B-5]
[표 6B-6]
[표 6B-7]
[표 6B-8]
[표 7B-1]
[표 7B-2]
[표 7B-3]
[표 7B-4]
[표 7B-5]
[표 7B-6]
[표 7B-7]
[표 7B-8]
[표 8B-1]
[표 8B-2]
[표 8B-3]
[표 8B-4]
[표 8B-5]
[표 8B-6]
[표 8B-7]
[표 8B-8]
[표 9B-1]
[표 9B-2]
[표 9B-3]
[표 9B-4]
[표 9B-5]
[표 9B-6]
[표 9B-7]
[표 10B-1]
[표 10B-2]
[표 10B-3]
[표 10B-4]
[표 10B-5]
[표 10B-6]
[표 10B-7]
[표 10B-8]
[표 11B-1]
[표 11B-2]
[표 11B-3]
[표 11B-4]
[표 11B-5]
[표 11B-6]
[표 11B-7]
[표 12B-1]
[표 12B-2]
[표 12B-3]
[표 12B-4]
[표 12B-5]
[표 12B-6]
[표 12B-7]
[표 12B-8]
[표 13B-1]
[표 13B-2]
[표 13B-3]
[표 13B-4]
[표 13B-5]
[표 13B-6]
[표 13B-7]
[표 1C-1]
[표 1C-2]
[표 1C-3]
[표 2C-1]
[표 2C-2]
[표 2C-3]
[표 3C-1]
[표 3C-2]
[표 3C-3]
[표 4C-1]
[표 4C-2]
[표 4C-3]
[표 5C-1]
[표 5C-2]
[표 5C-3]
[표 6C-1]
[표 6C-2]
[표 6C-3]
[표 7C-1]
[표 7C-2]
[표 7C-3]
[표 8C-1]
[표 8C-2]
[표 8C-3]
[표 9C-1]
[표 9C-2]
[표 9C-3]
[표 10C-1]
[표 10C-2]
[표 10C-3]
[표 11C-1]
[표 11C-2]
[표 11C-3]
[표 12C-1]
[표 12C-2]
[표 12C-4]
[표 13C-1]
[표 13C-2]
[표 13C-3]
실시예 20
(3S)-1-프로필-2,5-디옥소-3-(4-(벤질카르보닐아미노)부틸)-9-(2,4,6-트리메톡시벤질)-1,4,9-트리아자스피로[5.5]운데칸
실시예 8에서 제조한 화합물(0.01 g)의 디클로로에탄(0.2 ml) 용액에 2,4,6-트리메톡시벤즈알데히드(0.013 g), 트리아세톡시수소화붕소나트륨(0.015 g), 디메틸포름아미드(0.2 ml)를 첨가하였다. 반응 혼합물을 실온에서 50시간 교반하였다. 반응 혼합물을 미리 메탄올(3 ml)로 세정한 이온 교환수지(OASIS MCX, Waters, 60 mg)에 흡착시켰다. 메탄올(2 ml)로 세정하고, 10% 트리에틸아민-메탄올 용액(2 ml)으로 용출하였다. 용출액을 농축하여 이하의 물성치를 갖는 본 발명 화합물(4.4 mg)을 얻었다.
TLC: Rf 0.33(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.33(m, 5H), 6.21(s, 2H), 5.05(s, 2H), 4.00(m, 1H), 3.80(s, 9H), 3.59(s, 2H), 3.40(m, 2H), 3.11(t, J=6.6Hz, 2H), 3.05-2.75(m, 4H), 2.40-2.00(m, 2H), 2.00-1.70(m, 4H), 1.65-1.25(m, 6H), 0.90(t, J=7.2Hz, 3H).
실시예 20(1)
(3S)-1-프로필-2,5-디옥소-3-(4-(벤질카르보닐아미노)부틸)-9-(2,2-디메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸
실시예 8에서 제조한 화합물(0.01 g)과 피발알데히드(8 μl)를 이용하여 실시예 20과 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물(2.5 mg)을 얻었다.
TLC: Rf 0.53(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.33(m, 5H), 5.06(s, 2H), 4.02(m, 1H), 3.50-3.30(m, 2H), 3.20-3.00(m, 4H), 3.00-2.60(m, 4H), 2.20-2.00(m, 2H), 1.90-1.70(m, 3H), 1.70-1.20(m, 7H), 0.92(t, J=7.4Hz, 3H), 0.90(s, 9H).
실시예 20(H14-1)∼20(H15-77)
실시예 8 또는 8(1)에서 제조한 화합물과 해당하는 알데히드 유도체를 이용하여 실시예 20과 동일한 조작을 하여 이하의 표 14A-1∼15A-10에 화합물명을 나타내고 표 14B-1∼15B-12에 구조식을 나타낸 본 발명 화합물을 얻었다. 또한, 이들의 본 발명 화합물의 물성치를 이하의 표 14C-1∼15C-3에 나타내었다.
[표 14A-1]
실시예 번호
화합물명
20(H14-1)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2,4,6-트리메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-2)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3-시아노페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-3)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3-메틸부틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-4)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-(1-카르복시메틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-5)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-디메틸아미노페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-6)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3-페녹시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-7)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2E)-2-메틸부테닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 14A-2]
실시예 번호
화합물명
20(H14-8)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((1S,5S)-6,6-디메틸비시클로[3.3.1]-2-헵텐-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-9)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(1-카르복시메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-10)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-시클로프로필메틸-1,4,9-트리아자스피로[5.5]운데칸
20(H14-11)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3-메틸티오프로필)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-12)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3-카르복시프로필)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-13)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2,6-디메틸-5-헵테닐)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-14)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(퀴놀린-2-일)-1,4,9-트리아자스피로[5.5]운데칸
[표 14A-3]
실시예 번호
화합물명
20(H14-15)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2S,3R,4R,5R)-2-아세틸아미노-3,4,5,6-테트라히드록시헥사닐)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-16)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2,2-디메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-17)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4Z)-데세닐)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-18)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-19)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-부틸-1,4,9-트리아자스피로[5.5]운데칸
20(H14-20)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
20(H14-21)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2E)-3-(4-디메틸아미노페닐)프로페닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 14A-4]
실시예 번호
화합물명
20(H14-22)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2E)-3-(푸란-2-일)프로페닐)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-23)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3-히드록시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-24)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-히드록시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-25)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-디히드록시보란페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-26)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-헵틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-27)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(벤조푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-28)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3-메틸벤조티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 14A-5]
실시예 번호
화합물명
20(H14-29)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-(4-클로로페닐티오)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-30)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3,7-디메틸-6-옥테닐)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-31)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-(피롤리딘-1-일)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-32)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-메틸-3-(4-(2,2-디메틸프로필)페닐)프로필)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-33)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-벤질옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-34)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-히드록시-3,5-비스(1,1-디메틸에틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 14A-6]
실시예 번호
화합물명
20(H14-35)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-메틸-3-(4-(1-메틸에틸)페닐)프로필)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-36)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3,4-디-(벤질옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-37)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-옥틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-38)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3,5,5-트리메틸헥실)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-39)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-부틸옥시카르보닐메틸-1,4,9-트리아자스피로[5.5]운데칸
20(H14-40)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-(4-히드록시-4-메틸펜틸)-3-시클로헥세닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-41)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(5-히드록시펜틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 14A-7]
실시예 번호
화합물명
20(H14-42)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-((1R,2S,3R,5R)-2-히드록시-4,6,8-트리옥사스피로[비시클로[3.3.0]옥탄-7,1'-시클로헥산]-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-43)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-44)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-(1,1-디메틸에틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-45)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-46)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-(2,2,6-트리메틸-1-시클로헥세닐)에틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-47)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-(3-디메틸아미노프로필옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 14A-8]
실시예 번호
화합물명
20(H14-48)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-49)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-50)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-시클로헥실메틸-1,4,9-트리아자스피로[5.5]운데칸
20(H14-51)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(티아졸-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-52)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-아세틸아미노페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-53)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-54)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 14A-9]
실시예 번호
화합물명
20(H14-55)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-비페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-56)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2E,6E)-3,7-디메틸-2,6-옥타디에닐)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-57)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-디메틸아미노페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-58)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-에틸헥실)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-59)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3-플루오로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-60)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-히드록시에틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-61)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(나프탈렌-1-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 14A-10]
실시예 번호
화합물명
20(H14-62)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-프로필-1,4,9-트리아자스피로[5.5]운데칸
20(H14-63)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2S,3S,4R)-2,3,4,5-테트라히드록시펜틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-64)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-65)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2E)-데세닐)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-66)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-클로로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-67)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(1,3-벤조디옥소렌-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-68)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((3S,4R)-3,4,5-트리히드록시펜틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 14A-11]
실시예 번호
화합물명
20(H14-69)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2,3-디메틸-5-옥소-1-페닐-3-피라졸린-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-70)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-((2E)-4-메틸펜테닐)-3-시클로헥세닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-71)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3-메톡시-4-헥실옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-72)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-플루오로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-73)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3,5,6-트리메틸-3-시클로헥세닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-74)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-75)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-벤질옥시에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 14A-12]
실시예 번호
화합물명
20(H14-76)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3-메톡시-4-벤질옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-77)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3-벤질옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-78)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-벤질옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-79)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H14-80)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-알릴옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 15A-1]
실시예 번호
화합물명
20(H15-1)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2,4,6-트리메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-2)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(3-시아노페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-3)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(3-메틸부틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-4)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2-(1-카르복시메틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-5)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-디메틸아미노페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-6)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(3-페녹시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-7)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2E)-2-메틸부테닐)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-8)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((1S,5S)-6,6-디메틸비시클로[3.3.1]-2-헵텐-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 15A-2]
실시예 번호
화합물명
20(H15-9)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(1-카르복시메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-10)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-시클로프로필메틸-1,4,9-트리아자스피로[5.5]운데칸
20(H15-11)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(3-메틸티오프로필)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-12)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(3-카르복시프로필)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-13)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2,6-디메틸-5-헵테닐)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-14)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(퀴놀린-2-일)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-15)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2S,3R,4R,5R)-2-아세틸아미노-3,4,5,6-테트라히드록시헥사닐)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-16)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2,2-디메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-17)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((4Z)-데세닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 15A-3]
실시예 번호
화합물명
20(H15-18)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-19)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-부틸-1,4,9-트리아자스피로[5.5]운데칸
20(H15-20)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
20(H15-21)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2E)-3-(푸란-2-일)프로페닐)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-22)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(3-히드록시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-23)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2-히드록시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-24)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-디히드록시보란페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-25)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-헵틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-26)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(벤조푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 15A-4]
실시예 번호
화합물명
20(H15-27)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(3-메틸벤조티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-28)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2-(4-클로로페닐티오)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-29)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(3,7-디메틸-6-옥테닐)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-30)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-(피롤리딘-1-일)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-31)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2-메틸-3-(4-(2,2-디메틸프로필)페닐)프로필)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-32)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2-벤질옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-33)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-히드록시-3,5-디-(1,1-디메틸에틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-34)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2-메틸-3-(4-(1-메틸에틸)페닐)프로필)-1,4,9-트리아자스피로[5.5]운데칸
[표 15A-5]
실시예 번호
화합물명
20(H15-35)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(3,4-디-(벤질옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-36)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-옥틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-37)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(3,5,5-트리메틸헥실)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-38)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-부틸옥시카르보닐메틸-1,4,9-트리아자스피로[5.5]운데칸
20(H15-39)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-히드록시-4-메틸펜틸)-3-시클로헥세닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-40)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(5-히드록시펜틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-41)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2-((1R,2S,3R,5R)-2-히드록시-4,6,8-트리옥사스피로[비시클로[3.3.0]옥탄-7,1'-시클로헥산]-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-42)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(3-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 15A-6]
실시예 번호
화합물명
20(H15-43)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-(1,1-디메틸에틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-44)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-45)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2-(2,2,6-트리메틸-1-시클로헥세닐)에틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-46)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-(3-디메틸아미노프로필옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-47)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-48)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2-메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-49)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-시클로헥실메틸-1,4,9-트리아자스피로[5.5]운데칸
20(H15-50)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(티아졸-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 15A-7]
실시예 번호
화합물명
20(H15-51)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-아세틸아미노페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-52)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-53)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-54)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-비페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-55)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2-에틸헥실)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-56)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(3-플루오로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-57)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2-히드록시에틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-58)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(나프탈렌-1-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-59)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-프로필-1,4,9-트리아자스피로[5.5]운데칸
[표 15A-8]
실시예 번호
화합물명
20(H15-60)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2S,3S,4R)-2,3,4,5-테트라히드록시펜틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-61)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-62)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2E)-데세닐)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-63)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-클로로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-64)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(1,3-벤조디옥소렌-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-65)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((3S,4R)-3,4,5-트리히드록시펜틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-66)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2,3-디메틸-5-옥소-1-페닐-3-피라졸린-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-67)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-((2E)-4-메틸펜테닐)-3-시클로헥세닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 15A-9]
실시예 번호
화합물명
20(H15-68)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(3-메톡시-4-헥실옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-69)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-플루오로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-70)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(3,5,6-트리메틸-3-시클로헥세닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-71)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-72)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2-벤질옥시에틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-73)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(3-메톡시-4-벤질옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-74)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(3-벤질옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-75)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-벤질옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 15A-10]
실시예 번호
화합물명
20(H15-76)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
20(H15-77)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-알릴옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 14B-1]
[표 14B-2]
[표 14B-3]
[표 14B-4]
[표 14B-5]
[표 14B-6]
[표 14B-7]
[표 14B-8]
[표 14B-9]
[표 14B-10]
[표 14B-11]
[표 15B-1]
[표 15B-2]
[표 15B-3]
[표 15B-4]
[표 15B-5]
[표 15B-6]
[표 15B-7]
[표 15B-8]
[표 15B-9]
[표 15B-10]
[표 15B-11]
[표 15B-12]
[표 14C-1]
[표 14C-2]
[표 14C-3]
[표 14C-4]
[표 15C-1]
[표 15C-2]
[표 15C-3]
실시예 21
(3S)-1-프로필-2,5-디옥소-3-(4-(벤질카르보닐아미노)부틸)-9-(3-페닐프로파노일)-1,4,9-트리아자스피로[5.5]운데칸
실시예 8에서 제조한 화합물(0.01 g)의 디클로로에탄(0.2 ml) 용액에 디이소프로필에틸아민(6 μl), 3-페닐프로파노일클로라이드(5 μl)를 첨가하였다. 반응 혼합물을 실온에서 1시간 교반하였다. 반응 혼합물을 아미노메틸화폴리스티렌-2% 디비닐벤젠 공중합수지(NovaBiochem, AM Resin, 50 mg)에 첨가하여 디클로로에탄으로 세정하고, 여과하였다. 여과액을 농축하여 이하의 물성치를 갖는 본 발명 화합물(14 mg)을 얻었다.
TLC: Rf 0.55(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.40-7.10(m, 10H), 5.06(s, 2H), 4.03(m, 1H), 3.70-3.55(m, 2H), 3.28-3.00(m, 5H), 3.00-2.80(m, 3H), 2.80-2.60(m, 2H), 2.00-1.65(m, 6H), 1.65-1.40(m, 6H), 0.90(t, J=7.2Hz, 3H).
실시예 21(1)
(3S)-1-프로필-2,5-디옥소-3-(4-(벤질카르보닐아미노)부틸)-9-벤젠설포닐-1,4,9-트리아자스피로[5.5]운데칸
실시예 8에서 제조한 화합물(0.01 g), 디이소프로필에틸아민(6 μl)벤젠설포닐클로라이드(4.5 μl)를 이용하여 실시예 21과 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물(16 mg)을 얻었다.
TLC: Rf 0.58(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.80(m, 2H), 7.63(m, 3H), 7.33(m, 5H), 5.04(s, 2H), 3.98(t, J=4.8Hz, 1H), 3.60-3.35(m, 2H), 3.28-2.90(m, 6H), 2.20-1.65(m, 6H), 1.65-1.20(m, 6H), 0.89(t, J=7.2Hz, 3H).
실시예 21(2)
(3S)-1-프로필-2,5-디옥소-3-(4-(벤질카르보닐아미노)부틸)-9-벤질아미노카르보닐-1,4,9-트리아자스피로[5.5]운데칸
실시예 8에서 제조한 화합물(0.01 g)과 벤질이소시아네이트(4 μl)를 이용하여, 실시예 21와 동일하게 조작을 하여 이하의 물성치를 갖는 본 발명 화합물(16 mg)을 얻었다.
TLC: Rf 0.45(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.40-7.10(m, 10H), 5.05(s, 2H), 4.37(s, 2H), 4.10-3.90(m, 3H), 3.60-3.45(m, 2H), 3.30-3.00(m, 4H), 2.10-1.70(m, 6H), 1.65-1.20(m, 6H), 0.87(t, J=7.4Hz, 3H).
실시예 21(H16-1)∼21(H19-71)
실시예 8 또는 8(1)에서 제조한 화합물과 해당하는 산클로라이드 유도체, 설포닐클로라이드 유도체 또는 이소시아네이트 유도체를 이용하여 실시예 21, 21(1) 또는 21(2)과 동일한 조작을 하여 이하의 표 16A-1∼19A-9에 화합물명을 나타내고, 표 16B-1∼19B-11에 구조식을 나타낸 본 발명 화합물을 얻었다. 또한, 이들의 본 발명 화합물의 물성치를 이하의 표 16C-1∼19C-3에 나타내었다.
[표 16A-1]
실시예 번호
화합물명
21(H16-1)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-페닐페닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-2)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-디메틸아미노페닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-3)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((3-(2-클로로페닐)-5-메틸이소옥사졸-4-일)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-4)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-플루오로페닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-5)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((3-플루오로페닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-6)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2-플루오로페닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-7)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(시클로펜틸카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 16A-2]
실시예 번호
화합물명
21(H16-8)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((3-메틸페닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-9)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((3-메톡시페닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-10)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2,2-디메틸프로파노일)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-11)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(피리딘-3-일카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-12)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(피리딘-4-일카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-13)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(피리딘-2-일카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-14)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐아세틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 16A-3]
실시예 번호
화합물명
21(H16-15)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐옥시아세틸)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-16)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-에틸-2,3-디옥소피페라지닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-17)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2-페닐티오피리딘-3-일)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-18)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2-페닐옥시피리딘-3-일)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-19)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2-메톡시페닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-20)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-(티오펜-2-일)아세틸)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-21)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-헥사노일-1,4,9-트리아자스피로[5.5]운데칸
[표 16A-4]
실시예 번호
화합물명
21(H16-22)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-메틸페닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-23)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-메틸프로파노일)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-24)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3-시클로펜틸프로파노일)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-25)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2E)3-페닐-2-프로페노일)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-26)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2-메틸페닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-27)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3,3-디메틸부테노일)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-28)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(시클로헥실카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 16A-5]
실시예 번호
화합물명
21(H16-29)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(페닐카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-30)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(티오펜-2-일카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-31)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2,6,6-트리메틸-1-시클로헥세닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-32)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(에톡시옥살릴)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-33)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((3-페닐-5-메틸이소옥사졸-4-일)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-34)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((5-메틸-2-페닐-1,2,3-트리아졸-4-일)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-35)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-(3-메톡시페닐)아세틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 16A-6]
실시예 번호
화합물명
21(H16-36)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-메톡시페닐카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-37)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((푸란-2-일)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-38)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-벤질옥시아세틸)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-39)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(시클로부틸카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-40)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-(4-메톡시페닐)아세틸)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-41)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-아세틸-1,4,9-트리아자스피로[5.5]운데칸
21(H16-42)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(4-메틸펜타놀)-1,4,9-트리아자스피로[5.5]운데칸
[표 16A-7]
실시예 번호
화합물명
21(H16-43)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-메톡시아세틸)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-44)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3-메틸티오프로파노일)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-45)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((이소옥사졸-5-일)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-46)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-시클로펜틸아세틸)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-47)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-펜타놀-1,4,9-트리아자스피로[5.5]운데칸
21(H16-48)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(3-메틸부타노일)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-49)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐티오아세틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 16A-8]
실시예 번호
화합물명
21(H16-50)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-메틸-1,2,3-티아디아졸-5-일)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-51)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((3-시아노페닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-52)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-부탄올-1,4,9-트리아자스피로[5.5]운데칸
21(H16-53)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-프로파노일-1,4,9-트리아자스피로[5.5]운데칸
21(H16-54)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(시클로프로필카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-55)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2H-벤조[3,4-d]1,3-디옥솔란-5-일카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-56)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((1-페닐-5-프로필피라졸-4-일)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 16A-9]
실시예 번호
화합물명
21(H16-57)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((5-(1,1-디메틸에틸)-2-메틸푸란-3-일)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-58)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((1-(1,1-디메틸에틸)-3-메틸피라졸-5-일)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-59)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-메틸설포닐-1,4,9-트리아자스피로[5.5]운데칸
21(H16-60)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-펜틸설포닐-1,4,9-트리아자스피로[5.5]운데칸
21(H16-61)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((1-메틸에틸)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-62)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-클로로페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-63)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2-요오드페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 16A-10]
실시예 번호
화합물명
21(H16-64)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-니트로페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-65)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-메틸설포닐페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-66)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-트리플루오로메틸페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-67)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-비페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-68)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2-비페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-69)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2-메톡시카르보닐페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-70)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((3,4-디플루오로페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 16A-11]
실시예 번호
화합물명
21(H16-71)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2,6-디플루오로페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-72)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2,5-디플루오로페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-73)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2,5-디메톡시페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-74)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2-클로로-4-트리플루오로메틸페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-75)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-나프틸설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-76)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(((1E)-2-페닐비닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H16-77)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((푸란-2-일)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 16A-12]
실시예 번호
화합물명
21(H16-78)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((티오펜-2-일)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 17A-1]
실시예 번호
화합물명
21(H17-1)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-브로모-2,5-디클로로티오펜-3-일)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-2)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((5-페닐설포닐티오펜-2-일)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-3)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((7-클로로벤조프라잔-4-일)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-4)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-메틸-2-아세틸아미노티아졸-5-일)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-5)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2-메톡시-디벤조푸란-3-일)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-6)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((3,4-디클로로페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-7)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-메톡시페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 17A-2]
실시예 번호
화합물명
21(H17-8)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-벤질설포닐-1,4,9-트리아자스피로[5.5]운데칸
21(H17-9)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((에틸아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-10)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((프로필아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-11)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((1-메틸에틸아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-12)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((에톡시카르보닐메틸아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-13)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((부틸아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-14)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-클로로페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 17A-3]
실시예 번호
화합물명
21(H17-15)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-16)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-메틸페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-17)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((헥실아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-18)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-플루오로페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-19)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((벤질아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-20)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((시클로헥실아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-21)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((3-메틸페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 17A-4]
실시예 번호
화합물명
21(H17-22)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((옥틸아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-23)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-브로모페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-24)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2-(티오펜-2-일)에틸아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-25)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-(1-메틸에틸)페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-26)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((3-클로로페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-27)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2,4,5-트리메틸페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-28)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2,4,6-트리메틸페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 17A-5]
실시예 번호
화합물명
21(H17-29)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-페닐옥시페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-30)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-부틸옥시페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-31)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-페닐페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-32)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2-페닐페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-33)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-트리플루오로메틸페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-34)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((3,4-디클로로페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-35)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-부틸옥시카르보닐페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 17A-6]
실시예 번호
화합물명
21(H17-36)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2,6-디(1-메틸에틸)페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-37)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2,5-디메틸페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-38)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2-에틸-6-(1-메틸에틸)페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-39)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2,4,6-트리클로로페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-40)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((3,4-디메틸페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-41)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2-메틸티오페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-42)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-메틸티오페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 17A-7]
실시예 번호
화합물명
21(H17-43)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((4-부틸페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-44)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2-클로로-5-트리플루오로메틸페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-45)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2,6-디브로모-4-에틸페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-46)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((1-에톡시카르보닐-2-메틸프로필아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-47)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((페닐카르보닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-48)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2,4,6-트리브로모페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-49)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2,5-디플루오로페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 17A-8]
실시예 번호
화합물명
21(H17-50)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((3,5-비스(메톡시카르보닐)페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-51)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((6,7-메틸렌디옥시쿠마린-4-일메틸아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-52)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2,6-디메틸페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-53)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2-메틸프로필옥시)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-54)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2-에틸헥실옥시)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-55)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(에톡시카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-56)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(알릴옥시카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 17A-9]
실시예 번호
화합물명
21(H17-57)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(프로필옥시카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-58)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(부틸옥시카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-59)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(헥실옥시카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-60)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2,2,2-트리클로로에틸옥시)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-61)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((플루오렌-9-일메틸옥시)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-62)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((1R,5R,2S)-5-메틸-2-(1-메틸에틸)시클로헥실옥시카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-63)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2-메톡시에톡시)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 17A-10]
실시예 번호
화합물명
21(H17-64)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(펜틸옥시카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-65)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((1-메틸에틸옥시)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-66)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((3-부테닐옥시)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-67)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((2R,1S,5S)-메틸-2-(1-메틸에틸)시클로헥실옥시카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-68)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(시클로펜틸옥시카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-69)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((1,1-디메틸에틸옥시)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-70)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(벤질옥시카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 17A-11]
실시예 번호
화합물명
21(H17-71)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((N,N-디페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-72)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((N-페닐-N-메틸아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-73)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((N,N-디메틸아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-74)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((N,N-디에틸아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-75)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-((N,N-비스(1-메틸에틸)아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-76)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(모르폴린-4-일카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H17-77)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(카르바졸-9-일카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 17A-12]
실시예 번호
화합물명
21(H17-78)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(피롤리딘-1-일카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 18A-1]
실시예 번호화합물명
21(H18-1)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((4-비페닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-2)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((4,7,7-트리메틸-2-옥사-3-옥소비시클로[2.2.1]헵탄-1-일)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-3)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((4-디메틸아미노페닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-4)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((3-(2-클로로페닐)-5-메틸이소옥사졸-4-일)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-5)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((4-플루오로페닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-6)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((3-플루오로페닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-7)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2-플루오로페닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-8)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(시클로펜틸카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 18A-2]
실시예 번호
화합물명
21(H18-9)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((3-메틸페닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-10)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((3-메톡시페닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-11)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2,2-디메틸프로파노일)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-12)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(피리딘-3-일카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-13)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(피리딘-2-일카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-14)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐아세틸)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-15)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐옥시아세틸)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-16)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((4-에틸-2,3-디옥소피페라지닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-17)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2-페닐티오피리딘-3-일)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 18A-3]
실시예 번호
화합물명
21(H18-18)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2-페닐옥시피리딘-3-일)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-19)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2-메톡시페닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-20)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2-(티오펜-2-일)아세틸)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-21)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-헥사노일-1,4,9-트리아자스피로[5.5]운데칸
21(H18-22)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((4-메틸페닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-23)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2-메틸프로파노일)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-24)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(3-시클로펜틸프로파노일)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-25)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2E)-3-페닐-2-프로페노일)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-26)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2-메틸페닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 18A-4]
실시예 번호
화합물명
21(H18-27)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(3,3-디메틸부타노일)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-28)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-시클로헥실카르보닐-1,4,9-트리아자스피로[5.5]운데칸
21(H18-29)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-페닐카르보닐-1,4,9-트리아자스피로[5.5]운데칸
21(H18-30)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(티오펜-2-일카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-31)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2,6,6-트리메틸-1-시클로헥세닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-32)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((에톡시카르보닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-33)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((3-페닐-5-메틸이소옥사졸-4-일)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-34)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((5-메틸-2-페닐-1,2,3-트리아졸-4-일)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 18A-5]
실시예 번호
화합물명
21(H18-35)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2-(3-메톡시페닐)아세틸)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-36)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-메톡시페닐카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-37)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((푸란-2-일)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-38)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2-벤질옥시아세틸)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-39)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(시클로부틸카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-40)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2-(4-메톡시페닐)아세틸)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-41)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-아세틸-1,4,9-트리아자스피로[5.5]운데칸
21(H18-42)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-메틸펜타노일)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-43)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2-메톡시아세틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 18A-6]
실시예 번호
화합물명
21(H18-44)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(3-메틸티오프로파노일)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-45)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((이소옥사졸-5-일)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-46)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2-시클로펜틸아세틸)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-47)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-펜타노일-1,4,9-트리아자스피로[5.5]운데칸
21(H18-48)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(3-메틸프로파노일)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-49)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐티오아세틸)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-50)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((4-메틸-1,2,3-티아디아졸-5-일)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-51)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((3-시아노페닐)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-52)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-부타노일-1,4,9-트리아자스피로[5.5]운데칸
[표 18A-7]
실시예 번호
화합물명
21(H18-53)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-프로파노일-1,4,9-트리아자스피로[5.5]운데칸
21(H18-54)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-시클로프로필카르보닐-1,4,9-트리아자스피로[5.5]운데칸
21(H18-55)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2H-벤조[3,4-d]1,3-디옥솔란-5-일카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-56)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((1-페닐-5-프로필피라졸-4-일)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-57)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((5-(1,1-디메틸에틸)-2-메틸푸란-3-일)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-58)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((1-(1,1-디메틸에틸)-3-메틸피라졸-5-일)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-59)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-메틸설포닐-1,4,9-트리아자스피로[5.5]운데칸
21(H18-60)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-펜틸설포닐-1,4,9-트리아자스피로[5.5]운데칸
[표 18A-8]
실시예 번호
화합물명
21(H18-61)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((1-메틸에틸)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-62)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2-요오드페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-63)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((4-메틸설포닐페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-64)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((4-트리플루오로메틸페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-65)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((4-페닐페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-66)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2-페닐페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-67)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2-메톡시카르보닐페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-68)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((3,4-디플루오로페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-69)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2,6-디플루오로페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 18A-9]
실시예 번호
화합물명
21(H18-70)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2,5-디플루오로페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-71)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2,5-디메톡시페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-72)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2-나프틸설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-73)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(((1E)-2-페닐비닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-74)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((푸란-2-일)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H18-75)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((티오펜-2-일)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 19A-1]
실시예 번호
화합물명
21(H19-1)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((4-메틸-2-아세틸아미노티아졸-5-일)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-2)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2-메톡시-디벤조푸란-3-일)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-3)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((4-메톡시페닐)설포닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-4)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-벤질설포닐-1,4,9-트리아자스피로[5.5]운데칸
21(H19-5)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((에틸아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-6)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((프로필아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-7)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((1-메틸에틸아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-8)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((에톡시카르보닐메틸아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 19A-2]
실시예 번호
화합물명
21(H19-9)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((부틸아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-10)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((4-클로로페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-11)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-12)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((4-메틸페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-13)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((헥실아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-14)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((4-플루오로페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-15)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((벤질아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-16)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((시클로헥실아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-17)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((3-메틸페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 19A-3]
실시예 번호
화합물명
21(H19-18)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((옥틸아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-19)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((4-브로모페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-20)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2-(티오펜-2-일)에틸아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-21)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((4-(1-메틸에틸)페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-22)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((3-클로로페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-23)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2,4,5-트리메틸페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-24)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2,4,6-트리메틸페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-25)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((4-페닐옥시페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 19A-4]
실시예 번호
화합물명
21(H19-26)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((4-부틸옥시페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-27)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((4-페닐페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-28)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2-페닐페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-29)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((4-트리플루오로메틸페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-30)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((3,4-디클로로페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-31)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((4-부틸옥시카르보닐페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-32)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2,6-비스(1-메틸에틸)페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-33)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2,5-디메틸페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 19A-5]
실시예 번호
화합물명
21(H19-34)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2-에틸-6-(1-메틸에틸)페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-35)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2,4,6-트리클로로페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-36)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((3,4-디메틸페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-37)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2-메틸티오페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-38)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((4-메틸티오페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-39)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((4-부틸페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-40)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2,6-디브로모-4-에틸페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-41)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((1-에톡시카르보닐-2-메틸프로필아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 19A-6]
실시예 번호
화합물명
21(H19-42)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((페닐카르보닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-43)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2,4,6-트리브로모페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-44)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2,5-디플루오로페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-45)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((3,5-비스(메톡시카르보닐)페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-46)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((6,7-메틸렌디옥시쿠마린-4-일메틸아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-47)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2,6-디메틸페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-48)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2-메틸프로필옥시)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-49)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2-에틸헥실옥시)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 19A-7]
실시예 번호
화합물명
21(H19-50)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-에톡시카르보닐-1,4,9-트리아자스피로[5.5]운데칸
21(H19-51)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-알릴옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸
21(H19-52)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-프로필옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸
21(H19-53)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-부틸옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸
21(H19-54)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-헥실옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸
21(H19-55)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((플루오렌-9-일메틸옥시)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-56)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((1R,5R,2S)-5-메틸-2-(1-메틸에틸)시클로헥실옥시카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-57)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2-메톡시에톡시)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-58)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-펜틸옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸
[표 19A-8]
실시예 번호
화합물명
21(H19-59)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((1-메틸에틸옥시)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-60)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((3-부테닐옥시)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-61)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((2R,1S,5S)-메틸-2-(1-메틸에틸)시클로헥실옥시카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-62)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-시클로펜틸옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸
21(H19-63)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-벤질옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸
21(H19-64)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((N,N-디페닐아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-65)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((N-페닐-N-메틸아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-66)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((N,N-디메틸아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-67)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((N,N-디에틸아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 19A-9]
실시예 번호
화합물명
21(H19-68)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-((N,N-비스(1-메틸에틸)아미노)카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-69)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(모르폴린-4-일카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-70)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(카르바졸-9-일카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
21(H19-71)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(피롤리딘-1-일카르보닐)-1,4,9-트리아자스피로[5.5]운데칸
[표 16B-1]
[표 16B-2]
[표 16B-3]
[표 16B-4]
[표 16B-5]
[표 16B-6]
[표 16B-7]
[표 16B-8]
[표 16B-9]
[표 16B-10]
[표 16B-11]
[표 16B-12]
[표 17B-1]
[표 17B-2]
[표 17B-3]
[표 17B-4]
[표 17B-5]
[표 17B-6]
[표 17B-7]
[표 17B-8]
[표 17B-9]
[표 17B-10]
[표 17B-11]
[표 17B-12]
[표 18B-1]
[표 18B-2]
[표 18B-3]
[표 18B-4]
[표 18B-5]
[표 18B-6]
[표 18B-7]
[표 18B-8]
[표 18B-9]
[표 18B-10]
[표 18B-11]
[표 19B-1]
[표 19B-2]
[표 19B-3]
[표 19B-4]
[표 19B-5]
[표 19B-6]
[표 19B-7]
[표 19B-8]
[표 19B-9]
[표 19B-10]
[표 19B-11]
[표 16C-1]
[표 16C-2]
[표 16C-3]
[표 17C-1]
[표 17C-2]
[표 17C-3]
[표 18C-1]
[표 18C-2]
[표 18C-3]
[표 19C-1]
[표 19C-2]
[표 19C-3]
실시예 22
(3S)-1-프로필-2,5-디옥소-3-(4-(3-페닐프로파노일)아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
실시예 14에서 제조한 화합물(5 mg)의 디클로로에탄(0.5 ml) 용액에피리딘(2 μl), 3-페닐프로파노일클로라이드(4 μl)를 첨가하였다. 반응 혼합물을 실온에서 3시간 교반하였다. 반응 혼합물에 메탄올을 첨가하여 미리 메탄올(3 ml)로 세정한 이온 교환수지(OASIS MCX, Waters, 60 mg)에 흡착시켰다. 메탄올(2 ml)로 세정하고, 10% 트리에틸아민-메탄올 용액(2 ml)으로 용출하였다. 용출액을 농축하여 이하의 물성치를 갖는 본 발명 화합물(1.6 mg)을 얻었다.
TLC: Rf 0.49(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.40-7.10(m, 10H), 4.03(m, 1H), 3.60-3.30(m, 2H), 3.14(m, 2H), 3.06-2.90(m, 3H), 2.90-2.75(m, 4H), 2.75-2.60(m, 3H), 2.45(t, J=7.4Hz, 2H), 2.30-2.00(m, 2H), 2.00-1.70(m, 4H), 1.70-1.20(m, 6H), 0.93(t, J=7.2Hz, 3H).
실시예 22(1)
(3S)-1-프로필-2,5-디옥소-3-(4-벤젠설포닐아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
실시예 14에서 제조한 화합물(5 mg), 피리딘(2 μl), 벤젠설포닐클로라이드(3 μl)를 이용하여 실시예 22와 동일한 조작을 하여 이하의물성치를 갖는 본 발명 화합물(4.4 mg)을 얻었다.
TLC: Rf 0.49(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.84(m, 2H), 7.59(m, 3H), 7.34-7.10(m, 5H), 4.01(t, J=5.0Hz, 1H), 3.55-3.30(m, 2H), 3.05-2.90(m, 3H), 2.90-2.75(m, 4H), 2.75-2.60(m, 3H), 2.30-2.00(m, 2H), 1.96(m, 2H), 1.88-1.70(m, 2H), 1.70-1.20(m, 6H), 0.94(t, J=7.4Hz, 3H).
실시예 22(2)
(3S)-1-프로필-2,5-디옥소-3-(4-(N-벤질카르바모일)아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
실시예 14에서 제조한 화합물(5 mg), 벤질이소시아네이트(3 μl)를 이용하여 실시예 22와 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물(7 mg)을 얻었다.
TLC: Rf 0.46(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.40-7.10(m, 10H), 4.30(s, 2H), 4.04(t, J=5.0Hz, 1H),3.55-3.30(m, 2H), 3.15(t, J=6.6Hz, 3H), 3.05-2.90(m, 3H), 2.90-2.75(m, 3H), 2.75-2.60(m, 2H), 2.35-2.05(m, 2H), 2.02-1.70(m, 4H), 1.70-1.20(m, 6H), 0.93(t, J=7.4Hz, 3H).
실시예 22(H20-1)∼22(H21-77)
실시예 14에서 제조한 화합물과 해당하는 산클로라이드 유도체, 설포닐클로라이드 유도체 또는 이소시아네이트 유도체를 이용하여 실시예 22, 22(1) 또는 22(2)와 동일한 조작을 하여 이하의 표 20A-1∼21A-11에 화합물명을 나타내고 표 20B-1∼21B-12에 구조식을 나타낸 본 발명 화합물을 얻었다. 또한, 이들의 본 발명 화합물의 물성치를 이하의 표 20C-1∼21C-3에 나타내었다.
[표 20A-1]
실시예 번호
화합물명
22(H20-1)(3S)-1-프로필-2,5-디옥소-3-(4-((4-비페닐)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-2)(3S)-1-프로필-2,5-디옥소-3-(4-((4,7,7-트리메틸-2-옥사-3-옥소비시클로[2.2.1]헵탄-1-일)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-3)(3S)-1-프로필-2,5-디옥소-3-(4-((4-디메틸아미노페닐)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-4)(3S)-1-프로필-2,5-디옥소-3-(4-((3-(2-클로로페닐)-5-메틸이소옥사졸-4-일)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-5)(3S)-1-프로필-2,5-디옥소-3-(4-((4-플루오로페닐)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-6)(3S)-1-프로필-2,5-디옥소-3-(4-((3-플루오로페닐)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-7)(3S)-1-프로필-2,5-디옥소-3-(4-((2-플루오로페닐)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 20A-2]
실시예 번호
화합물명
22(H20-8)(3S)-1-프로필-2,5-디옥소-3-(4-(시클로펜틸카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-9)(3S)-1-프로필-2,5-디옥소-3-(4-((3-메틸페닐)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-10)(3S)-1-프로필-2,5-디옥소-3-(4-((3-메톡시페닐)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-11)(3S)-1-프로필-2,5-디옥소-3-(4-(2,2-디메틸프로파노일아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-12)(3S)-1-프로필-2,5-디옥소-3-(4-(피리딘-3-일카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-13)(3S)-1-프로필-2,5-디옥소-3-(4-(피리딘-2-일카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-14)(3S)-1-프로필-2,5-디옥소-3-(4-(2-페닐아세틸아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 20A-3]
실시예 번호
화합물명
22(H20-15)(3S)-1-프로필-2,5-디옥소-3-(4-(2-페닐옥시아세틸아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-16)(3S)-1-프로필-2,5-디옥소-3-(4-((4-에틸-2,3-디옥소피페라지닐)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-17)(3S)-1-프로필-2,5-디옥소-3-(4-((2-페닐티오피리딘-3-일)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-18)(3S)-1-프로필-2,5-디옥소-3-(4-((2-페닐옥시피리딘-3-일)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-19)(3S)-1-프로필-2,5-디옥소-3-(4-((2-메톡시페닐)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-20)(3S)-1-프로필-2,5-디옥소-3-(4-(2-(티오펜-2-일)아세틸아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-21)(3S)-1-프로필-2,5-디옥소-3-(4-(헥사노일아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 20A-4]
실시예 번호
화합물명
22(H20-22)(3S)-1-프로필-2,5-디옥소-3-(4-((4-메틸페닐)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-23)(3S)-1-프로필-2,5-디옥소-3-(4-(2-메틸프로파노일아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-24)(3S)-1-프로필-2,5-디옥소-3-(4-(3-시클로펜틸프로파노일아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-25)(3S)-1-프로필-2,5-디옥소-3-(4-((2E)-3-페닐-2-프로페노일아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-26)(3S)-1-프로필-2,5-디옥소-3-(4-((2-메틸페닐)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-27)(3S)-1-프로필-2,5-디옥소-3-(4-(3,3-디메틸부타노일아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-28)(3S)-1-프로필-2,5-디옥소-3-(4-(시클로헥실카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 20A-5]
실시예 번호
화합물명
22(H20-29)(3S)-1-프로필-2,5-디옥소-3-(4-(페닐카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-30)(3S)-1-프로필-2,5-디옥소-3-(4-(티오펜-2-일카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-31)(3S)-1-프로필-2,5-디옥소-3-(4-((2,6,6-트리메틸-1-시클로헥세닐)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-32)(3S)-1-프로필-2,5-디옥소-3-(4-((3-페닐-5-메틸이소옥사졸-4-일)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-33)(3S)-1-프로필-2,5-디옥소-3-(4-((5-메틸-2-페닐-1,2,3-트리아졸-4-일)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-34)(3S)-1-프로필-2,5-디옥소-3-(4-(2-(3-메톡시페닐)아세틸아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-35)(3S)-1-프로필-2,5-디옥소-3-(4-(4-메톡시페닐카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 20A-6]
실시예 번호
화합물명
22(H20-36)(3S)-1-프로필-2,5-디옥소-3-(4-((푸란-2-일)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-37)(3S)-1-프로필-2,5-디옥소-3-(4-(2-벤질옥시아세틸아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-38)(3S)-1-프로필-2,5-디옥소-3-(4-(시클로부틸카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-39)(3S)-1-프로필-2,5-디옥소-3-(4-(2-(4-메톡시페닐)아세틸아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-40)(3S)-1-프로필-2,5-디옥소-3-(4-(아세틸아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-41)(3S)-1-프로필-2,5-디옥소-3-(4-(4-메틸펜타노일아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-42)(3S)-1-프로필-2,5-디옥소-3-(4-(2-메톡시아세틸아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 20A-7]
실시예 번호
화합물명
22(H20-43)(3S)-1-프로필-2,5-디옥소-3-(4-(3-메틸티오프로파노일아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-44)(3S)-1-프로필-2,5-디옥소-3-(4-(2-시클로펜틸아세틸아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-45)(3S)-1-프로필-2,5-디옥소-3-(4-(펜타노일아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-46)(3S)-1-프로필-2,5-디옥소-3-(4-(3-메틸프로파노일아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-47)(3S)-1-프로필-2,5-디옥소-3-(4-(2-페닐티오아세틸아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-48)(3S)-1-프로필-2,5-디옥소-3-(4-((4-메틸-1,2,3-티아디아졸-5-일)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-49)(3S)-1-프로필-2,5-디옥소-3-(4-((3-시아노페닐)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 20A-8]
실시예 번호
화합물명
22(H20-50)(3S)-1-프로필-2,5-디옥소-3-(4-(부타노일아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-51)(3S)-1-프로필-2,5-디옥소-3-(4-(프로파노일아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-52)(3S)-1-프로필-2,5-디옥소-3-(4-(시클로프로필카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-53)(3S)-1-프로필-2,5-디옥소-3-(4-(2H-벤조[3,4-d]1,3-디옥솔란-5-일카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-54)(3S)-1-프로필-2,5-디옥소-3-(4-((1-페닐-5-프로필피라졸-4-일)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-55)(3S)-1-프로필-2,5-디옥소-3-(4-((5-(1,1-디메틸에틸)-2-메틸푸란-3-일)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-56)(3S)-1-프로필-2,5-디옥소-3-(4-((1-(1,1-디메틸에틸)-3-메틸피라졸-5-일)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 20A-9]
실시예 번호
화합물명
22(H20-57)(3S)-1-프로필-2,5-디옥소-3-(4-(메틸설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-58)(3S)-1-프로필-2,5-디옥소-3-(4-(펜틸설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-59)(3S)-1-프로필-2,5-디옥소-3-(4-(1-메틸에틸설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-60)(3S)-1-프로필-2,5-디옥소-3-(4-(4-클로로페닐설포닐)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-61)(3S)-1-프로필-2,5-디옥소-3-(4-(2-요오드페닐설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-62)(3S)-1-프로필-2,5-디옥소-3-(4-(4-니트로페닐설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-63)(3S)-1-프로필-2,5-디옥소-3-(4-(4-(메틸설포닐)페닐설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 20A-10]
실시예 번호
화합물명
22(H20-64)(3S)-1-프로필-2,5-디옥소-3-(4-(4-트리플루오로메틸페닐설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-65)(3S)-1-프로필-2,5-디옥소-3-(4-(4-페닐페닐설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-66)(3S)-1-프로필-2,5-디옥소-3-(4-(2-페닐페닐설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-67)(3S)-1-프로필-2,5-디옥소-3-(4-(3,4-디플루오로페닐설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-68)(3S)-1-프로필-2,5-디옥소-3-(4-(2,6-디플루오로페닐설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-69)(3S)-1-프로필-2,5-디옥소-3-(4-(2,5-디플루오로페닐설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-70)(3S)-1-프로필-2,5-디옥소-3-(4-(2,5-디메톡시페닐설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 20A-11]
실시예 번호
화합물명
22(H20-71)(3S)-1-프로필-2,5-디옥소-3-(4-(2-클로로-4-트리플루오로메틸페닐설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-72)(3S)-1-프로필-2,5-디옥소-3-(4-(2-나프틸설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-73)(3S)-1-프로필-2,5-디옥소-3-(4-((1E)-2-페닐비닐설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-74)(3S)-1-프로필-2,5-디옥소-3-(4-(푸란-2-일설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H20-75)(3S)-1-프로필-2,5-디옥소-3-(4-(티오펜-2-일설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 21A-1]
실시예 번호
화합물명
22(H21-1)(3S)-1-프로필-2,5-디옥소-3-(4-(4-브로모-2,5-디클로로티오펜-3-일설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-2)(3S)-1-프로필-2,5-디옥소-3-(4-(5-페닐설포닐티오펜-2-일설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-3)(3S)-1-프로필-2,5-디옥소-3-(4-(7-클로로벤조프라잔-4-일설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-4)(3S)-1-프로필-2,5-디옥소-3-(4-(4-메틸-2-아세틸아미노티아졸-5-일설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-5)(3S)-1-프로필-2,5-디옥소-3-(4-(2-메톡시-디벤조푸란-3-일설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-6)(3S)-1-프로필-2,5-디옥소-3-(4-(3,4-디클로로페닐설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-7)(3S)-1-프로필-2,5-디옥소-3-(4-(4-메톡시페닐설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 21A-2]
실시예 번호
화합물명
22(H21-8)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질설포닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-9)(3S)-1-프로필-2,5-디옥소-3-(4-((에틸아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-10)(3S)-1-프로필-2,5-디옥소-3-(4-((프로필아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-11)(3S)-1-프로필-2,5-디옥소-3-(4-((1-메틸에틸아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-12)(3S)-1-프로필-2,5-디옥소-3-(4-((부틸아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-13)(3S)-1-프로필-2,5-디옥소-3-(4-((4-클로로페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-14)(3S)-1-프로필-2,5-디옥소-3-(4-((페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 21A-3]
실시예 번호
화합물명
22(H21-15)(3S)-1-프로필-2,5-디옥소-3-(4-((4-메틸페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-16)(3S)-1-프로필-2,5-디옥소-3-(4-((헥실아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-17)(3S)-1-프로필-2,5-디옥소-3-(4-((4-플루오로페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-18)(3S)-1-프로필-2,5-디옥소-3-(4-((벤질아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-19)(3S)-1-프로필-2,5-디옥소-3-(4-((시클로헥실아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-20)(3S)-1-프로필-2,5-디옥소-3-(4-((3-메틸페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-21)(3S)-1-프로필-2,5-디옥소-3-(4-((옥틸아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 21A-4]
실시예 번호
화합물명
22(H21-22)(3S)-1-프로필-2,5-디옥소-3-(4-((4-브로모페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-23)(3S)-1-프로필-2,5-디옥소-3-(4-((2-(티오펜-2-일)에틸아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-24)(3S)-1-프로필-2,5-디옥소-3-(4-((4-(1-메틸에틸)페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-25)(3S)-1-프로필-2,5-디옥소-3-(4-((3-클로로페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-26)(3S)-1-프로필-2,5-디옥소-3-(4-((2,4,5-트리메틸페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-27)(3S)-1-프로필-2,5-디옥소-3-(4-((2,4,6-트리메틸페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-28)(3S)-1-프로필-2,5-디옥소-3-(4-((4-페닐옥시페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 21A-5]
실시예 번호
화합물명
22(H21-29)(3S)-1-프로필-2,5-디옥소-3-(4-((4-부틸옥시페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-30)(3S)-1-프로필-2,5-디옥소-3-(4-((4-페닐페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-31)(3S)-1-프로필-2,5-디옥소-3-(4-((2-페닐페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-32)(3S)-1-프로필-2,5-디옥소-3-(4-((4-트리플루오로메틸페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-33)(3S)-1-프로필-2,5-디옥소-3-(4-((3,4-디클로로페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-34)(3S)-1-프로필-2,5-디옥소-3-(4-((4-부틸옥시카르보닐페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-35)(3S)-1-프로필-2,5-디옥소-3-(4-((2,6-비스(1-메틸에틸)페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 21A-6]
실시예 번호
화합물명
22(H21-36)(3S)-1-프로필-2,5-디옥소-3-(4-((2,5-디메틸페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-37)(3S)-1-프로필-2,5-디옥소-3-(4-((2-에틸-6-(1-메틸에틸)페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-38)(3S)-1-프로필-2,5-디옥소-3-(4-((2,4,6-트리클로로페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-39)(3S)-1-프로필-2,5-디옥소-3-(4-((3,4-디메틸페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-40)(3S)-1-프로필-2,5-디옥소-3-(4-((2-메틸티오페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-41)(3S)-1-프로필-2,5-디옥소-3-(4-((4-메틸티오페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-42)(3S)-1-프로필-2,5-디옥소-3-(4-((4-부틸페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 21A-7]
실시예 번호
화합물명
22(H21-43)(3S)-1-프로필-2,5-디옥소-3-(4-((2-클로로-5-트리플루오로메틸페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-44)(3S)-1-프로필-2,5-디옥소-3-(4-((2,6-디브로모-4-에틸페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-45)(3S)-1-프로필-2,5-디옥소-3-(4-((1-에톡시카르보닐-2-메틸프로필아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-46)(3S)-1-프로필-2,5-디옥소-3-(4-((페닐카르보닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-47)(3S)-1-프로필-2,5-디옥소-3-(4-((2,4,6-트리브로모페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-48)(3S)-1-프로필-2,5-디옥소-3-(4-((2,5-디플루오로페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-49)(3S)-1-프로필-2,5-디옥소-3-(4-((3,5-비스(메톡시카르보닐)페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 21A-8]
실시예 번호
화합물명
22(H21-50)(3S)-1-프로필-2,5-디옥소-3-(4-((6,7-메틸렌디옥시쿠마린-4-일메틸아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-51)(3S)-1-프로필-2,5-디옥소-3-(4-((2,6-디메틸페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-52)(3S)-1-프로필-2,5-디옥소-3-(4-((2-메틸프로필옥시)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-53)(3S)-1-프로필-2,5-디옥소-3-(4-((2-에틸헥실옥시)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-54)(3S)-1-프로필-2,5-디옥소-3-(4-(에톡시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-55)(3S)-1-프로필-2,5-디옥소-3-(4-(알릴옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-56)(3S)-1-프로필-2,5-디옥소-3-(4-(프로필옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 21A-9]
실시예 번호
화합물명
22(H21-57)(3S)-1-프로필-2,5-디옥소-3-(4-(부틸옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-58)(3S)-1-프로필-2,5-디옥소-3-(4-(헥실옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-59)(3S)-1-프로필-2,5-디옥소-3-(4-((2,2,2-트리클로로에틸옥시)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-60)(3S)-1-프로필-2,5-디옥소-3-(4-((플루오렌-9-일메틸옥시)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-61)(3S)-1-프로필-2,5-디옥소-3-(4-((1S,5S,2R)-5-메틸-2-(1-메틸에틸)시클로헥실옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-62)(3S)-1-프로필-2,5-디옥소-3-(4-((2-메톡시에톡시)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-63)(3S)-1-프로필-2,5-디옥소-3-(4-(펜틸옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 21A-10]
실시예 번호
화합물명
22(H21-64)(3S)-1-프로필-2,5-디옥소-3-(4-((1-메틸에틸옥시)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-65)(3S)-1-프로필-2,5-디옥소-3-(4-((3-부테닐옥시)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-66)(3S)-1-프로필-2,5-디옥소-3-(4-((2S,1R,5R)-메틸-2-(1-메틸에틸)시클로헥실옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-67)(3S)-1-프로필-2,5-디옥소-3-(4-(시클로펜틸옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-68)(3S)-1-프로필-2,5-디옥소-3-(4-((1,1-디메틸에틸옥시)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-69)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-70)(3S)-1-프로필-2,5-디옥소-3-(4-((N,N-디페닐아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 21A-11]
실시예 번호
화합물명
22(H21-71)(3S)-1-프로필-2,5-디옥소-3-(4-((N-페닐-N-메틸아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-72)(3S)-1-프로필-2,5-디옥소-3-(4-((N,N-디메틸아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-73)(3S)-1-프로필-2,5-디옥소-3-(4-((N,N-디에틸아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-74)(3S)-1-프로필-2,5-디옥소-3-(4-((N,N-비스(1-메틸에틸)아미노)카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-75)(3S)-1-프로필-2,5-디옥소-3-(4-(모르폴린-4-일카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-76)(3S)-1-프로필-2,5-디옥소-3-(4-(카르바졸-9-일카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
22(H21-77)(3S)-1-프로필-2,5-디옥소-3-(4-(피롤리딘-1-일카르보닐아미노)부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 20B-1]
[표 20B-2]
[표 20B-3]
[표 20B-4]
[표 20B-5]
[표 20B-6]
[표 20B-7]
[표 20B-8]
[표 20B-9]
[표 20B-10]
[표 20B-11]
[표 20B-12]
[표 21B-1]
[표 21B-2]
[표 21B-3]
[표 21B-4]
[표 21B-5]
[표 21B-6]
[표 21B-7]
[표 21B-8]
[표 21B-9]
[표 21B-10]
[표 21B-11]
[표 21B-12]
[표 20C-1]
[표 20C-2]
[표 20C-3]
[표 21C-1]
[표 21C-2]
[표 21C-3]
실시예 23
1-시클로프로필메틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-페녹시페닐)-1,3,9-트리아자스피로[5.5]운데칸·초산염
참고예 2에서 제조한 수지(3)(0.5 g)의 테트라히드로푸란/메탄올(1:1; 5 ml)의 현탁액에 N-알릴옥시카르보닐-4-피페리돈(0.396 g), 시클로프로필메틸아민(0.189 ml) 및 N-(t-부틸옥시카르보닐)류신(0.542 g)을 첨가하여 65℃에서 18시간 교반하였다. 반응 용액을 실온에서 냉각시키고, 수지를 여과하여 취하였다. 얻어진 수지를 디메틸포름아미드(5 ml×2회), 염화메틸렌(5 ml×2회), 메탄올(5 ml×2회) 및 염화메틸렌(5 ml×2회)으로 세정하였다. 얻어진 수지의 염화메틸렌(5 ml) 현탁액에 초산(0.149 ml), 수소화트리부틸주석(0.351 ml) 및 테트라키스트리페닐포스핀팔라듐(0) 착물(50 mg)를 첨가하여 실온에서 6시간 교반하였다. 반응 용액으로부터 수지를 여과하여 취하고, 염화메틸렌(5 ml×4회) 및 디메틸포름아미드(5 ml×3회)로 세정하였다. 얻어진 수지 1% 초산-디메틸포름아미드 용액(5 ml)에 현탁하고, 거기에 4-페닐옥시벤조알데히드(0.252 g), 트리아세톡시수소화붕소나트륨(0.277 g)을 첨가하여 실온에서 15시간 교반하였다. 반응 용액으로부터 수지를 여과하여 취하고, 메탄올(5 ml×1회), 디메틸포름아미드(5 ml×3회), 메탄올(5 ml×4회) 및 염화메틸렌(5 ml×4회)으로 세정하였다. 얻어진 수지를 50% 트리플루오로초산-염화메틸렌(5 ml) 용액에 현탁하고 실온에서 5분간 교반하였다. 반응 용액을 여과하고, 얻어진 수지를 재차 50% 트리플루오로초산-염화메틸렌 용액(5 ml)에 현탁하고 실온에서 30분간 교반하였다. 반응 용액으로부터의 여과하여 취한 수지를 염화메틸렌(5 ml×3회), 1.25 M 초산-톨루엔 용액(5 ml×3회)으로 세정하였다. 얻어진 수지를 1.25 M 초산-톨루엔 용액(5 ml)에 현탁하고 90℃에서 23시간 교반하였다. 반응 용액을 여과하고, 얻어진 수지를 클로로포름-메탄올(1:1; 2 ml×2회)로 세정하였다. 여과액과 세정액을 농축하여 이하의 물성치를 갖는 본 발명 화합물(274 mg)을 얻었다.
TLC: Rf 0.40(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.49(m, 2H), 7.40(m, 2H), 7.18(m, 2H), 7.04(m, 3H), 4.33(s, 2H), 4.04(dd, J=8.1, 4.8Hz, 1H), 3.78(m, 2H), 3.52(m, 2H), 3.35(m, 2H), 2.45-2.10(m, 4H), 1.98(s, 3H, CH3COOH), 1.97-1.58(m, 4H), 0.94(d, J=6.0Hz, 6H), 0.51(m, 2H), 0.36(m, 2H).
실시예 23(1)
1-(티오펜-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페녹시페닐)-1,3,9-트리아자스피로[5.5]운데칸 초산염
참고예 2에서 제조한 수지(3)(0.5 g), N-알릴옥시카르보닐-4-피페리돈(0.396g), 티오펜-2-일메틸아민(0.205 ml) 및 N-(t-부틸옥시카르보닐)류신(0.542 g), 4-페닐옥시벤조알데히드(0.252 g)를 이용하여 실시예 23과 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물(274 mg)을 얻었다.
TLC: Rf 0.39(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.48(m, 2H), 7.39(m, 2H), 7.28(m, 1H), 7.18(m, 2H), 7.04(m, 4H), 6.91(m, 1H), 4.86(s, 2H), 4.32(s, 2H), 4.12(dd, J=8.1, 4.5Hz, 1H), 3.77(m, 2H), 3.49(m, 2H), 2.60-2.30(m, 2H), 2.19(m, 2H), 1.98(s, 3H), 1.97-1.58(m, 3H), 0.94(d, J=6.0Hz, 6H).
실시예 23(H22-1)∼23(H31-31)
참고예 2에서 제조한 수지(3), 해당하는 4-피페리돈 유도체, 해당하는 아민 유도체, 해당하는 아미노산 유도체 및 해당하는 알데히드 유도체를 이용하여 실시예 23 또는 23(1)과 동일한 조작을 하여 이하의 표 22A-1∼31A-4에 화합물명을 나타내고 표 22B-1∼31B-5에 구조식을 나타낸 본 발명 화합물을 얻었다. 또한, 이들의 본 발명 화합물의 물성치를 이하의 표 22C-1∼31C-2에 나타내었다.
[표 22A-1]
실시예 번호
화합물명
23(H22-1)(3S)-1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-2)(3R)-1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-3)(3S)-1-프로필-2,5-디옥소-3-메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-4)(3S)-1-프로필-2,5-디옥소-3-벤질-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-5)(3S)-1-프로필-2,5-디옥소-3-(1-(벤질옥시메틸)이미다졸-5-일메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-6)(3S)-1-프로필-2,5-디옥소-3-(벤질옥시메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-7)(3S)-1-프로필-2,5-디옥소-3-(4-메톡시페닐메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-8)(3S)-1-프로필-2,5-디옥소-3-((1R)-1-(벤질옥시)에틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
[표 22A-2]
실시예 번호
화합물명
23(H22-9)(3S)-1-프로필-2,5-디옥소-3-(피리딘-3-일메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-10)(3S)-1-프로필-2,5-디옥소-3-부틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-11)(3S)-1-프로필-2,5-디옥소-3-(시클로헥실옥시카르보닐메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-12)(3S)-1-프로필-2,5-디옥소-3-(시클로헥실메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-13)(3R)-1-프로필-2,5-디옥소-3-(시클로헥실옥시카르보닐메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-14)(3R)-1-프로필-2,5-디옥소-3-(2-(시클로헥실옥시카르보닐)에틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-15)(3R)-1-프로필-2,5-디옥소-3-(4-(벤질옥시)페닐메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-16)(3S)-1-프로필-2,5-디옥소-3-히드록시메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
[표 22A-3]
실시예 번호
화합물명
23(H22-17)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시)페닐메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-18)(3R)-1-프로필-2,5-디옥소-3-부틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-19)(3R)-1-프로필-2,5-디옥소-3-(시클로헥실메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-20)(3R)-1-프로필-2,5-디옥소-3-((1S)-1-(벤질옥시)에틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-21)(3R)-1-프로필-2,5-디옥소-3-(벤질옥시메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-22)(3R)-1-프로필-2,5-디옥소-3-((4-메톡시페닐메틸티오)메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-23)(3R)-1-프로필-2,5-디옥소-3-(벤질티오메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-24)(3S)-1-프로필-2,5-디옥소-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
[표 22A-4]
실시예 번호
화합물명
23(H22-25)(3S)-1-프로필-2,5-디옥소-3-(이미다졸-4-일메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-26)(3S)-1-프로필-2,5-디옥소-3-히드록시메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-27)(3R)-1-프로필-2,5-디옥소-3-((3-니트로피리딘-2-일)디설파닐메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-28)(3S)-1-프로필-2,5-디옥소-3-(1-벤질이미다졸-4-일메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-29)(3R)-1-프로필-2,5-디옥소-3-(4-히드록시페닐메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-30)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)페닐메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-31)(3R)-1-프로필-2,5-디옥소-3-(3-(아미노카르보닐아미노)프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-32)(3R)-1-프로필-2,5-디옥소-3-(1-나프틸메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
[표 22A-5]
실시예 번호
화합물명
23(H22-33)(3S)-1-프로필-2,5-디옥소-3-(3,4-디클로로페닐메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-34)(3R)-1-프로필-2,5-디옥소-3-((1,1-디메틸에틸티오)메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-35)(3S)-1-프로필-2,5-디옥소-3-(2-메틸프로필)-4-메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-36)(3S)-1-프로필-2,5-디옥소-3-프로필-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-37)(3S)-1-프로필-2,5-디옥소-3-(4-벤질옥시페닐메틸)-4-메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-38)(3S)-1-프로필-2,5-디옥소-3-((1R)-1-히드록시에틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-39)(3S)-1-프로필-2,5-디옥소-3-(아미노카르보닐메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-40)(3S)-1-프로필-2,5-디옥소-3-((1R)-1-히드록시에틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-41)(3R)-1-프로필-2,5-디옥소-3-메틸-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
[표 22A-6]
실시예 번호
화합물명
23(H22-42)(3R)-1-프로필-2,5-디옥소-3-(피리딘-3-일메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-43)(3S)-1-프로필-2,5-디옥소-3-(카르복시메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-44)(3S)-1-프로필-2,5-디옥소-3-(4-히드록시페닐메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-45)(3S)-1-프로필-2,5-디옥소-3-(2-메틸티오에틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-46)(3R)-1-프로필-2,5-디옥소-3-((메틸카르보닐아미노)메틸티오메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-47)(3R)-1-프로필-2,5-디옥소-3-((1S)-1-히드록시에틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-48)(3S)-1-프로필-2,5-디옥소-3-(2-클로로페닐메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-49)(3S)-1-프로필-2,5-디옥소-3-(1-나프틸메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-50)(3S)-1-프로필-2,5-디옥소-3-(4-플루오로페닐메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
[표 22A-7]
실시예 번호
화합물명
23(H22-51)(3S)-1-프로필-2,5-디옥소-3-(시아노메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-52)(3R)-1-프로필-2,5-디옥소-3-(인돌-3-일메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-53)(3S)-1-프로필-2,5-디옥소-3-(4-(2-클로로페닐메틸옥시카르보닐아미노)부틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-54)(3R)-1-프로필-2,5-디옥소-3-(벤질옥시카르보닐메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-55)(3S)-1-프로필-2,5-디옥소-3-(3-(1-이미노-1-(2,4,6-트리메틸페닐설포닐아미노)메틸아미노)프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-56)(3S)-1-프로필-2,5-디옥소-3-(벤질옥시카르보닐메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-57)(3S)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-58)(3R)-1-프로필-2,5-디옥소-3-(4-메톡시페닐메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
[표 22A-8]
실시예 번호
화합물명
23(H22-59)(3R)-1-프로필-2,5-디옥소-3-(4-(벤질옥시카르보닐아미노)부틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-60)(3S)-1-프로필-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-61)(3R)-1-프로필-2,5-디옥소-3-(1-(벤질옥시메틸)이미다졸-4-일메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-62)(3R)-1-프로필-2,5-디옥소-3-(4-에톡시페닐메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-63)(3S)-1-프로필-2,5-디옥소-3-(4-페닐페닐메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
23(H22-64)(3S)-1-프로필-2,5-디옥소-3-(1,1-디페닐메틸)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸
[표 23A-1]
실시예 번호
화합물명
23(H23-1)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H23-2)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H23-3)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-디에틸아미노페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H23-4)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H23-5)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-벤질옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H23-6)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H23-7)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-알릴옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H23-8)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(디벤조푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H23-9)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐이미다졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 23A-2]
실시예 번호
화합물명
23(H23-10)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H23-11)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H23-12)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-디에틸아미노페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H23-13)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H23-14)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-벤질옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H23-15)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H23-16)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-알릴옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H23-17)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(디벤조푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H23-18)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-페닐이미다졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 24A-1]
실시예 번호
화합물명
23(H24-1)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-2)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-3)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-메틸푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-4)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-브로모티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-5)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(3-메틸티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-6)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-에틸푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-7)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(피리딘-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-8)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(1-메틸인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-9)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-메틸이미다졸-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 24A-2]
실시예 번호
화합물명
23(H24-10)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(2,4-디옥소-1,3-디히드로피리미딘-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-11)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(2-클로로페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-12)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(3-클로로페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-13)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-14)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(히드록시메틸)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-15)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(카르복시)티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-16)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(카르복시)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-17)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-에틸티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-18)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(1-메틸벤조이미다졸-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 24A-3]
실시예 번호
화합물명
23(H24-19)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(2-트리플루오로메톡시페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-20)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(6-(메톡시카르보닐)인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-21)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(2,6-디클로로-4-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-22)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-브로모티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-23)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(2-클로로-5-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-24)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(3-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-25)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(1-아세틸인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 24A-4]
실시예 번호
화합물명
23(H24-26)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(3,5-비스(트리플루오로메틸)페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-27)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-클로로-3-메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-28)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(4-메톡시페닐)티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-29)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(2-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-30)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(2,5-디메틸-1-(4-카르복시페닐)피롤-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H24-31)1-에틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(4-클로로페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.6]운데칸
[표 25A-1]
실시예 번호
화합물명
23(H25-1)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H25-2)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H25-3)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(5-메틸푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H25-4)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(5-브로모티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H25-5)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(3-메틸티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H25-6)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(5-에틸푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H25-7)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(1-메틸인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H25-8)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-메틸이미다졸-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 25A-2]
실시예 번호
화합물명
23(H25-9)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2,4-디옥소-1,3-디히드로피리미딘-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H25-10)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(5-(2-클로로페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H25-11)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H25-12)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(5-(히드록시메틸)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H25-13)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(5-(카르복시)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H25-14)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(5-에틸티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H25-15)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(1-메틸벤조이미다졸-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H25-16)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(5-(2-트리플루오로메톡시페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 25A-3]
실시예 번호
화합물명
23(H25-17)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(6-(메톡시카르보닐)인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H25-18)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(5-(2,6-디클로로-4-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H25-19)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-브로모티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H25-20)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(5-(2-클로로-5-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H25-21)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(5-(3-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H25-22)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(1-아세틸인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H25-23)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(5-(3,5-비스(트리플루오로메틸)페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 25A-4]
실시예 번호
화합물명
23(H25-24)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(5-클로로-3-메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H25-25)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(5-(4-메톡시페닐)티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H25-26)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(5-(2-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H25-27)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(2,5-디메틸-1-(4-카르복시페닐)피롤-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H25-28)1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(5-(4-클로로페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.6]운데칸
[표 26A-1]
실시예 번호
화합물명
23(H26-1)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-2)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-3)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-메틸푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-4)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-브로모티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-5)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3-메틸티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-6)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-에틸푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-7)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(피리딘-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-8)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(1-메틸인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-9)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-메틸이미다졸-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 26A-2]
실시예 번호
화합물명
23(H26-10)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2,4-디옥소-1,3-디히드로피리미딘-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-11)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(2-클로로페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-12)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(3-클로로페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-13)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-14)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(히드록시메틸)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-15)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(카르복시)티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-16)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(카르복시)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-17)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-에틸티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-18)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(1-메틸벤조이미다졸-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 26A-3]
실시예 번호
화합물명
23(H26-19)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(2-트리플루오로메톡시페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-20)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(6-(메톡시카르보닐)인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-21)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(2,6-디클로로-4-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-22)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-브로모티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-23)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(2-클로로-5-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-24)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(3-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-25)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(1-아세틸인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 26A-4]
실시예 번호
화합물명
23(H26-26)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(3,5-비스(트리플루오로메틸)페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-27)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-클로로-3-메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-28)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(4-메톡시페닐)티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-29)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(2-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-30)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2,5-디메틸-1-(4-카르복시페닐)피롤-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H26-31)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(4-클로로페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.6]운데칸
[표 27A-1]
실시예 번호
화합물명
23(H27-1)1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
23(H27-2)1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-((4-메톡시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-3)1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-4)1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-((4-페녹시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-5)1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-((4-벤질옥시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-6)1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-7)1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐이미다졸-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-8)1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-((4-히드록시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-9)1-((2-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
[표 27A-2]
실시예 번호
화합물명
23(H27-10)1-((2-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-메톡시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-11)1-((2-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-12)1-((2-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-페녹시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-13)1-((2-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-벤질옥시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-14)1-((2-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-15)1-((2-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐이미다졸-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-16)1-((2-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-히드록시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 27A-3]
실시예 번호
화합물명
23(H27-17)1-((3-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
23(H27-18)1-((3-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-메톡시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-19)1-((3-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-페녹시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-20)1-((3-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-벤질옥시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-21)1-((3-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-22)1-((3-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐이미다졸-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-23)1-((3-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-히드록시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 27A-4]
실시예 번호
화합물명
23(H27-24)1-((4-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
23(H27-25)1-((4-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-26)1-((4-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-페녹시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-27)1-((4-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-벤질옥시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-28)1-((4-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-29)1-((4-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐이미다졸-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-30)1-((4-메톡시페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-히드록시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 27A-5]
실시예 번호
화합물명
23(H27-31)1-(피리딘-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
23(H27-32)1-(피리딘-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-메톡시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-33)1-(피리딘-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(2H,3H-벤조[3,4-e]1,4-디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-34)1-(피리딘-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-페녹시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-35)1-(피리딘-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-벤질옥시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-36)1-(피리딘-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-37)1-(피리딘-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐이미다졸-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 27A-6]
실시예 번호
화합물명
23(H27-38)1-(피리딘-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-히드록시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-39)1-(피리딘-3-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
23(H27-40)1-(피리딘-3-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-메톡시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-41)1-(피리딘-3-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-42)1-(피리딘-3-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-페녹시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-43)1-(피리딘-3-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-벤질옥시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-44)1-(피리딘-3-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 27A-7]
실시예 번호
화합물명
23(H27-45)1-(피리딘-3-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐이미다졸-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-46)1-(피리딘-3-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-히드록시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-47)1-(피리딘-4-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
23(H27-48)1-(피리딘-4-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-메톡시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-49)1-(피리딘-4-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-50)1-(피리딘-4-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-페녹시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-51)1-(피리딘-4-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-벤질옥시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 27A-8]
실시예 번호
화합물명
23(H27-52)1-(피리딘-4-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-53)1-(피리딘-4-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐이미다졸-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-54)1-(피리딘-4-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-히드록시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-55)1-((2-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
23(H27-56)1-((2-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-메톡시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-57)1-((2-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-58)1-((2-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-페녹시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 27A-9]
실시예 번호
화합물명
23(H27-59)1-((2-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-벤질옥시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-60)1-((2-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-61)1-((2-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐이미다졸-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-62)1-((2-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-히드록시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-63)1-((3-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
23(H27-64)1-((3-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-메톡시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-65)1-((3-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 27A-10]
실시예 번호
화합물명
23(H27-66)1-((3-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-페녹시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-67)1-((3-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-벤질옥시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-68)1-((3-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-69)1-((3-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐이미다졸-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-70)1-((3-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-히드록시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-71)1-((4-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
23(H27-72)1-((4-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-메톡시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 27A-11]
실시예 번호
화합물명
23(H27-73)1-((4-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-74)1-((4-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-페녹시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-75)1-((4-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-벤질옥시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-76)1-((4-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-77)1-((4-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐이미다졸-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H27-78)1-((4-메틸페닐)메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((4-히드록시페닐)메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 28A-1]
실시예 번호
화합물명
23(H28-1)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-2)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-3)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(5-메틸푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-4)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(5-브로모티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-5)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(3-메틸티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-6)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(5-에틸푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-7)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(피리딘-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-8)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(1-메틸인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-9)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(4-메틸이미다졸-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 28A-2]
실시예 번호
화합물명
23(H28-10)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(2,4-디옥소-1,3-디히드로피리미딘-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-11)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(5-(2-클로로페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-12)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(5-(3-클로로페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-13)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(5-(히드록시메틸)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-14)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(5-(카르복시)티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-15)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(5-(카르복시)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-16)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(5-에틸티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-17)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(1-메틸벤조이미다졸-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 28A-3]
실시예 번호
화합물명
23(H28-18)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(5-(2-트리플루오로메톡시페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-19)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(6-(메톡시카르보닐)인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-20)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(5-(2,6-디클로로-4-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-21)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(4-브로모티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-22)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(5-(2-클로로-5-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-23)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(5-(3-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-24)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(1-아세틸인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 28A-4]
실시예 번호
화합물명
23(H28-25)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(5-(3,5-비스(트리플루오로메틸)페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-26)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(5-클로로-3-메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-27)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(5-(4-메톡시페닐)티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-28)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(5-(2-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-29)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(2,5-디메틸-1-(4-카르복시페닐)피롤-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H28-30)1-프로필-2,5-디옥소-3-시클로헥실메틸-9-(5-(4-클로로페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.6]운데칸
[표 29A-1]
실시예 번호
화합물명
23(H29-1)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-2)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-3)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-메틸푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-4)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-브로모티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-5)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3-메틸티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-6)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-에틸푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-7)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(피리딘-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-8)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(1-메틸인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-9)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-메틸이미다졸-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 29A-2]
실시예 번호
화합물명
23(H29-10)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2,4-디옥소-1,3-디히드로피리미딘-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-11)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-(2-클로로페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-12)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-(3-클로로페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-13)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-14)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-(히드록시메틸)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-15)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-(카르복시)티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-16)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-(카르복시)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-17)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-에틸티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-18)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(1-메틸벤조이미다졸-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 29A-3]
실시예 번호
화합물명
23(H29-19)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-(2-트리플루오로메톡시페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-20)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(6-(메톡시카르보닐)인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-21)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-(2,6-디클로로-4-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-22)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-브로모티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-23)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-(2-클로로-5-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-24)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-(3-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-25)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(1-아세틸인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 29A-4]
실시예 번호
화합물명
23(H29-26)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-(3,5-비스(트리플루오로메틸)페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-27)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-클로로-3-메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-28)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-(4-메톡시페닐)티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-29)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-(2-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-30)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2,5-디메틸-1-(4-카르복시페닐)피롤-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H29-31)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-(4-클로로페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.6]운데칸
[표 30A-1]
실시예 번호
화합물명
23(H30-1)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-2)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-3)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(5-메틸푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-4)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(5-브로모티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-5)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(3-메틸티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-6)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(5-에틸푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-7)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(피리딘-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-8)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(1-메틸인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 30A-2]
실시예 번호
화합물명
23(H30-9)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(4-메틸이미다졸-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-10)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(2,4-디옥소-1,3-디히드로피리미딘-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-11)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(5-(2-클로로페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-12)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(5-(3-클로로페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-13)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-14)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(5-(히드록시메틸)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-15)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(5-(카르복시)티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 30A-3]
실시예 번호
화합물명
23(H30-16)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(5-(카르복시)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-17)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(5-에틸티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-18)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(1-메틸벤조이미다졸-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-19)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(5-(2-트리플루오로메톡시페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-20)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(6-(메톡시카르보닐)인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-21)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(5-(2,6-디클로로-4-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-22)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(4-브로모티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 30A-4]
실시예 번호
화합물명
23(H30-23)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(5-(2-클로로-5-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-24)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(5-(3-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-25)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(1-아세틸인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-26)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(5-(3,5-비스(트리플루오로메틸)페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-27)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(5-클로로-3-메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-28)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(5-(4-메톡시페닐)티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-29)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(5-(2-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 30A-5]
실시예 번호
화합물명
23(H30-30)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(2,5-디메틸-1-(4-카르복시페닐)피롤-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H30-31)1-(2-메톡시에틸)-2,5-디옥소-3-시클로헥실메틸-9-(5-(4-클로로페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.6]운데칸
[표 31A-1]
실시예 번호
화합물명
23(H31-1)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-2)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-3)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(5-메틸푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-4)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(5-브로모티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-5)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(3-메틸티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-6)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(5-에틸푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-7)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(피리딘-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-8)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(1-메틸인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-9)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(4-메틸이미다졸-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 31A-2]
실시예 번호
화합물명
23(H31-10)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(2,4-디옥소-1,3-디히드로피리미딘-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-11)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(5-(2-클로로페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-12)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(5-(3-클로로페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-13)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-14)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(5-(히드록시메틸)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-15)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(5-(카르복시)티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-16)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(5-(카르복시)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-17)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(5-에틸티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-18)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(1-메틸벤조이미다졸-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 31A-3]
실시예 번호
화합물명
23(H31-19)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(5-(2-트리플루오로메톡시페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-20)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(6-(메톡시카르보닐)인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-21)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(5-(2,6-디클로로-4-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-22)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(4-브로모티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-23)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(5-(2-클로로-5-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-24)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(5-(3-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-25)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(1-아세틸인돌-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 31A-4]
실시예 번호
화합물명
23(H31-26)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(5-(3,5-비스(트리플루오로메틸)페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-27)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(5-클로로-3-메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-28)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(5-(4-메톡시페닐)티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-29)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(5-(2-트리플루오로메틸페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-30)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(2,5-디메틸-1-(4-카르복시페닐)피롤-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
23(H31-31)1-벤질-2,5-디옥소-3-시클로헥실메틸-9-(5-(4-클로로페닐)푸란-2-일메틸)-1,4,9-트리아자스피로[5.6]운데칸
[표 22B-1]
[표 22B-2]
[표 22B-3]
[표 22B-4]
[표 22B-5]
[표 22B-6]
[표 22B-7]
[표 22B-8]
[표 22B-9]
[표 23B-1]
[표 23B-2]
[표 23B-3]
[표 24B-1]
[표 24B-2]
[표 24B-3]
[표 24B-4]
[표 24B-5]
[표 25B-1]
[표 25B-2]
[표 25B-3]
[표 25B-4]
[표 25B-5]
[표 26B-1]
[표 26B-2]
[표 26B-3]
[표 26B-4]
[표 26B-5]
[표 27B-1]
[표 27B-2]
[표 27B-3]
[표 27B-4]
[표 27B-5]
[표 27B-6]
[표 27B-7]
[표 27B-8]
[표 27B-9]
[표 27B-10]
[표 27B-11]
[표 28B-1]
[표 28B-2]
[표 28B-3]
[표 28B-4]
[표 28B-5]
[표 29B-1]
[표 29B-2]
[표 29B-3]
[표 29B-4]
[표 29B-5]
[표 30B-1]
[표 30B-2]
[표 30B-3]
[표 30B-4]
[표 30B-5]
[표 31B-1]
[표 31B-2]
[표 31B-3]
[표 31B-4]
[표 31B-5]
[표 22C-1]
[표 22C-2]
[표 22C-3]
[표 23C]
[표 24C-1]
[표 24C-2]
[표 25C-1]
[표 25C-2]
[표 26C-1]
[표 26C-2]
[표 27C-1]
[표 27C-2]
[표 27C-3]
[표 28C-1]
[표 28C-2]
[표 29C-1]
[표 29C-2]
[표 30C-1]
[표 30C-2]
[표 31C-1]
[표 31C-2]
실시예 24(1)∼24(119)
참고예 2에서 제조한 수지(3) 및 N-알릴옥시카르보닐-4-피페리돈과, n-프로필아민 및 N-(t-부틸옥시카르보닐)류신 대신에 각각 해당하는 화합물을 이용하여 참고예 3→참고예 4와 동일한 조작을 하고, 또한 3,5-디메틸-1-페닐-4-포르밀피라졸 대신에 해당하는 화합물을 이용하여 참고예 5→참고예 6→실시예 1과 동일한 조작을 하여 이하의 본 발명 화합물을 얻었다.
실시예 24(1)
(3S)-1-부틸-2,5-디옥소-3-(4-메톡시페닐메틸)-9-시클로헥실메틸-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.44(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.06(d, J=9.0Hz, 2H), 6.84(d, J=9.0Hz, 2H), 4.31(dd, J=4.5, 3.6Hz, 1H), 3.82-3.67(m, 4H), 3.49-3.30(m, 3H), 3.25(dd, J=13.8, 3.6Hz, 1H), 3.23-3.10(m, 2H), 2.95-2.87(m, 2H), 2.87(dd, J=13.8, 4.5Hz, 1H), 2.31(m, 1H), 2.05(m, 1H), 1.91-1.64(m, 7H), 1.56-1.14(m, 7H), 1.09-0.91(m, 5H), 0.26(m, 1H).
실시예 24(2)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-(4-클로로페닐)티오펜-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.60(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.65(d, J=8.7Hz, 2H), 7.42(d, J=8.7Hz, 2H), 7.42(d, J=3.6Hz, 1H), 7.34(d, J=3.6Hz, 1H), 4.61(brs, 2H), 4.01(dd, J=7.8, 4.5Hz, 1H), 3.95-3.72(m, 2H), 3.65-3.50(m, 2H), 3.44-3.34(m, 2H), 2.50-2.12(m, 4H), 1.89-1.45(m, 5H), 1.45-1.28(m, 2H), 1.13-0.89(m, 9H).
실시예 24(3)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-(4-메톡시페닐)티오펜-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.60(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.57(d, J=9.0Hz, 2H), 7.33-7.26(m, 2H), 6.97(d, J=9.0Hz, 2H), 4.58(brs, 2H), 4.01(dd, J=7.5, 4.5Hz, 1H), 3.93-3.71(m, 5H), 3.64-3.50(m, 2H), 3.44-3.34(m, 2H), 2.49-2.12(m, 4H), 1.90-1.45(m, 5H), 1.45-1.28(m, 2H), 1.03-0.88(m, 9H).
실시예 24(4)
1-((2E)-2-부테닐)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.32(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.52(d, J=8.7Hz, 2H), 7.44-7.35(m, 2H), 7.22-7.14(m, 1H), 7.06(d, J=8.7Hz, 2H), 7.10-7.00(m, 2H), 5.75-5.60(m, 1H), 5.52-5.38(m, 1H), 4.33(s, 2H), 4.15-3.93(m, 2H), 4.03(dd, J=7.8, 4.5Hz, 1H), 3.88-3.66(m, 2H), 3.55-3.42(m, 2H), 2.52-2.35(m, 2H), 2.28-2.08(m, 2H), 1.90-1.57(m, 3H), 1.65(dd, J=6.3, 1.5Hz, 3H), 0.95(d, J=6.6Hz, 3H), 0.94(d, J=6.6Hz, 3H).
실시예 24(5)
1-(푸란-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.33(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.52(d, J=8.7Hz, 2H), 7.43-7.36(m, 3H), 7.18(t, J=7.2Hz, 1H), 7.09-6.99(m, 4H), 6.33(m, 1H), 6.28(d, J=3.0Hz, 1H), 4.69(s, 2H), 4.33(s, 2H), 4.08(dd, J=7.8, 4.5Hz, 1H), 3.87-3.72(m, 2H), 3.57-3.42(m, 2H), 2.65-2.38(m, 2H), 2.30-2.12(m, 2H), 1.90-1.56(m, 3H), 0.93(d, J=6.6Hz, 3H), 0.91(d, J=6.6Hz, 3H).
실시예 24(6)
1-(티오펜-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.39(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.53(d, J=8.7Hz, 2H), 7.43-7.34(m, 2H), 7.27(dd, J=5.1, 1.2Hz, 1H), 7.18(t, J=7.2Hz, 1H), 7.09-7.00(m, 5H), 6.91(dd, J=5.1, 3.3Hz, 1H), 4.92(brs, 2H), 4.32(s, 2H), 4.11(dd, J=7.8, 4.5Hz, 1H), 3.84-3.66(m, 2H), 3.53-3.41(m, 2H), 2.68-2.46(m, 2H), 2.23-2.06(m, 2H), 1.95-1.59(m, 3H), 0.95(d, J=6.6Hz, 6H).
실시예 24(7)
1-시클로프로필메틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.40(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.53(d, J=8.7Hz, 2H), 7.43-7.35(m, 2H), 7.18(t, J=7.2Hz, 1H), 7.08-7.00(m, 4H), 4.33(s, 2H), 4.04(dd, J=7.8, 4.5Hz, 1H), 3.87-3.68(m, 2H), 3.56-3.43(m, 2H), 3.46-3.35(m, 2H), 2.56-2.35(m, 2H), 2.23-2.12(m, 2H), 1.95-1.58(m, 3H), 1.10-0.95(m, 1H), 0.95(d, J=6.6Hz, 6H), 0.56-0.45(m, 2H), 0.42-0.34(m, 2H).
실시예 24(8)
1-(2-플루오로페닐메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.43(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.48(d, J=9.0Hz, 2H), 7.42-7.34(m, 2H), 7.32-7.21(m, 1H), 7.17(t, J=7.5Hz, 1H), 7.14-7.06(m, 3H), 7.06-6.98(m, 4H), 4.80(brs, 2H), 4.30(s, 2H), 4.18(dd, J=8.1, 4.8Hz, 1H), 3.86-3.68(m, 2H), 3.50-3.35(m, 2H), 2.50-2.30(m, 1H), 2.30-2.14(m, 3H), 1.94-1.62(m, 3H), 0.97(d, J=6.3Hz, 6H).
실시예 24(9)
1-(3-메틸-2-부테닐)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.29(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.52(d, J=8.4Hz, 2H), 7.43-7.35(m, 2H), 7.18(t, J=7.5Hz, 1H), 7.09-7.00(m, 4H), 4.97(br, 1H), 4.32(s, 2H), 4.20-4.00(m, 2H), 4.02(dd, J=7.8, 4.5Hz, 1H), 3.90-3.68(m, 2H), 3.55-3.45(m, 2H), 2.52-2.32(m, 2H), 2.30-2.08(m, 2H), 1.90-1.56(m, 3H), 1.74(s, 3H), 1.69(s, 3H), 0.94(d, J=6.3Hz, 3H), 0.94(d, J=6.3Hz, 3H).
실시예 24(10)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(퀴놀린-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.25(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 9.52(d, J=1.5Hz, 1H), 9.35(d, J=1.5Hz, 1H), 8.35(d, J=8.7Hz, 1H), 8.27(d, J=8.7Hz, 1H), 8.24-8.16(m, 1H), 8.04-7.96(m, 1H), 4.76(s, 2H), 4.03(dd, J=7.5, 4.5Hz, 1H), 4.00-3.85(m, 2H), 3.68-3.55(m, 2H), 3.55-3.43(m, 2H), 2.76-2.56(m, 2H), 2.27-2.05(m, 2H), 1.82-1.10(m, 15H), 1.05-0.83(m, 2H), 0.92(t, J=7.2Hz, 3H).
실시예 24(11)
1-부틸-2,5-디옥소-3-(벤질옥시카르보닐메틸)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.74(클로로포름:메탄올=9:1);
NMR(CD3OD): δ 7.52(d, J=7.0Hz, 2H), 7.40(t, J=7.5Hz, 2H), 7.33(m, 5H), 7.18(t, J=7.5Hz, 1H), 7.05(m, 4H), 5.12(s, 2H), 4.33(s, 2H), 4.31(m, 1H), 3.88(m, 1H), 3.66(m, 1H), 3.50-3.35(m, 4H), 3.08(dd, J=17.7, 4.8Hz, 1H), 2.86(dd, J=17.7, 3.0Hz, 1H), 2.34(m, 2H), 2.25(m, 2H), 1.50(m, 2H), 1.36(m, 2H), 0.94(t, J=7.5Hz, 3H).
실시예 24(12)
1-(3-메틸-2-부테닐)-2,5-디옥소-3-시클로헥실메틸-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.63(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.04(d, J=2.1Hz, 1H), 6.96(dd, J=8.1, 2.1Hz, 1H), 6.92(d, J=8.1Hz, 1H), 4.96(m, 1H), 4.26(s, 4H), 4.22(s, 2H), 4.10-4.00(m, 3H), 3.84-3.68(m, 2H), 3.52-3.40(m, 2H), 2.43-2.08(m, 4H), 1.84-1.42(m, 13H), 1.38-1.12(m, 4H), 1.04-0.85(m, 2H).
실시예 24(13)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-((2E)-3-페닐-2-프로페닐)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.28(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.53-7.48(m, 2H), 7.30-7.40(m, 3H), 6.95(d, J=16.2Hz, 1H), 6.36(dd, J=16.2, 8.1Hz, 1H), 4.07(dd, J=7.5, 4.5Hz, 1H), 3.96(d, J=8.1Hz, 2H), 3.86-3.75(m, 2H), 3.60-3.52(m, 2H), 3.42-3.34(m, 2H), 2.42-2.18(m, 4H), 1.82-1.14(m, 15H), 0.96(t, J=7.2Hz, 3H), 0.96(m, 2H).
실시예 24(14)
(3S)-1-부틸-2,5-디옥소-3-(1,1-디메틸에틸)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.50(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.54(d, J=8.5Hz, 2H), 7.39(m, 2H), 7.18(t, J=7.5Hz, 1H), 7.08-7.02(m, 4H), 4.34(s, 2H), 3.88(m, 2H), 3.62(s, 1H), 3.46(m, 4H), 2.45(m, 2H), 2.13(m, 2H), 1.66-1.47(m, 2H), 1.36(m, 2H), 1.02(s, 9H), 0.95(t, J=7.0Hz, 3H).
실시예 24(15)
(3S)-1-부틸-2,5-디옥소-3-(1,1-디메틸에틸)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.47(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.07(m, 1H), 6.99(d, J=8.0Hz, 1H), 6.91(d, J=8.0Hz, 1H), 4.26(m, 4H), 4.24(s, 2H), 3.83(m, 2H), 3.62(s, 1H), 3.45(m, 4H), 2.42(m, 2H), 2.11(m, 2H), 1.64-1.5(m, 2H), 1.38(m, 2H), 1.01(s, 9H), 0.95(t, J=7.0Hz, 3H).
실시예 24(16)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-메틸티아졸-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.67(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.34(s, 1H), 4.73(s, 2H), 4.01(dd, J=8.0, 4.5Hz, 1H), 3.93(m, 2H), 3.65(m, 2H), 3.41(m, 2H), 2.53-2.41(m, 2H), 2.48(s, 3H), 2.23(m,2H), 1.85-1.52(m, 5H), 1.38(m, 2H), 0.96(t, J=7.0Hz, 3H), 0.94(d, J=6.5Hz, 3H), 0.93(d, J=6.5Hz, 3H).
실시예 24(17)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-메틸티아졸-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.66(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.34(s, 1H), 4.72(s, 2H), 4.04(dd, J=7.5, 4.5Hz, 1H), 3.98-3.86(m, 2H), 3.67-3.63(m, 2H), 3.44-3.38(m, 2H), 2.56-2.42(m, 2H), 2.48(s, 3H), 2.30-2.14(m, 2H), 1.84-1.18(m, 15H), 0.96(t, J=7.2Hz, 3H), 0.96(m, 2H).
실시예 24(18)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-메틸티아졸-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.63(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.63(s, 1H), 4.69(s, 2H), 4.03(dd, J=7.3, 4.5Hz, 1H), 3.96-3.82(m, 2H), 3.72-3,58(m, 2H), 3.42-3.37(m, 2H), 2.52(s, 3H), 2.56-2.36(m, 2H), 2.28-2.12(m, 2H), 1.80-1.12(m, 15H), 0.96(t, J=7.5Hz, 3H), 0.96(m, 2H).
실시예 24(19)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-메틸티아졸-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.70(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.63(s, 1H), 4.69(brs, 2H), 4.01(dd, J=7.8, 4.5Hz, 1H),3.99-3.83(m, 2H), 3.70-3.58(m, 2H), 3.44-3.34(m, 2H), 2.53(s, 3H), 2.50-2.33(m, 2H), 2.32-2.12(m, 2H), 1.88-1.46(m, 5H), 1.45-1.31(m, 2H), 1.01-0.90(m, 9H).
실시예 24(20)
(3R)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.59(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.04(d, J=2.0Hz, 1H), 6.97(dd, J=8.5, 2.0Hz, 1H), 6.93(d, J=8.5Hz, 1H), 4.26(s, 4H), 4.24(s, 2H), 4.04(dd, J=7.5, 5.0Hz, 1H), 3.76(m, 2H), 3.46(m, 4H), 2.39-2.11(m, 4H), 1.78-1.17(m, 15H), 0.95(t, J=7.0Hz, 3H), 0.95(m, 2H).
HPLC 조건
사용한 칼럼: YMC CHIRAL-CD BR, 0.46×25 cm, YMC, DB12S05-2546 WTI;
사용한 유속: 0.5 mL/분;
사용한 용매
A액: 0.1 M 인산2수소칼륨 수용액
B액: 아세토니트릴
A:B=84:16;
사용한 UV: 235 nm;
유지 시간: 18 분.
실시예 24(21)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.59(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.04(d, J=2.0Hz, 1H), 6.97(dd, J=8.5, 2.0Hz, 1H), 6.93(d, J=8.5Hz, 1H), 4.26(s, 4H), 4.24(s, 2H), 4.04(dd, J=7.5, 5.0Hz, 1H), 3.76(m, 2H), 3.46(m, 4H), 2.39-2.11(m, 4H), 1.78-1.17(m, 15H), 0.95(t, J=7.0Hz, 3H), 0.95(m, 2H).
HPLC 조건
사용한 칼럼: YMC CHIRAL-CD BR, 0.46×25 cm, YMC, DB12S05-2546 WTI;
사용한 유속: 0.5 mL/분;
사용한 용매
A액: 0.1 M 인산2수소칼륨 수용액
B액: 아세토니트릴
A:B=84:16;
사용한 UV: 235 nm;
유지 시간: 20 분.
실시예 24(22)
(3R)-1-부틸-2,5-디옥소-3-((1R)-1-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.59(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.53(d, J=8.5Hz, 2H), 7.39(m, 2H), 7.18(t, J=7.5Hz, 1H), 7.08-7.01(m, 4H), 4.33(s, 2H), 3.96(d, J=2.5Hz, 1H), 3.92(m, 1H), 3.75(m, 1H), 3.53-3.44(m, 4H), 2.49-2.32(m, 2H), 2.16(m, 2H), 2.06-1.98(m, 1H), 1.61-1.21(m, 6H), 1.00-0.89(m, 9H).
실시예 24(23)
(3S)-1-부틸-2,5-디옥소-3-((1S)-1-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.59(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.53(d, J=8.5Hz, 2H), 7.39(m, 2H), 7.18(t, J=7.5Hz, 1H), 7.08-7.01(m, 4H), 4.33(s, 2H), 3.96(d, J=2.5Hz, 1H), 3.92(m, 1H), 3.75(m, 1H), 3.53-3.44(m, 4H), 2.49-2.32(m, 2H), 2.16(m, 2H), 2.06-1.98(m, 1H), 1.61-1.21(m, 6H), 1.00-0.89(m, 9H).
실시예 24(24)
1-(2-부티닐)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.70(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.51(d, J=8.7Hz, 2H), 7.39(dd, J=8.7, 7.2Hz, 2H), 7.18(t, J=7.2Hz, 1H), 7.09-7.00(m, 4H), 4.33(brs, 2H), 4.28-4.10(m, 2H), 4.05(dd, J=7.8, 4.5Hz, 1H), 3.86-3.70(m, 2H), 3.56-3.43(m, 2H), 2.59-2.40(m, 2H), 2.34-2.15(m, 2H), 1.89-1.57(m, 6H), 0.94(d, J=6.6Hz, 3H), 0.93(d, J=6.6Hz, 3H).
실시예 24(25)
1-(2-부티닐)-2,5-디옥소-3-시클로헥실메틸-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.52(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.04(d, J=2.1Hz, 1H), 6.97(dd, J=8.4, 2.1Hz, 1H), 6.93(d, J=8.4Hz, 1H), 4.26(s, 4H), 4.23(s, 2H), 4.18(brs, 2H), 4.07(dd, J=6.9, 4.8Hz, 1H), 3.84-3.68(m, 2H), 3.55-3.42(m, 2H), 2.57-2.40(m, 2H), 2.32-2.12(m, 2H), 1.85-1.42(m, 11H), 1.38-1.13(m, 3H), 1.04-0.85(m, 2H).
실시예 24(26)
1-펜틸-2,5-디옥소-3-시클로헥실메틸-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.61(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.04(d, J=2.1Hz, 1H), 6.97(dd, J=8.4, 2.1Hz, 1H), 6.92(d, J=8.4Hz, 1H), 4.26(s, 4H), 4.22(brs, 2H), 4.03(dd, J=7.2, 4.5Hz, 1H), 3.84-3.67(m, 2H), 3.52-3.33(m, 4H), 2.43-2.07(m, 4H), 1.83-1.42(m, 9H), 1.41-1.13(m, 8H), 1.04-0.85(m, 5H).
실시예 24(27)
1-(3-메톡시페닐메틸)-2,5-디옥소-3-(벤질옥시메틸)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.45(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.60-7.43(m, 5H), 7.38-7.24(m, 5H), 7.14(t, J=8.4Hz, 1H), 6.83-6.72(m, 3H), 4.96-4.70(m, 2H), 4.60(d, J=11.4Hz, 1H), 4.50(d, J=11.4Hz, 1H), 4.29(t, J=2.4Hz, 1H), 4.24(s, 2H), 4.02(dd, J=9.6, 2.4Hz, 1H), 3.93-3.79(m, 1H), 3.72(s, 3H), 3.70(dd, J=9.6, 2.4Hz, 1H), 3.70-3.60(m, 1H), 3.55-3.44(m, 1H), 3.35-3.23(m, 1H), 2.58-2.05(m, 10H).
실시예 24(28)
(3R)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.29(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.54(d, J=8.7Hz, 2H), 7.42-7.36(m, 2H), 7.18(m, 1H), 7.05(d, J=8.7Hz, 2H), 7.05-7.02(m, 2H), 4.32(s, 2H), 4.01(dd, J=7.8, 4.8Hz, 1H), 3.85-3.72(m, 2H), 3.50-3.39(m, 4H), 2.52-2.38(m, 2H), 2.24-2.11(m, 2H), 1.84-1.20(m, 7H), 0.95(t, J=7.2Hz, 3H), 0.95(d, J=6.3Hz, 3H), 0.93(d, J=6.3Hz, 3H).
HPLC 조건
사용한 칼럼: CHIRALCEL OD-R, 0.46×25 cm, DAICEL, ODR0CE-HD028;
사용한 유속: 0.4 mL/분;
사용한 용매
A액: 0.2 M 인산2수소칼륨 수용액
B액: 아세토니트릴
A:B=64:36;
사용한 UV:235 nm;
유지 시간: 30 분.
실시예 24(29)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.29(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.54(d, J=8.7Hz, 2H), 7.42-7.36(m, 2H), 7.18(m, 1H), 7.05(d, J=8.7Hz, 2H), 7.05-7.02(m, 2H), 4.33(s, 2H), 3.98(dd, J=8.. 1, 4.5Hz, 1H), 3.86-3.72(m, 2H), 3.53-3.37(m, 4H), 2.47-2.36(m, 2H), 2.24-2.12(m, 2H ), 1.80-1.30(m, 7H), 0.95(t, J=7.2Hz, 3H), 0.95(d, J=6.3Hz, 3H), 0.93(d, J=6.3Hz, 3H).
HPLC 조건
사용한 칼럼: CHIRALCEL OD-R, 0.46×25 cm, DAICEL, ODR0CE-HD028;
사용한 유속: 0.4 mL/분;
사용한 용매
A액: 0.2 M 인산2수소칼륨 수용액
B액: 아세토니트릴
A:B=64:36;
사용한 UV: 235 nm;
유지 시간: 28 분.
실시예 24(30)
1-부틸-2,5-디옥소-3-시클로펜틸메틸-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.53(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.05(d, J=2.0Hz, 1H), 6.98(dd, J=8.5, 2.0Hz, 1H), 6.93(d, J=8.5Hz, 1H), 4.26(s, 4H), 4.23(s, 2H), 3.99(t, J=6.0Hz, 1H), 3.77(m, 2H), 3.46(m, 2H), 3.37(m, 2H), 2.36(m, 2H), 2.15(m, 2H), 1.96(m, 1H), 1.81(m, 4H), 1.59(m, 6H), 1.36(m, 2H), 1.15(m, 2H), 0.95(t, J=7.0Hz, 3H).
실시예 24(31)
1-프로필-2,5-디옥소-3-(시클로헥실메틸옥시메틸)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.63(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.59-7.46(m, 5H), 4.33(s, 2H), 4.08(m, 1H), 4.00(m, 1H), 3.83(m, 1H), 3.77(m, 1H), 3.59(m, 2H), 3.52(m, 1H), 3.25(d, J=6.5Hz, 2H), 2.53(m, 2H), 2.42(m, 1H), 2.40(s, 3H), 2.39(s, 3H), 2.21(m, 2H), 1.69(m, 6H), 1.52(m, 2H), 1.21(m, 4H), 0.95(t, J=7.0Hz, 3H), 0.88(m, 2H).
실시예 24(32)
(3S)-1-부틸-2,5-디옥소-3-(1-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.47(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.06-6.90(m, 3H), 4.26(s, 4H), 4.23(s, 2H), 3.95(d,J=3.3Hz, 1H), 3.87(m, 1H), 3.70(m, 1H), 3.58-3.42(m, 4H), 2.56-2.30(m, 2H), 2.20-1.98(m, 2H), 1.54-1.00(m, 7H), 0.99(d, J=7.2Hz, 3H), 0.95(t, J=7.5Hz, 3H), 0.91(t, J=7.5Hz, 3H).
실시예 24(33)
(3R)-1-부틸-2,5-디옥소-3-(1-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.47(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.06-6.91(m, 3H), 4.26(s, 4H), 4.23(s, 2H), 3.95(d, J=3.3Hz, 1H), 3.87(m, 1H), 3.70(m, 1H), 3.56-3.40(m, 4H), 2.50-2.32(m, 2H), 2.18-1.96(m, 2H), 1.62-1.17(m, 7H), 0.99(d, J=7.2Hz, 3H), 0.95(t, J=7.2Hz, 3H), 0.91(t, J=7.5Hz, 3H).
실시예 24(34)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐메틸티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.56(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.32-7.21(m, 5H), 7.17(d, J=3.6Hz, 1H), 6.89(d, J=3.6Hz, 1H), 4.51(s, 2H), 4.17(s, 2H), 4.00(dd, J=7.8Hz, 4.5Hz, 1H), 3.84-3.72(m, 2H), 3.56-3.44(m, 2H), 3.38-3.32(m, 2H), 2.42-2.14(m, 4H), 1.84-1.30(m, 7H), 0.95(t, J=6.9Hz, 3H), 0.94(d, J=6.3Hz, 3H), 0.92(d, J=6.3Hz, 3H).
실시예 24(35)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-페닐메틸티오펜-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.59(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.32-7.21(m, 5H), 7.18(d, J=3.6Hz, 1H), 6.89(d, J=3.6Hz,1H), 4.51(s, 2H), 4.17(s, 2H), 4.03(dd, J=7.8, 4.8Hz, 1H), 3.84-3.72(m, 2H), 3.58-3.44(m, 2H), 3.40-3.36(m, 2H), 2.44-2.08(m, 4H), 1.81-1.07(m, 15H), 0.95(t, J=7.2Hz, 3H), 0.95(m, 2H).
실시예 24(36)
(3R)-1-부틸-2,5-디옥소-3-(2,2-디메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.41(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.05(s, 1H), 6.98(d, J=8.4Hz, 1H), 6.92(d, J=8.4Hz, 1H), 4.26(s, 4H), 4.23(s, 2H), 4.00(dd, J=7.0, 3.0Hz, 1H), 3.83-3.64(m, 2H), 3.50(m, 2H ), 3.38(m, 2H), 2.35(m, 2H), 2.25(m, 2H), 1.99(m, 1H), 1.55(m, 1H), 1.50(m, 2H), 1.35(m, 2H), 0.99(s, 9H), 0.95(t, J=7.0Hz, 3H).
실시예 24(37)
(3S)-1-부틸-2,5-디옥소-3-(2,2-디메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.41(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.05(s, 1H), 6.98(d, J=8.4Hz, 1H), 6.92(d, J=8.4Hz, 1H), 4.26(s, 4H), 4.23(s, 2H), 4.00(dd, J=7.0, 3.0Hz, 1H), 3.83-3.63(m, 2H), 3.50(m, 2H ), 3.38(m, 2H), 2.35(m, 2H), 2.25(m, 2H), 1.99(dd, J=14.0, 3.0Hz, 1H), 1.55(dd, J=14.0, 7.0Hz, 1H), 1.50(m, 2H), 1.35(m, 2H), 0.99(s, 9H), 0.95(t, J=7.0Hz, 3H).
실시예 24(38)
(3R)-1-(2-부티닐)-2,5-디옥소-3-(2,2-디메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.60(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.51(d, J=8.7Hz, 2H), 7.39(dd, J=8.7, 7.5Hz, 2H), 7.18(t, J=7.5Hz, 1H), 7.10-7.00(m, 4H), 4.33(brs, 2H), 4.33-4.09(m, 2H), 4.03(dd, J=6.9, 3.3Hz, 1H), 3.85-3.68(m, 2H), 3.58-3.43(m, 2H), 2.59-2.41(m, 2H), 2.40-2.20(m, 2H), 2.03(dd, J=14.4, 3.3Hz, 1H), 1.75(brs, 3H), 1.56(dd, J=14.4, 6.9Hz, 1H), 0.99(s, 9H).
실시예 24(39)
(3S)-1-(2-부티닐)-2,5-디옥소-3-(2,2-디메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.60(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.51(d, J=8.7Hz, 2H), 7.39(dd, J=8.7, 7.5Hz, 2H), 7.18(t, J=7.5Hz, 1H), 7.10-7.00(m, 4H), 4.33(brs, 2H), 4.33-4.09(m, 2H), 4.03(dd, J=6.9, 3.3Hz, 1H), 3.85-3.68(m, 2H), 3.58-3.43(m, 2H), 2.59-2.41(m, 2H), 2.40-2.20(m, 2H), 2.03(dd, J=14.4, 3.3Hz, 1H), 1.75(brs, 3H), 1.56(dd, J=14.4, 6.9Hz, 1H), 0.99(s, 9H).
실시예 24(40)
1-부틸-2,5-디옥소-3-시클로헵틸메틸-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.70(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.04(d, J=2.1Hz, 1H), 6.97(dd, J=8.4, 2.1Hz, 1H), 6.93(d, J=8.4Hz, 1H), 4.26(s, 4H), 4.24(s, 2H), 3.99(dd, J=8.1, 4.2Hz, 1H), 3.84-3.70(m, 2H), 3.45(m, 2H), 3.36(m, 2H), 2.37-2.11(m, 4H), 1.80-1.49(m, 15H), 1.36(m, 2H), 1.22(m, 2H), 0.95(t, J=7.5Hz, 3H).
실시예 24(41)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2,4,6-트리메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.55(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 6.31(s, 2H), 4.26(s, 2H), 4.03(dd, J=7.8, 4.5Hz, 1H), 3.89(s, 6H), 3.84(s, 3H), 3.84-3.73(m, 2H), 3.54-3.33(m, 4H), 2.44-2.25(m, 2H), 2.24-2.03(m, 2H), 1.84-1.12(m, 15H), 1.06-0.85(m, 5H).
실시예 24(42)
1-부틸-2,5-디옥소-3-(3-시클로헥실프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.71(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.05-6.91(m, 3H), 4.26(s, 4H), 4.22(s, 2H), 4.04(t, J=5.4Hz, 1H), 3.84(m, 1H), 3.67(m, 1H), 3.54-3.40(m, 3H), 3.35(m, 1H), 2.44-2.08(m, 4H), 1.90-1.16(m, 19H), 0.95(t, J=7.5Hz, 3H), 0.95(m, 2H).
실시예 24(43)
1-부틸-2,5-디옥소-3-(3-시클로헥실프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.76(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.53-7.49(m, 2H), 7.42-7.36(m, 2H), 7.18(m, 1H), 7.10-7.02(m, 4H), 4.32(s, 2H), 4.04(t, J=4.8Hz, 1H), 3.87(m, 1H), 3.71(m, 1H), 3.56-3.40(m, 3H), 3.35(m, 1H), 2.48-2.12(m, 4H), 1.86-1.10(m, 19H), 0.95(t, J=7.5Hz, 3H), 0.95(m, 2H).
실시예 24(44)
1-부틸-2,5-디옥소-3-(3-시클로헥실프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.64(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.59-7.45(m, 5H), 4.31(s, 2H), 4.06(t, J=5.0Hz, 1H), 3.92(m, 1H), 3.77(m, 1H), 3.63-3.37(m, 4H), 2.44(m, 2H), 2.39(s, 3H), 2.38(s, 3H), 2.21(m, 2H), 1.85-1.6 8(m, 7H), 1.54(m, 2H), 1.39(m, 4H), 1.23(m, 6H), 0.96(t, J=7.5Hz, 3H), 0.89(m, 2H).
실시예 24(45)
1-부틸-2,5-디옥소-3-(2-히드록시-2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.52(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.50(d, J=8.7Hz, 2H), 7.39(dd, J=8.7, 7.5Hz, 2H), 7.18(t, J=7.5Hz, 1H), 7.09-7.00(m, 4H), 4.32(brs, 2H), 4.29(dd, J=9.9, 3.0Hz, 1H), 4.04-3.88(m, 2H), 3.59-3.40(m, 4H), 2.46-2.21(m, 4H), 2.18(dd, J=14.4, 3.0Hz, 1H), 1.75(dd, J=14.4, 9.9Hz, 1H), 1.61-1.43(m, 2H), 1.42-1.29(m, 2H), 1.28(s, 6H), 0.95(t, J=7.5Hz, 3H).
실시예 24(46)
1-(2-부티닐)-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.41(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.61-7.45(m, 5H), 4.32(s, 2H), 4.31-4.18(m, 2H), 4.06(dd, J=7.8, 4.5Hz, 1H), 3.93-3.77(m, 2H), 3.68-3.57(m, 2H), 2.72-2.57(m, 2H), 2.40(s, 3H), 2.38(s, 3H), 2.36-2.16(m, 2H), 1.92-1.59(m, 6H), 0.95(d, J=6.6Hz, 3H), 0.94(d, J=6.6Hz, 3H).
실시예 24(47)
1-(2-부티닐)-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.37(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.60-7.43(m, 5H), 4.32(s, 2H), 4.23(d, J=2.1Hz, 2H),4.09(dd, J=7.2, 4.8Hz, 1H), 3.92-3.78(m, 2H), 3.68-3.56(m, 2H), 2.66-2.51(m, 2H), 2.38(s, 3H), 2.36(s, 3H), 2.36-2.16(m, 2H), 1.83-1.60(m, 10H), 1.59-1.43(m, 1H), 1.38-1.12(m, 3H), 1.06-0.87(m, 2H).
실시예 24(48)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.35(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.63-7.48(m, 5H), 4.33(s, 2H), 4.05(dd, J=7.8, 4.5Hz, 1H), 3.95-3.74(m, 2H), 3.67-3.56(m, 2H), 3.48(m, 2H), 2.72-2.58(m, 2H), 2.45(s, 3H), 2.41(s, 3H), 2.30-2.07(m, 2H), 1.84-1.10(m, 15H), 1.02-0.92(m, 2H), 0.96(t, J=7.2Hz, 3H).
실시예 24(49)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐옥시피리딘-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.23(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.19(m, 1H), 8.07(m, 1H), 7.47-7.42(m, 2H), 7.29-7.19(m, 4H), 4.55(s, 2H), 4.03(dd, J=7.8, 4.5Hz, 1H), 3.94(m, 2H), 3.64(m, 2H), 3.38(m, 2H), 2.54-2.16(m, 4H), 1.90-1.28(m, 7H), 0.96(t, J=6.9Hz, 3H), 0.96(d, J=6.3Hz, 3H), 0.94(d, J=6.3Hz, 3H).
실시예 24(50)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-페닐옥시피리딘-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.62(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.19(m, 1H), 8.09(m, 1H), 7.47-7.42(m, 2H), 7.29-7.19(m,4H), 4.55(s, 2H), 4.05(dd, J=7.8, 4.8Hz, 1H), 3.96(m, 2H), 3.64(m, 2H), 3.42(m, 2H), 2.48(m, 2H), 2.36-2.16(m, 2H), 1.82-1.14(m, 15H), 0.96(t, J=7.5Hz, 3H), 0.95-0.84(m, 2H).
실시예 24(51)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-메틸벤조모르폴린-7-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.69(클로로포름:메탄올=10:1);
NMR(CDCl3):δ 6.93(d, J=8.7Hz, 1H), 6.86(s, 1H), 6.75(d, J=8.7Hz, 1H), 4.28-4.25(m, 2H), 4.17(s, 2H), 4.03(dd, J=7.5, 4.5Hz, 1H), 3.80-3.65(m, 2H), 3.50-3.40(m, 2H), 3.40-3.30(m, 2H), 2.91(s, 3H), 2.38-2.06(m, 4H), 1.78-1.63(m, 8H), 1.63-1.42(m, 3H), 1.40-1.18(m, 6H), 1.05-0.90(m, 2H), 0.95(t, J=7.2Hz, 3H).
실시예 24(52)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-메틸벤조모르폴린-7-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.56(클로로포름:메탄올=10:1);
NMR(CDCl3):δ 7.00(d, J=7.2Hz, 1H), 6.94(s, 1H), 6.85(d, J=7.2Hz, 1H), 4.31-4.29(m, 2H), 4.19(s, 2H), 4.00(dd, J=7.8, 4.5Hz, 1H), 3.79-3.66(m, 2H), 3.47-3.34(m, 6H), 2.97(s, 3H), 2.45-2.34(m, 2H), 2.22-2.10(m, 2H), 1.84-1.75(m, 1H), 1.71-1.46(m, 4H), 1.42-1.32(m, 2H), 0.97-0.92(m, 9H).
실시예 24(53)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(N-메틸-N-페닐아미노)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.40(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.40-7.28(m, 4H), 7.19-7.10(m, 3H), 6.94-6.86(m, 2H),4.23(s, 2H), 4.00(dd, J=7.8, 4.5Hz, 1H), 3.86-3.63(m, 2H), 3.55-3.30(m, 4H), 3.31(s, 3H), 2.46-2.27(m, 2H), 2.26-2.06(m, 2H), 1.90-1.42(m, 5H), 1.44-1.26(m, 2H), 0.98-0.91(m, 9H).
실시예 24(54)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(N-메틸-N-페닐아미노)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.52(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.40-7.28(m, 4H), 7.20-7.12(m, 3H), 6.93-6.86(m, 2H), 4.24(s, 2H), 4.03(dd, J=7.5, 4.8Hz, 1H), 3.85-3.66(m, 2H), 3.55-3.40(m, 2H), 3.40-3.30(m, 2H), 3.32(s, 3H), 2.44-2.07(m, 4H), 1.84-1.40(m, 10H), 1.40-1.10(m, 5H), 1.06-0.85(m, 2H), 0.95(t, J=7.5Hz, 3H).
실시예 24(55)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-(3,5-디메틸피라졸-1-일)-5-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.58(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.53(d, J=3.0Hz, 1H), 7.44(d, J=8.7Hz, 1H), 7.22(dd, J=8.7, 3.0Hz, 1H), 6.29(s, 1H), 4.09(s, 2H), 4.02(dd, J=7.5, 4.5Hz, 1H), 3.94(s, 3H), 3.74(m, 2H), 3.42(m, 4H), 2.44(m, 2H), 2.37(s, 3H), 2.22(s, 3H), 2.22(m, 2H), 1.86-1.30(m, 7H), 0.96(t, J=7.8Hz, 3H), 0.95(d, J=6.3Hz, 3H), 0.94(d, J=6.3Hz, 3H).
실시예 24(56)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-(3,5-디메틸피라졸-1-일)-5-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.61(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.43(d, J=8.7Hz, 1H), 7.40(d, J=2.7Hz, 1H), 7.22(dd, J=8.7, 2.7Hz, 1H), 6.22(s, 1H), 4.09(s, 2H), 4.06(dd, J=7.5, 4.2Hz, 1H), 3.93(s, 3H), 3.80(m, 2H), 3.42(m, 4H), 2.38(m, 2H ), 2.34(s, 3H), 2.22(s, 3H), 2.20(m, 2H), 1.80-1.16(m, 15H), 0.96(t, J=7.2Hz, 3H), 0.96(m, 2H).
실시예 24(57)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디에틸-1-(4-클로로페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.47(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.53(d, J=9.0Hz, 2H), 7.49(d, J=9.0Hz, 2H), 4.31(s, 2H), 4.02(dd, J=7.8, 4.5Hz, 1H), 3.94-3.73(m, 2H), 3.65-3.54(m, 2H), 3.49-3.38(m, 2H), 2.88(q, J=7.5Hz, 2H), 2.77(q, J=7.5Hz, 2H), 2.58-2.38(m, 2H), 2.30-2.12(m, 2H), 1.90-1.56(m, 5H), 1.55-1.30(m, 2H), 1.31(t, J=7.5Hz, 3H), 0.99-0.94(m, 12H).
실시예 24(58)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디에틸-1-(4-클로로페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.51(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.58(d, J=9.0Hz, 2H), 7.48(d, J=9.0Hz, 2H), 4.31(s, 2H), 4.05(dd, J=7.5, 4.5Hz, 1H), 3.94-3.73(m, 2H), 3.65-3.54(m, 2H), 3.50-3.38(m, 2H), 2.88(q, J=7.5Hz, 2H), 2.77(q, J=7.5Hz, 2H), 2.60-2.40(m, 2H), 2.28-2.09(m, 2H), 1.85-1.10(m, 15H), 1.31(t, J=7.5Hz, 3H), 1.04-0.85(m, 2H), 0.96(t, J=7.5Hz, 3H), 0.94(t, J=7.5Hz, 3H).
실시예 24(59)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐옥시피리딘-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.65(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.32(s, 1H), 8.06(m, 1H), 7.44(t, J=7.5Hz, 2H), 7.26(t, J=7.5Hz, 1H), 7.14(d, J=7.5Hz, 2H), 7.06(d, J=8.7Hz, 1H), 4.39(s, 2H), 4.01(dd, J=7.5, 4.5Hz, 1H), 3.90-3.70(m, 2H), 3.53-3.41(m, 4H), 2.45(m, 2H), 2.25-2.12(m, 2H), 1.78(m, 1H), 1.72-1.50(m, 4H), 1.36(m, 2H), 0.97-0.93(m, 9H).
실시예 24(60)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(6-페닐옥시피리딘-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.67(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.31(s, 1H), 8.07(d, J=8.3Hz, 1H), 7.44(t, J=7.5Hz, 2H), 7.26(t, J=7.5Hz, 1H), 7.14(d, J=7.5Hz, 2H), 7.06(d, J=8.3Hz, 1H), 4.39(s, 2H), 4.04(dd, J=7.8, 4.6Hz, 1H), 3.90-3.76(m, 2H), 3.52-3.38(m, 4H), 2.58-2.36(m, 2H), 2.25-2.11(m, 2H), 1.80-1.42(m, 10H), 1.42-1.17(m, 5H), 1.05-0.85(m, 2H), 0.95(t, J=7.2Hz, 3H).
실시예 24(61)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(1,3-벤조디옥솔란-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.38(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.05-7.00(m, 2H), 6.92(m, 1H), 6.03(s, 2H), 4.26(s, 2H), 4.02(dd, J=7.5, 4.5Hz, 1H), 3.84-3.68(m, 2H), 3.52-3.36(m, 4H), 2.42-2.10(m, 4H), 1.88-1.32(m, 7H), 0.96(t, J=6.9Hz, 3H), 0.95(d, J=6.3Hz, 3H), 0.94(d, J=6.3Hz, 3H).
실시예 24(62)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(1,3-벤조디옥솔란-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.42(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.06-7.01(m, 2H), 6.92(m, 1H), 6.03(s, 2H), 4.27(s, 2H), 4.04(dd, J=7.5, 4.5Hz, 1H), 3.82-3.70(m, 2H), 3.56-3.36(m, 4H), 2.48-2.10(m, 4H), 1.82-1.16(m, 15H), 0.96(t, J=7 . 5Hz, 3H), 0.96(m, 2H).
실시예 24(63)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-히드록시-4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.88(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.26(d, J=8.5Hz, 1H), 6.51(dd, J=8.5, 2.5Hz, 1H), 6.48(d, J=2.5Hz, 1H), 4.26(s, 2H), 4.03(m, 1H), 3.77(m, 5H), 3.47(m, 2H), 3.37(m, 2H), 2.34(m, 2H), 2.15(m, 2H), 1.69(m, 6H), 1.52(m, 4H), 1.31(m, 5H), 0.95(m, 5H).
실시예 24(64)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-메틸티오페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.83(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.44(d, J=8.7Hz, 2H), 7.36(d, J=8.7Hz, 2H), 4.32(s, 2H), 4.03(dd, J=7.5, 4.5Hz, 1H), 3.80(m, 2H), 3.49(m, 2H), 3.34(m, 2H), 2.50(s, 3H), 2.36-2.11(m, 4H), 1.69(m, 10H), 1.39-1.23(m, 5H), 0.95(m, 5H).
실시예 24(65)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(N,N-디페닐아미노)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.48(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.40-7.25(m, 6H), 7.13-7.01(m, 8H), 4.27(s, 2H),4.01(dd, J=7.8, 4.5Hz, 1H), 3.87-3.68(m, 2H), 3.56-3.44(m, 2H), 3.44-3.32(m, 2H), 2.48-2.32(m, 2H), 2.29-2.10(m, 2H), 1.90-1.44(m, 5H), 1.44-1.30(m, 2H), 0.96(t, J=6.9Hz, 3H), 0.94(d, J=6.3Hz, 3H), 0.94(d, J=6.3Hz, 3H).
실시예 24(66)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(N,N-디페닐아미노)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.53(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.41-7.26(m, 6H), 7.14-7.00(m, 8H), 4.27(s, 2H), 4.04(dd, J=7.5, 4.5Hz, 1H), 3.88-3.68(m, 2H), 3.57-3.45(m, 2H), 3.44-3.36(m, 2H), 2.48-2.32(m, 2H), 2.28-2.07(m, 2H), 1.84-1.44(m, 10H), 1.44-1.14(m, 5H), 1.00-0.90(m, 2H), 0.96(t, J=6.9Hz, 3H).
실시예 24(67)
(3S)-1-(2-부티닐)-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.32(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.59-7.46(m, 5H), 4.32(s, 2H), 4.24(s, 2H), 4.09(dd, J=7.5, 4.5Hz, 1H), 3.86(m, 2H), 3.65(m, 2H), 2.60(m, 2H), 2.39(s, 3H), 2.38(s, 3H), 2.26(m, 2H), 1.88-1.66(m, 10H), 1.53(m, 1H), 1.25(m, 3H), 0.96(m, 2H).
실시예 24(68)
(3S)-1-(2-부티닐)-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.43(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.60-7.46(m, 5H), 4.32(s, 2H), 4.26(m, 2H), 4.06(dd,J=7.5, 4.5Hz, 1H), 3.85(m, 2H), 3.62(m, 2H), 2.60(m, 2H), 2.39(s, 3H), 2.38(s, 3H), 2.27(m, 2H), 1.89-1.61(m, 6H), 0.95(d, J=6.5Hz, 3H), 0.94(d, J=6.5Hz, 3H).
실시예 24(69)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.57(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.59-7.45(m, 5H), 4.32(s, 2H), 4.06(dd, J=7.8, 4.5Hz, 1H), 3.85(m, 2H), 3.60(m, 2H), 3.43(m, 2H), 2.53-2.44(m, 2H), 2.45(s, 3H), 2.41(s, 3H), 2.32-2.16(m, 2H), 1.80-1.17(m, 15H), 1.02-0.93(m, 2H), 0.96(d, J=7.0Hz, 3H).
실시예 24(70)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-메틸페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.46(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.36(d, J=8.4Hz, 2H), 7.31(d, J=8.4Hz, 2H), 4.30(s, 2H), 4.02(dd, J=7.8, 4.8Hz, 1H), 3.84(m, 2H), 3.60(m, 2H), 3.38(m, 2H), 2.42(s, 3H), 2.37(s, 3H), 2.35(s, 3H), 2.52-2.18(m, 4H), 1.90-1.32(m, 7H), 0.96(t, J=7.8Hz, 3H), 0.95(d, J=6.3Hz, 3H), 0.94(d, J=6.3Hz, 3H).
실시예 24(71)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-메틸페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.51(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.38(d, J=8.4Hz, 2H), 7.33(d, J=8.4Hz, 2H), 4.31(s, 2H),4.06(dd, J=7.5, 4.5Hz, 1H), 3.82(m, 2H), 3.60(m, 2H), 3.42(m, 2H), 2.43(s, 3H), 2.38(s, 3H), 2.36(s, 3H), 2.56-2.14(m, 3H), 1.84-1.16(m, 15H), 0.97(t, J=7.2Hz, 3H), 0.97(m, 2H).
실시예 24(72)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-클로로페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.30(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.57(d, J=9.0Hz, 2H), 7.49(d, J=9.0Hz, 2H), 4.31(s, 2H), 4.02(dd, J=7.8, 4.5Hz, 1H), 3.91-3.80(m, 2H), 3.60(m, 2H), 3.46(m, 2H), 2.52(m, 2H), 2.40(s, 3H), 2.39(s, 3H), 2.27-2.15(m, 2H), 1.86-1.81(m, 1H), 1.76-1.51(m, 4H), 1.44-1.32(m, 2H), 0.96(t, J=7.0Hz, 3H), 0.95(d, J=6.0Hz, 3H), 0.94(d, J=6.0Hz, 3H).
실시예 24(73)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-클로로페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.27(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.57(d, J=8.5Hz, 2H), 7.48(d, J=8.5Hz, 2H), 4.31(s, 2H), 4.04(dd, J=7.8, 4.5Hz, 1H), 3.91-3.77(m, 2H), 3.60(m, 2H), 3.45(m, 2H), 2.50(m, 2H), 2.39(s, 6H), 2.27-2.14(m, 2H), 1.80-1.51(m, 9H), 1.44-1.17(m, 6H), 1.03-0.89(m, 5H).
실시예 24(74)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-트리플루오로메틸페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.23(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.87(d, J=8.7Hz, 2H), 7.72(d, J=8.7Hz, 2H), 4.32(s, 2H),4.02(dd, J=7.8, 4.5Hz, 1H), 3.93-3.78(m, 2H), 3.60(m, 2H), 3.43(m, 2H), 2.50(m, 2H), 2.45(s, 3H), 2.40(s, 3H), 2.29-2.16(m, 2H), 1.86-1.77(m, 1H), 1.74-1.54(m, 4H), 1.44-1.34(m, 2H), 0.96(t, J=7.0Hz, 3H), 0.95(d, J=6.0Hz, 3H), 0.94(d, J=6.0Hz, 3H).
실시예 24(75)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-트리플루오로메틸페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.37(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.87(d, J=8.4Hz, 2H), 7.72(d, J=8.4Hz, 2H), 4.32(s, 2H), 4.05(dd, J=7.8, 4.5Hz, 1H), 3.92-3.78(m, 2H), 3.60(m, 2H), 3.45(m, 2H), 2.50(m, 2H), 2.45(s, 3H), 2.40(s, 3H), 2.28-2.15(m, 2H), 1.80-1.51(m, 9H), 1.44-1.21(m, 6H), 1.03-0.93(m, 5H).
실시예 24(76)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디에틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.70(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.61-7.53(m, 3H), 7.53-7.46(m, 2H), 4.32(s, 2H), 4.03(dd, J=7.5, 4.5Hz, 1H), 3.95-3.79(m, 2H), 3.65-3.58(m, 2H), 3.50-3.38(m, 2H), 2.85-2.75(m, 4H), 2.47(br, 2H), 2.28-2.16(m, 2H), 1. 83-1.46(m, 3H), 1.41-1.29(m, 4H), 0.98-0.91(m, 15H).
실시예 24(77)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디에틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.67(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.61-7.53(m, 3H), 7.53-7.46(m, 2H), 4.32(s, 2H),4.05(dd, J=7.5, 4.5Hz, 1H), 3.95-3.79(m, 2H), 3.70-3.55(m, 2H), 3.47-3.31(m, 2H), 2.91-2.75(m, 4H), 2.60-2.45(m, 2H), 2.30-2.14(m, 2H), 1.80-1.43(m, 9H), 1.43-1.15(m, 8H), 0.98-0.91(m, 9H).
실시예 24(78)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-페닐티아졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.62(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.03-8.00(m, 2H), 7.87(s, 1H), 7.52-7.49(m, 3H), 4.54(s, 2H), 4.04(dd, J=7.6, 4.8Hz, 1H), 4.04-3.87(m, 2H), 3.70-3.58(m, 2H), 3.51-3.39(m, 2H), 2.58-2.38(m, 2H), 2.26-2.13(m, 2H), 1.7 8-1.43(m, 9H), 1.40-1.15(m, 6H), 1.10-0.90(m, 5H).
실시예 24(79)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐티아졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.38(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.02-8.01(m, 2H), 7.85(s, 1H), 7.51-7.50(m, 3H), 4.55(s, 2H), 4.03-3.86(m, 3H), 3.68-3.59(m, 2H), 3.45-3.36(m, 2H), 2.50-2.34(m, 2H), 2.29-2.16(m, 2H), 1.88-1.45(m, 5H), 1.36(q, J=7.2Hz, 2H), 0.97-0.93(m, 9H).
실시예 24(80)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-(1,4-벤조디옥산-2-일)티아졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.36(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.88(s, 1H), 7.00(m, 1H), 6.94-6.87(m, 3H), 5.66(dd, J=6.0, 2.7Hz, 1H), 4.62(dd, J=11.7, 2.7Hz, 1H), 4.51(s, 2H), 4.42(dd, J=11.7,6.0Hz, 1H), 4.02(dd, J=7.5, 4.5Hz, 1H), 3.88(m, 2H), 3.58(m, 2H), 3.40(m, 2H), 2.48-2.16(m, 4H), 1.90-1.28(m, 7H), 0.97(t, J=7.5Hz, 3H), 0.95(d, J=6.3Hz, 3H), 0.94(d, J=6.3Hz, 3H).
실시예 24(81)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-트리플루오로메틸-2-(모르폴린-1-일)티아졸-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.78(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 4.63(s, 2H), 4.03(dd, J=7.8, 4,8Hz, 1H), 3.86-3.78(m, 6H), 3.58(m, 6H), 3.40(m, 2H), 2.44(m, 2H), 2.22(m, 2H), 1.88-1.32(m, 8H), 0.97(t, J=7.2Hz, 3H), 0.95(d, J=6.6Hz, 3H), 0.94(d, J=6.6Hz, 3H).
실시예 24(82)
1-부틸-2,5-디옥소-3-(테트라히드로피란-4-일메틸)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.31(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.60-7.46(m, 5H), 4.33(s, 2H), 4.09(dd, J=7.5, 4.5Hz, 1H), 3.98-3.78(m, 4H), 3.68-3.56(m, 2H), 3.50-3.36(m, 4H), 2.58-2.16(m, 4H), 2.40(s, 3H), 2.39(s, 3H), 1.84-1.20(m, 11H), 0.97(t, J=7.2Hz, 3H).
실시예 24(83)
1-부틸-2,5-디옥소-3-(테트라히드로피란-4-일메틸)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.34(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.06-6.92(m, 3H), 4.27(s, 4H), 4,24(s, 2H), 4.07(dd,J=7.5, 4.5Hz, 1H), 3.96-3.86(m, 2H), 3.84-3.68(m, 2H), 3.52-3.36(m, 6H), 2.44-2.10(m, 4H), 1.82-1.22(m, 11H), 0.96(t, J=7.2Hz, 3H).
실시예 24(84)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-카르복시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.58(클로로포름:메탄올:초산=20:2:1);
NMR(CD3OD): δ 8.14(d, J=8.4Hz, 2H), 7.68(d, J=8.4Hz, 2H), 4.45(s, 2H), 4.04(dd, J=7.5, 4.5Hz, 1H), 3.94-3.76(m, 2H), 3.56-3.43(m, 2H), 3.43-3.34(m, 2H), 2.50-2.31(m, 2H), 2.28-2.08(m, 2H), 1.84-1.12(m, 15H), 1.06-0.90(m, 2H), 0.95(t, J=7.2Hz, 3H).
실시예 24(85)
1-부틸-2,5-디옥소-3-(2-시클로헥실에틸)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.47(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.56-7.45(m, 5H), 4.32(s, 2H), 4.02(t, J=4.8Hz, 1H), 3.98-3.85(m, 1H), 3.85-3.70(m, 1H), 3.65-3.56(m, 2H), 3.56-3.42(m, 1H), 3.42-3.30(m, 1H), 2.55-2.37(m, 2H), 2.38(s, 3H), 2.37(s, 3H), 2.30-2.13(m, 2H), 1.92-1.78(m, 2H), 1.78-1.60(m, 5H), 1.60-1.48(m, 2H), 1.48-1.32(m, 2H), 1.32-1.08(m, 6H), 0.96(t, J=7.2Hz, 3H), 0.96-0.85(m, 2H).
실시예 24(86)
1-부틸-2,5-디옥소-3-(2-시클로헥실에틸)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.50(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.05(d, J=2.1Hz, 1H), 6.98(dd, J=8.1, 2.1Hz, 1H), 6.92(d, J=8.1Hz, 1H), 4.26(s, 4H), 4.23(s, 2H), 4.03(t, J=4.8Hz, 1H), 3.90-3.79(m, 1H), 3.76-3.62(m, 1H), 3.50-3.38(m, 3H), 3 . 38-3.30(m, 1H), 2.43-2.06(m, 4H), 1.92-1.78(m, 2H), 1.78-1.60(m, 5H), 1.60-1.45(m, 2H), 1.42-1.30(m, 2H), 1.30-1.08(m, 6H), 0.95(t, J=7.2Hz, 3H), 0.97-0.88(m, 2H).
실시예 24(87)
(3R)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.43(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.61-7.48(m, 5H), 4.33(s, 2H), 4.06(dd, J=7.5, 4.5Hz, 1H), 3.95-3.78(m, 2H), 3.68-3.58(m, 2H), 3.50-3.40(m, 2H), 2.62-2.45(m, 2H), 2.42(s, 3H), 2.40(s, 3H), 2.30-2.12(m, 2H), 1.82-1.12(m, 15H), 0.97(t, J=7 . 2Hz, 3H), 0.97(m, 2H).
실시예 24(88)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-메틸-2-페닐티아졸-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.75(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.98-7.95(m, 2H), 7.55-7.50(m, 3H), 4.69(s, 2H), 4.01(dd, J=7.5, 4.5Hz, 1H), 3.98-3.78(m, 2H), 3.65-3.56(m, 2H), 3.50-3.40(m, 2H), 2.58(s, 3H), 2.60-2.48(m, 2H), 2.27-2.14(m, 2H), 1.88-1.48(m, 5H), 1.48-1.30(m, 2H), 0.97-0.93(m, 9H).
실시예 24(89)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-(티오펜-1-일)티아졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.60(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.81(s, 1H), 7.67(d, J=3.9Hz, 1H), 7.60(d, J=5.4Hz, 1H),7.14(dd, J=5.4, 3.9Hz, 1H), 4.49(s, 2H), 4.00(dd, J=7.8, 4.5Hz, 1H), 3.98-3.82(m, 2H), 3.62-3.55(m, 2H), 3.42(t, J=7 . 5Hz, 2H), 2.58-2.40(m, 2H), 2.28-2.10(m, 2H), 1.86-1.42(m, 5H), 1.46-1.30(m, 2H), 0.97-0.93(m, 9H).
실시예 24(90)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-(피리딘-4-일)티아졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.51(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.98(d, J=6.9Hz, 2H), 8.71(d, J=6.9Hz, 2H), 8.37(s, 1H), 4.66(s, 2H), 4.01(dd, J=7.8, 4.8Hz, 1H), 4.00-3.87(m, 2H), 3.70-3.59(m, 2H), 3.50(t, J=7.8Hz, 2H), 2.72-2.58(m, 2H), 2.25-2.08(m, 2H), 1.88-1.46(m, 5H), 1.46-1.35(m, 2H), 0.97-0.92(m, 9H).
실시예 24(91)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,4-디메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.28(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.23(s, 1H), 7.09(d, J=8.4Hz, 1H), 7.03(d, J=8.4Hz, 1H), 4.29(s, 2H), 4.04(dd, J=7.5, 4.8Hz, 1H), 3.90(s, 3H), 3.86(s, 3H), 3.88-3.64(m, 2H), 3.56-3.38(m, 4H), 2.58-2.37(m, 2H), 2.24-2.08(m, 2H), 1.82-1.10(m, 15H), 0.96(t, J=7.2Hz, 3H), 0.96(m, 2H).
실시예 24(92)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.31(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 6.74(d, J=1.8Hz, 2H), 6.60(t, J=1.8Hz, 1H), 4.28(s, 2H), 4.04(dd, J=7.8, 4.8Hz, 1H), 3.86-3.70(m, 2H), 3.83(s, 6H), 3.58-3.36(m, 4H), 2.52-2.36(m, 2H), 2.24-2.08(m, 2H), 1.82-1.10(m, 15H), 0.96(t, J=7.2Hz, 3H), 0.96(m, 2H).
실시예 24(93)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(피리딘-2-일)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.39(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.76(dd, J=5.4, 1.5Hz, 1H), 8.51(ddd, J=8.1, 7.5, 1.5Hz, 1H), 8.39(d, J=7.5Hz, 1H), 7.85(dd, J=8.1, 5.4Hz, 1H), 7.61(d, J=3.6Hz, 1H), 7.08(d, J=3.6Hz, 1H), 4.63(s, 2H), 4. 00(dd, J=7.8, 4.5Hz, 1H), 3.98-3.81(m, 2H), 3.65-3.55(m, 2H), 3.49(t, J=8.1Hz, 2H), 2.72-2.55(m, 2H), 2.28-2.10(m, 2H), 1.90-1.27(m, 7H), 1.00-0.89(m, 9H).
실시예 24(94)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(피리딘-3-일)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.45(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 9.34(d, J=1.8Hz, 1H), 8.94(dd, J=8.1, 1.8Hz, 1H), 8.75(d, J=5.4Hz, 1H), 8.10(dd, J=8.1, 5.4Hz, 1H), 7.34(d, J=3.6Hz, 1H), 6.98(d, J=3.6Hz, 1H), 4.57(s, 2H), 4.00(dd, J=7.8, 4.5Hz, 1H), 3.98-3.77(m, 2H), 3.63-3.43(m, 4H), 2.73-2.55(m, 2H), 2.28-2.09(m, 2H), 1.89-1.27(m, 7H), 1.00-0.89(m, 9H).
실시예 24(95)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(3,5-디메틸피라졸-1-일)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.52(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.94(d, J=8.1Hz, 2H), 7.71(d, J=8.1Hz, 2H), 6.51(s, 1H), 4.49(s, 2H), 4.01(dd, J=7.8, 4.5Hz, 1H), 3.85-3.76(m, 2H), 3.58-3.48(m, 4H), 2.72-2.58(m, 2H), 2.45(s, 3H), 2.39(s, 3H), 2.23-2.06(m, 2H), 1.88-1.45(m, 5H), 1.45-1.34(m, 2H), 0.97-0.92(m, 9H).
실시예 24(96)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(5-클로로피리딘-3-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.57(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.54(bs, 1H), 8.45(bs, 1H), 7.87(bs, 1H), 7.71(d, J=8.4Hz, 2H), 7.26(d, J=8.4Hz, 2H), 4.39(s, 2H), 4.01(dd, J=7.8, 4.8Hz, 1H), 3.90-3.73(m, 2H), 3.56-3.40(m, 4H), 2.64-2.46(m, 2H), 2.24-2.09(m, 2H), 1.86-1.42(m, 5H), 1.42-1.30(m, 2H), 0.97-0.92(m, 9H).
실시예 24(97)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(피리미딘-2-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.61(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.62(d, J=4.8Hz, 2H), 7.68(d, J=8.4Hz, 2H), 7.32(d, J=8.4Hz, 2H), 7.26(t, J=4.8Hz, 1H), 4.40(s, 2H), 4.02(dd, J=7.5, 4.5Hz, 1H), 3.93-3.72(m, 2H), 3.60-3.35(m, 4H), 2.58-2.40(m, 2H), 2.28-2.07(m, 2H), 1.90-1.45(m, 5H), 1.45-1.36(m, 2H), 0.98-0.90(m, 9H).
실시예 24(98)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(피리딘-3-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.61(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.76(d, J=2.7Hz, 1H), 8.63(d, J=5.7Hz, 1H), 8.28(dd,J=8.7, 2.7Hz, 1H), 8.07(dd, J=8.7, 5.7Hz, 1H), 7.78(d, J=8.4Hz, 2H), 7.35(d, J=8.4Hz, 2H), 4.41(s, 2H), 4.02(dd, J=7.8, 4.5Hz, 1H), 3.93-3.72(m, 2H), 3.58-3.40(m, 4H), 2.68-2.48(m, 2H), 2.26-2.06(m, 2H), 1.90-1.46(m, 5H), 1.46-1.30(m, 2H), 0.98-0.91(m, 9H).
실시예 24(99)
1-(2-부티닐)-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-메틸페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.28(클로로포름:메탄올=19:1);
NMR(CD3OD): δ 7.39-7.29(m, 4H), 4.31(s, 2H), 4.27-4.20(m, 2H), 4.06(dd, J=7.5, 4.8Hz, 1H), 3.84(m, 2H), 3.62(m, 2H), 2.59(m, 2H), 2.42(s, 3H), 2.37(s, 3H), 2.34(s, 3H), 2.28(m, 2H), 1.92-1.60(m, 6H), 0.96(d, J=6.3Hz, 3H), 0.95(d, J=6.3Hz, 3H).
실시예 24(100)
(3R)-1-(2-부티닐)-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.29(클로로포름:메탄올=19:1);
NMR(CD3OD): δ 7.59-7.43(m, 5H), 4.31(s, 2H), 4.25(q, J=2.1Hz, 2H), 4.09(dd, J=7.2, 4.8Hz, 1H), 3.85(dt, J=3.0, 12.3Hz, 2H), 3.68-3.56(m, 2H), 2.61(m, 2H), 2.38(s, 3H), 2.37(s, 3H), 2.26(m, 2H), 1.83-1.43(m, 8H), 1.75(t, J=2.1Hz, 3H), 1.38-1.12(m, 3H), 0.96(m, 2H).
실시예 24(101)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-히드록시페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.46(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.47(d, J=9.0Hz, 2H), 6.97(d, J=9.0Hz, 2H), 6.88(d,J=9.0Hz, 2H), 6.80(d, J=9.0Hz, 2H), 4.30(s, 2H), 4.00(dd, J=7.5, 4.8Hz, 1H), 3.86-3.70(m, 2H), 3.52-3.34(m, 4H), 2.48-2.3 0(m, 2H), 2.28-2.10(m, 2H), 1.88-1.44(m, 5H), 1.44-1.28(m, 2H), 0.97-0.92(m, 9H).
실시예 24(102)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(피리딘-2-일)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.50(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.89(d, J=7.8Hz, 1H), 8.70(t, J=7.8Hz, 1H), 8.43(d, J=8.4Hz, 1H), 8.10-8.06(m, 3H), 7.98(d, J=8.7Hz, 2H), 4.51(s, 2H), 4.01(dd, J=7.8, 4.8Hz, 1H), 3.96-3.78(m, 2H), 3.56-3.45(m, 4H), 2.72-2.58(m, 2H), 2.24-2.08(m, 2H), 1.84-1.44(m, 5H), 1.44-1.34(m, 2H), 0.97-0.92(m, 9H).
실시예 24(103)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(피리딘-3-일)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.47(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 9.24(s, 1H), 8.98(d, J=8.4Hz, 1H), 8.88(d, J=8.4Hz, 1H), 8.21(dd, J=8.4, 5.7Hz, 1H), 7.96(d, J=8.4Hz, 2H), 7.87(d, J=8.4Hz, 2H), 4.47(s, 2H), 4.01(dd, J=7.5, 4.8Hz, 1H), 3.96-3.75(m, 2H), 3.58-3.44(m, 4H), 2.64-2.50(m, 2H), 2.25-2.08(m, 2H), 1.88-1.48(m, 5H), 1.48-1.32(m, 2H), 0.97-0.92(m, 9H).
실시예 24(104)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-카르복시페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.27(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.19(d, J=8.4Hz, 2H), 7.61(d, J=8.4Hz, 2H), 4.32(s, 2H), 4.03(dd, J=7.5, 4.5Hz, 1H), 3.96-3.74(m, 2H), 3.66-3.55(m, 2H), 3.48-3.36(m, 2H), 2.58-2.40(m, 2H), 2.45(s, 3H), 2.40(s, 3H), 2.32-2.14(m, 2H), 1.90-1.46(m, 5H), 1.46-1.30(m, 2H), 0.99-0.95(m, 9H).
실시예 24(105)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(피라진-2-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.48(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 8.47(d, J=1.5Hz, 1H), 8.32(d, J=2.7Hz, 1H), 8.13(dd, J=2.7, 1.5Hz, 1H), 7.65(d, J=8.4Hz, 2H), 7.32(d, J=8.4Hz, 2H), 4.40(s, 2H), 4.02(dd, J=7.5, 4.5Hz, 1H), 3.94-3.73(m, 2H), 3.58-3.46(m, 2H), 3.44-3.34(m, 2H), 2.52-2.34(m, 2H), 2.30-2.10(m, 2H), 1.90-1.43(m, 5H), 1.43-1.26(m, 2H), 0.99-0.90(m, 9H).
실시예 24(106)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-카르복시페닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.20(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.11(d, J=8.4Hz, 2H), 7.83(d, J=8.4Hz, 2H), 7.77(d, J=8.4Hz, 2H), 7.69(d, J=8.4Hz, 2H), 4.43(s, 2H), 4.01(dd, J=7.8, 4.5Hz, 1H), 3.96-3.74(m, 2H), 3.58-3.36(m, 4H), 2.55-2.3 8(m, 2H), 2.28-2.10(m, 2H), 1.88-1.44(m, 5H), 1.44-1.30(m, 2H), 0.97-0.92(m, 9H).
실시예 24(107)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(피리딘-4-일)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.50(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.91(d, J=6.9Hz, 2H), 8.45(d, J=6.9Hz, 2H), 8.11(d, J=7.8Hz, 2H), 7.91(d, J=7.8Hz, 2H), 4.49(s, 2H), 4.01(dd, J=7.8, 4.8Hz, 1H), 3.96-3.78(m, 2H), 3.58-3.40(m, 4H), 2.64-2.48(m, 2H), 2.26-2.08(m, 2H), 1.90-1.28(m, 7H), 0.96-0.93(m, 9H).
실시예 24(108)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(피리딘-2-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.46(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.44-8.15(m, 2H), 7.82(d, J=7.2Hz, 2H), 7.60-7.40(m, 1H), 7.42(d, J=7.2Hz, 2H), 7.27-7.24(m, 1H), 4.43(s, 2H), 4.02(dd, J=7.5, 4.5Hz, 1H), 3.92-3.70(m, 2H), 3.58-3.40(m, 4H), 2.6 4-2.42(m, 2H), 2.28-2.06(m, 2H), 1.92-1.28(m, 7H), 0.97-0.94(m, 9H).
실시예 24(109)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(나프탈렌-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.71(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.08-7.93(m, 4H), 7.64-7.57(m, 3H), 4.54(s, 2H), 4.04(dd, J=7.5, 4.8Hz, 1H), 3.96-3.80(m, 2H), 3.60-3.44(m, 2H), 3.42-3.36(m, 2H), 2.42-2.08(m, 4H), 1.82-1.16(m, 15H), 0.95(t, J=7.5Hz, 3H), 0.95(m, 2H).
실시예 24(110)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(6-메톡시나프탈렌-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.75(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.98(s, 1H), 7.91(d, J=8.7Hz, 1H), 7.85(d, J=8.7Hz, 1H),7.58(d, J=8.7Hz, 1H), 7.31(d, J=2.4Hz, 1H), 7.22(dd, J=8.7, 2.4Hz, 1H), 4.48(s, 2H), 4.04(dd, J=7.8, 4.8Hz, 1H), 3.94-3.78(m, 2H), 3.93(s, 3H), 3.58-3.44(m, 2H), 3.42-3.36(m, 2H), 2.48-2.30(m, 2H), 2.24-2.08(m, 2H), 1.82-1.10(m, 15H), 0.95(t, J=7.2Hz, 3H), 0.95(m, 2H).
실시예 24(111)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-카르복시페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.27(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.03(d, J=8.7Hz, 2H), 7.63(d, J=8.4Hz, 2H), 7.17(d, J=8.4Hz, 2H), 7.07(d, J=8.7Hz, 2H), 4.37(s, 2H), 4.01(dd, J=7.5, 4.5Hz, 1H), 3.90-3.70(m, 2H), 3.56-3.36(m, 4H), 2.56-2.3 8(m, 2H), 2.25-2.10(m, 2H), 1.84-1.44(m, 5H), 1.44-1.39(m, 2H), 0.98-0.93(m, 9H).
실시예 24(112)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(피리딘-4-일)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.39(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.80(d, J=6.9Hz, 2H), 8.39(d, J=6.9Hz, 2H), 7.69(d, J=3.6Hz, 1H), 7.08(d, J=3.6Hz, 1H), 4.62(s, 2H), 4.00(dd, J=7.8, 4.5,Hz, 1H), 3.99-3.79(m, 2H), 3.65-3.43(m, 4H), 2.72-2. 54(m, 2H), 2.30-2.10(m, 2H), 1.88-1.26(m, 7H), 1.00-0.84(m, 9H).
실시예 24(113)
1-부틸-2,5-디옥소-3-시클로펜틸메틸-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.66(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.52(d, J=8.5Hz, 2H), 7.40(t, J=7.5Hz, 2H), 7.18(t,J=7.5Hz, 1H), 7.05(m, 4H), 4.34(s, 2H), 4.00(t, J=6.0Hz, 1H), 3.82(m, 2H), 3.49(m, 2H), 3.39(m, 2H), 2.37(m, 2H), 2.17(m, 2H), 1.96(m, 1H), 1.81(m, 4H), 1.58(m, 6H), 1.38(m, 2H), 1.17(m, 2H), 0.95(t, J=7.0Hz, 3H).
실시예 24(114)
(3R)-1-부틸-2,5-디옥소-3-(2,2-디메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.52(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.52(d, J=9.0Hz, 2H), 7.40(t, J=7.5Hz, 2H), 7.18(t, J=7.5Hz, 1H), 7.04(m, 4H), 4.33(s, 2H), 4.01(dd, J=7.2, 3.3Hz, 1H), 3.82(m, 1H), 3.71(m, 1H), 3.50(m, 2H), 3.43(m, 2H), 2.38(m, 2H), 2.24(m, 2H), 2.00(dd, J=14.0, 3.3Hz, 1H), 1.55(dd, J=14.0, 7.2Hz, 1H), 1.50(m, 2H), 1.36(m, 2H), 0.99(s, 9H), 0.95(t, J=7.0Hz, 3H).
실시예 24(115)
(3S)-1-부틸-2,5-디옥소-3-(2,2-디메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.52(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.52(d, J=9.0Hz, 2H), 7.40(t, J=7.5Hz, 2H), 7.18(t, J=7.5Hz, 1H), 7.04(m, 4H), 4.33(s, 2H), 4.01(dd, J=7.2, 3.3Hz, 1H), 3.82(m, 1H), 3.71(m, 1H), 3.50(m, 2H), 3.43(m, 2H), 2.38(m, 2H), 2.24(m, 2H), 2.00(dd, J=14.0, 3.3Hz, 1H), 1.55(dd, J=14.0, 7.2Hz, 1H), 1.50(m, 2H), 1.36(m, 2H), 0.99(s, 9H), 0.95(t, J=7.0Hz, 3H).
실시예 24(116)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-니트로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.68(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.33(d, J=8.7Hz, 2H), 7.78(d, J=8.7Hz, 2H), 4.49(s, 2H), 4.03(dd, J=7.5, 4.5Hz, 1H), 3.93-3.76(m, 2H), 3.55-3.43(m, 2H), 3.40-3.31(m, 2H), 2.45-2.28(m, 2H), 2.27-2.08(m, 2H), 1.83-1.14(m, 15H), 1.04-0.86(m, 5H).
실시예 24(117)
(3R)-1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-페닐메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.55(클로로포름:메탄올=10:1);
NMR(CDCl3):δ 7.38-7.14(m, 10H), 6.00-5.75(m, 1H), 4.40-4.15(m, 2H), 3.92-3.58(m, 3H), 3.58-2.25(m, 13H), 2.18-1.45(m, 10H).
실시예 24(118)
(3S)-1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-페닐메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.55(클로로포름:메탄올=10:1);
NMR(CDCl3):δ 7.40-7.15(m, 10H), 6.05-5.80(m, 1H), 4.40-4.10(m, 2H), 3.90-3.55(m, 3H), 3.55-2.20(m, 13H), 2.18-1.45(m, 10H).
실시예 24(119)
(3S)-1-프로필-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.32(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.40-7.20(m, 10H), 5.06(s, 2H), 4.09(dd, J=5.2, 4.6Hz, 1H), 4.00-3.70(m, 2H), 3.70-3.55(m, 2H), 3.50-3.30(m, 4H), 3.20-3.00(m, 4H),2.65-2.35(m, 2H), 2.30-2.10(m, 2H), 2.00-1.75(m, 2H), 1.70-1.40(m, 4H), 0.96(t, J=7.4Hz, 3H).
실시예 25
1-부틸-2,5-디옥소-3-(카르복시메틸)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
실시예 24(11)에서 제조한 화합물(173 mg)의 메탄올(5 mL) 용액에 2N 수산화 나트륨 수용액(2 ml)을 첨가하였다. 반응 혼합물을 실온에서 3시간 교반하였다. 반응 혼합물에 2N 염산 수용액을 pH가 4가 될 때까지 첨가하고 초산에틸로 추출하였다. 추출물을 포화염화나트륨 수용액으로 세정하고, 무수 황산나트륨으로 건조시켜 농축하였다. 얻어진 잔류물을 1,4-디옥산에 용해하여 4N 염산·1,4-디옥산 용액을 첨가하였다. 반응 혼합물을 농축하여 얻어진 잔류물을 디에틸에테르로 세정하고, 건조시켜 이하의 물성치를 갖는 본 발명 화합물(127 mg)을 얻었다.
TLC: Rf 0.51(클로로포름:메탄올:초산=20:4:1);
NMR(CD3OD):7.55-7.53(m, 2H), 7.42-7.36(m, 2H), 7.20-7.15(m, 1H), 7.07-7.02(m, 4H), 4.33(s, 2H), 4.27(t, J=4.5Hz, 1H), 3.96-3.90(m, 1H), 3.72-3.66(m, 1H), 3.54-3.38(m, 4H), 2.97(dd, J=18.0, 4.8 H z, 1H), 2.79(dd, J=18.0, 4.8Hz, 1H), 2.50-2.36(m, 3H), 2.27-2.16(m, 1H), 1.62-1.48(m, 2H), 1.41-1.30(m, 2H), 0.94(t, J=7.2Hz, 3H).
실시예 26(1)∼26(3)
참고예 2에서 제조한 수지(3) 및 N-알릴옥시카르보닐-4-피페리돈을 이용하고, n-프로필아민 및 N-(t-부틸옥시카르보닐)류신 대신에 각각 해당하는 화합물을 이용하여 참고예 3→참고예 4와 동일한 조작을 하고, 또한 3,5-디메틸-1-페닐-4-포르밀피라졸 대신에 해당하는 화합물을 이용하여 참고예 5→참고예 6→실시예 1과 동일한 조작을 하며, 또한 수산기가 일부 아세틸화되었기 때문에, 실시예 25와 동일한 조작을 하여 이하의 본 발명 화합물을 얻었다.
실시예 26(1)
1-(3-히드록시부틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.49(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.54(d, J=8.5Hz, 2H), 7.39(t, J=7.5Hz, 2H), 7.18(t,J=7.5Hz, 1H), 7.04(m, 4H), 4.33(s, 2H), 4.02(m, 1H), 3.80(m, 3H), 3.51(m, 4H), 2.46(m, 2H), 2.19(m, 2H), 1.85-1.57(m, 5H), 1. 17(d, J=6.0Hz, 3H), 0.94(d, J=9.0Hz, 6H).
실시예 26(2)
1-(3-히드록시프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.46(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.51(d, J=8.5Hz, 2H), 7.40(t, J=7.5Hz, 2H), 7.18(t, J=7.5Hz, 1H), 7.04(m, 4H), 4.34(s, 2H), 4.02(dd, J=7.5, 4.0Hz, 1H), 3.80(m, 2H), 3.60(t, J=6.0Hz, 2H), 3.48(m, 4H), 2.40(m, 2H), 2.20(m, 2H), 1.82-1.58(m, 5H), 0.94(d, J=6.0Hz, 3H), 0.93(d, J=6.0Hz, 3H).
실시예 26(3)
1-(2-히드록시부틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.49(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.50(d, J=8.7Hz, 2H), 7.39(dd, J=8.7, 7.5Hz, 2H), 7.18(t, J=7.5Hz, 1H), 7.10-7.00(m, 4H), 4.32(s, 2H), 4.03(dd, J=8.1, 4.8Hz, 1H), 3.96-3.41(m, 6H), 3.27-3.14(m, 1H), 2.68-2.53(m, 1H), 2.37-2.26(m, 3H), 1.94-1.24(m, 5H), 1.08-0.82(m, 9H).
실시예 27
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-아미노페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
실시예 24(116)에서 제조한 화합물(50 mg)의 메탄올 용액에 아르곤 분위하에 5% 팔라듐-탄소(10 mg)를 첨가하였다. 반응 혼합물을 수소 가스 분위기하에 실온에서 20분간 교반하였다. 반응 혼합물을 세라이트(상품명)를 통해 여과하고, 여과액을 농축하였다. 잔류물을 실리카겔 칼럼 크로마토그래피(클로로포름:메탄올 = 50:1→30:1→20:1)에 의해 정제하였다. 얻어진 화합물을 메탄올에 용해하고 4N 염산/초산에틸 용액을 첨가하여 농축하였다. 얻어진 잔류물을 디에틸에테르로 세정하고, 건조시켜 이하의 물성치를 갖는 본 발명 화합물(34 mg)을 얻었다.
TLC: Rf 0.21(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.80(d, J=8.4Hz, 2H), 7.47(d, J=8.4Hz, 2H), 4.41(s, 2H), 4.03(dd, J=7.5, 4.5Hz, 1H), 3.86-3.74(m, 2H), 3.52-3.45(m, 4H), 2.65-2.52(m, 2H), 2.24-2.08(m, 2H), 1.80-1.16(m, 15H), 0.94(t, J=7.5Hz, 3H), 0.94(m, 2H).
실시예 28
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-((4-메틸페닐)설포닐아미노)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
실시예 28에서 제조한 화합물(33 mg)의 피리딘(2 ml) 용액에 p-톨루엔설포닐클로라이드(21 mg)를 첨가하였다. 반응 혼합물을 실온에서 27시간 교반하였다. 반응 혼합물을 농축하고, 포화탄산수소나트륨 수용액을 첨가하여 초산에틸로 추출하였다. 추출물을 포화염화나트륨 수용액으로 세정하고, 무수 황산나트륨으로 건조시켜 농축하였다. 잔류물을 실리카겔 칼럼 크로마토그래피(클로로포름:메탄올=10:1)에 의해 정제하였다. 얻어진 화합물을 메탄올에 용해하고, 4N 염산/초산에틸 용액을 첨가하여 농축하였다. 얻어진 잔류물을 디에틸에테르로 세정하고, 건조시켜 이하의 물성치를 갖는 본 발명 화합물(27 mg)을 얻었다.
TLC: Rf 0.63(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.70(d, J=8.4Hz, 2H), 7.41(d, J=8.4Hz, 2H), 7.30(d, J=8.4Hz, 2H), 7.22(d, J=8.4Hz, 2H), 4.25(s, 2H), 4.03(dd, J=7.2, 4.5Hz, 1H), 3.78(m, 2H), 3.42(m, 4H), 2.42-2.06(m, 4H), 2.37(s, 3H), 1.82-1.10(m, 15H), 0.95(t, J=7.2Hz, 3H), 0.95(m, 2H).
실시예 28(1)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(페닐카르보닐아미노)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
p-톨루엔설포닐클로라이드 대신에 벤조일클로라이드를 이용하여 실시예 28과 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.43(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.93(d, J=8.4Hz, 2H), 7.88(d, J=8.4Hz, 2H), 7.61-7.50(m, 5H), 4.34(s, 2H), 4.05(dd, J=7.8, 4.5Hz, 1H), 3.80(m, 2H), 3.42(m, 4H), 2.24(m, 4H), 1.82-1.16(m, 15H), 0.96(t, J=7.2Hz, 3H), 0.96(m, 2H).
실시예 29
(3S)-1-부틸-2,5-디옥소-3-벤질옥시메틸-9-벤질옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸
참고예 2에서 제조한 수지(3) 및 N-벤질옥시카르보닐-4-피페리돈, O-벤질-N-(t-부틸옥시카르보닐)-L-세린을 이용하여 참고예 3→참고예 6→실시예 1과 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.66(클로로포름:메탄올=20:1);
NMR(CDCl3): δ 7.40-7.25(m, 10H), 6.09(brs, 1H), 5.15(s, 2H), 4.54(s, 2H), 4.20-3.98(br, 2H), 4.18(dd, J=8.4, 3.6Hz, 1H), 3.93(dd, J=9.3, 3.6Hz, 1H), 3.80-3.56(br, 1H), 3.66(dd, J=9.3, 8.4,Hz, 1H), 3.45-3.12(m, 3H), 2.02-1.75(m, 4H), 1.57-1.39(m, 2H), 1.38-1.20(m, 2H), 0.91(t, J=7.2Hz, 3H).
실시예 30
(3S)-1-부틸-2,5-디옥소-3-히드록시메틸-9-벤질옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸
실시예 29에서 제조한 화합물(245 mg)의 디클로로메탄(5 ml) 용액에 -40℃에서 3브롬화붕소의 1M 디클로로메탄 용액(1.4 ml)을 첨가하고 -20℃에서 3시간 교반하였다. 반응 혼합물에 물과 포화탄산수소나트륨 수용액을 첨가하고 초산에틸로 추출하였다. 추출물을 물, 포화염화나트륨 수용액으로 세정하고, 무수 황산나트륨으로 건조시켜 농축하였다. 잔류물을 실리카겔 칼럼 크로마토그래피(클로로포름:메탄올=30:1)에 의해 정제하여 이하의 물성치를 갖는 본 발명 화합물(173 mg)을 얻었다.
TLC: Rf 0.29(클로로포름:메탄올=20:1);
NMR(CDCl3): δ 7.42-7.27(m, 5H), 6.26-6.15(br, 1H), 5.16(s, 2H), 4.26-4.00(m, 2H), 3.98-3.82(m, 2H), 3.84-3.60(br, 1H), 3.43-3.13(m, 4H), 2.80-2.68(br, 1H), 2.05-1.75(m, 4H), 1.58-1.40(m, 2H), 1.40-1.20(m, 2H), 0.92(t,J=7.5Hz, 3H).
실시예 31
(3S)-1-부틸-2,5-디옥소-3-히드록시메틸-1,4,9-트리아자스피로[5.5]운데칸
실시예 30에서 제조한 화합물을 이용하여 실시예 9와 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.21(클로로포름:메탄올:초산=20:4:1);
NMR(d6-DMSO): δ 7.83(brs, 1H), 5.10-4.90(br, 1H), 3.88-3.78(m, 1H), 3.76-3.65(m, 1H), 3.58-3.48(m, 1H), 3.28-3.18(m, 1H), 3.18-3.04(m, 3H), 2.88-2.75(m, 2H), 1.94-1.83(m, 1H), 1.83-1.64(m, 3H), 1.56-1.42(m, 1H), 1.42-1.20(m, 3H), 0.88(t, J=7.2Hz, 3H).
실시예 32(1)
(3S)-1-부틸-2,5-디옥소-3-히드록시메틸-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
4-페닐옥시벤즈알데히드와 실시예 31에서 제조한 화합물을 이용하여 실시예 10과 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.49(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.52(d, J=8.7Hz, 2H), 7.43-7.35(m, 2H), 7.22-7.14(m, 1H), 7.06(d, J=8.7Hz, 2H), 7.06-7.00(m, 2H), 4.33(s, 2H), 4.03-3.90(m, 3H), 3.79-3.66(m, 1H), 3.65(dd, J=10.5, 2.4Hz, 1H), 3.61-3.42(m, 3H), 3.30-3.18(m, 1H), 2.50-2.24(m, 3H), 2.24-2.12(m, 1H), 1.76-1.58(m, 1H), 1.54-1.26(m, 3H), 0.95(t, J=7.5Hz, 3H).
실시예 32(2)
(3S)-1-부틸-2,5-디옥소-3-히드록시메틸-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
1-페닐-3,5-디메틸-4-포르밀피라졸과 실시예 31에서 제조한 화합물을 이용하여 실시예 10과 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.47(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.61-7.46(m, 5H), 4.32(s, 2H), 4.08-3.92(m, 3H), 3.83-3.70(m, 1H), 3.66(dd, J=10.5, 2.4Hz, 1H), 3.66-3.52(m, 3H), 3.40-3.25(m, 1H), 2.64-2.50(m, 1H), 2.50-2.40(m, 2H), 2.41(s, 3H), 2.39(s, 3H), 2.28-2.15(m, 1H), 1.80-1.58(m, 1H), 1.58-1.30(m, 3H), 0.96(t, J=7.5Hz, 3H).
참고예 11: 화합물(7)의 합성
참고예 2에서 제조한 수지(3) 및 N-알릴옥시카르보닐-4-피페리돈, n-부틸아민 및 N-(t-부틸옥시카르보닐)류신을 이용하여 참고예 3→참고예 4와 동일한 조작을 하고, 또한 3,5-디메틸-1-페닐-4-포르밀피라졸 대신에 4-히드록시벤즈알데히드를 이용하여 참고예 5와 동일한 조작을 하여 화합물(7)을 얻었다.
참고예 12: 화합물(8)의 합성
참고예 11에서 제조한 화합물(60 mg)의 디클로로메탄(2 ml) 현탁액에 트리페닐포스핀(80 mg)과 1M의 시클로펜타놀의 디클로로메탄 용액(0.302 ml)과 디에틸아조디카르복실레이트(0.137 ml)를 첨가하였다. 반응 혼합물을 실온에서 18시간 교반하였다. 반응액을 여과하여 얻어진 수지를 디클로로메탄(2 ml×4회), 메탄올(2 ml×3회), 디클로로메탄(3 ml×4회)으로 세정하여 화합물(8)을 얻었다.
실시예 33
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-시클로펜틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
참고예 12에서 제조한 화합물을 이용하여 참고예 6→실시예 1과 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.49(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.41(d, J=8.7Hz, 2H), 6.98(d, J=8.7Hz, 2H), 4.83(m, 1H), 4.25(brs, 2H), 4.00(dd, J=7.8, 4.5Hz, 1H), 3.86-3.65(m, 2H), 3.53-3.27(m, 4H), 2.40-2.06(m, 4H), 2.02-1.43(m, 13H), 1.43-1.24(m, 2H), 1.01-0.90(m, 9H).
실시예 33(1)∼33(6)
n-부틸아민 및 N-(t-부틸옥시카르보닐)류신 대신에 해당하는 화합물을 이용하여 참고예 11과 동일한 조작을 하고, 시클로펜타놀 대신에 해당하는 화합물을 이용하여 참고예 12→실시예 33과 동일한 조작을 하여 이하에 도시한 본 발명 화합물을 얻었다.
실시예 33(1)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(2-디에틸아미노에틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.54(클로로포름:메탄올:28% 암모니아수=80:10:1);
NMR(CD3OD): δ 7.57(d, J=8.7Hz, 2H), 7.12(d, J=8.7Hz, 2H), 4.40(t, J=4.8Hz, 2H), 4.30(s, 2H), 4.03(dd, J=7.5, 5.1Hz, 1H), 3.84-3.67(m, 2H), 3.63(t, J=4.8Hz, 2H), 3.50-3.40(m, 4H), 3.40-3.31(m, 4H), 2.58-2.41(m, 2H), 2.23-2.04(m, 2H), 1.82-1.42(m, 10H), 1.41-1.12(m, 11H), 1.04-0.87(m, 5H).
실시예 33(2)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(2-디메틸아미노에틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.46(클로로포름:메탄올:28% 암모니아수=80:10:1);
NMR(CD3OD): δ 7.57(d, J=8.7Hz, 2H), 7.13(d, J=8.7Hz, 2H), 4.39(t, J=4.8Hz, 2H), 4.30(s, 2H), 4.02(dd, J=7.5, 4.5Hz, 1H), 3.84-3.67(m, 2H), 3.61(t, J=4.8Hz, 2H), 3.50-3.38(m, 4H), 2.98(s, 6H), 2.59-2.42(m, 2H), 2.24-2.03(m, 2H), 1.83-1.12(m, 15H), 1.04-0.86(m, 5H).
실시예 33(3)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-프로필옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.59(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.43(d, J=8.7Hz, 2H), 7.01(d, J=8.7Hz, 2H), 4.27(brs, 2H), 4.03(dd, J=7.5, 4.5Hz, 1H), 3.96(t, J=6.6Hz, 2H), 3.85-3.67(m, 2H), 3.53-3.33(m, 4H), 2.45-2.27(m, 2H), 2.26-2.07(m, 2H), 1.86-1.14(m, 17H), 1.03(t, J=7.2Hz, 3H), 1.00-0.89(m, 5H).
실시예 33(4)
1-(티오펜-2-일메틸)-2,5-디옥소-3-시클로헥실메틸-9-(4-시클로프로필메틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.61(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.42(d, J=8.7Hz, 2H), 7.27(dd, J=5.4, 0.9Hz, 1H), 7.06-6.97(m, 3H), 6.91(dd, J=5.4, 3.6Hz, 1H), 4.95-4.85(m, 2H), 4.27(brs, 2H), 4.14(dd, J=7.5, 4.5Hz, 1H), 3.84(d, J=6.6Hz, 2H), 3.84-3.66(m, 2H), 3.51-3.39(m, 2H), 2.59-2.36(m, 2H), 2.24-2.07(m, 2H), 1.84-1.44(m, 8H), 1.35-1.12(m, 4H), 1.04-0.85(m, 2H), 0.66-0.57(m, 2H), 0.38-0.31(m, 2H).
실시예 33(5)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-시클로프로필메틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.61(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.42(d, J=8.4Hz, 2H), 7.01(d, J=8.4Hz, 2H), 4.26(brs, 2H), 4.03(dd, J=7.8, 4.8Hz, 1H), 3.84(d, J=6.9Hz, 2H), 3.83-3.66(m, 2H), 3.51-3.33(m, 4H), 2.44-2.26(m, 2H), 2.25-2.06(m, 2H), 1.82-1.12(m, 16H), 1.04-0.86(m, 5H), 0.66-0.57(m, 2H), 0.38-0.31(m, 2H).
실시예 33(6)
1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-시클로프로필메틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.55(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.42(d, J=8.7Hz, 2H), 7.01(d, J=8.7Hz, 2H), 4.26(brs, 2H), 4.00(dd, J=7.8, 4.5Hz, 1H), 3.84(d, J=6.9Hz, 2H), 3.84-3.66(m, 2H), 3.50-3.33(m, 4H), 2.43-2.26(m, 2H), 2.26-2.08(m, 2H), 1.89-1.43(m, 5H), 1.43-1.17(m, 3H), 1.00-0.88(m, 9H), 0.66-0.58(m, 2H), 0.38-0.31(m, 2H).
실시예 34
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(디메틸아미노)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
4-디메틸아미노벤즈알데히드와 실시예 9(1)에서 제조한 화합물을 이용하여 실시예 10과 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.26(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.78(d, J=8.7Hz, 2H), 7.59(d, J=8.7Hz, 2H), 4.39(s, 2H), 4.03(dd, J=7.5, 4.8,Hz, 1H), 3.90-3.70(m, 2H), 3.52-3.40(m, 4H), 3.26(s, 6H), 2.64-2.47(m, 2H), 2.24-2.04(m, 2H), 1.82-1. 12(m, 15H), 1.04-0.88(m, 5H).
실시예 34(1)
1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(디에틸아미노)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
4-디메틸아미노벤즈알데히드 대신에 4-디에틸아미노벤즈알데히드를 이용하여 실시예 34와 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.28(클로로포름:메탄올:초산=10:1);
NMR(CD3OD): δ 7.94-7.78(m, 2H), 7.72-7.52(m, 2H), 4.43(s, 2H), 4.03(dd, J=7.5, 4.8,Hz, 1H), 3.92-3.73(m, 2H), 3.73-3.60(m, 4H), 3.54-3.40(m, 4H), 2.63-2.45(m, 2H), 2.25-2.05(m, 2H), 1.82-1.10(m, 21H), 1.04-0.86(m, 5H).
실시예 35
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-벤질옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸
참고예 2에서 제조한 수지(3), N-벤질옥시카르보닐-4-피페리돈, n-부틸아민, N-(t-부틸옥시카르보닐)-L-류신을 이용하여 참고예 3→참고예 6→실시예 1과 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.67(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.35(m, 5H), 6.50(brs, 1H), 5.15(s, 2H), 4.08(m, 2H), 3.96(m, 1H), 3.62(brs, 1H), 3.44(brs, 1H), 3.26(m, 2H), 1.95-1.76(m, 4H),1.61-1.45(m, 5H), 1.31(m, 2H), 0.96(d, J=6.3Hz, 3H), 0.93(d, J=6.3Hz, 3H), 0.91(t, J=7.2Hz, 3H).
실시예 36
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸·염산염
실시예 35에서 제조한 화합물을 이용하여 실시예 9와 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.18(클로로포름:메탄올=4:1);
NMR(CD3OD): δ 4.02(dd, J=7.8, 4.6Hz, 1H), 3.80(dd, J=12.5, 4.0Hz, 1H), 3.72(dd, J=12.5, 4.0Hz, 1H), 3.39(m, 4H), 2.34-2.09(m, 4H), 1.88-1.50(m, 5H), 1.37(m, 2H), 0.96(t, J=7.5Hz, 3H), 0.95(d, J=6.5Hz, 3H), 0.94(d, J=6.5Hz, 3H).
실시예 37(1)∼37(88)
실시예 36에서 제조한 화합물과 해당하는 알데히드 화합물을 이용하여 실시예 10과 동일한 조작을 하여 이하에 도시한 본 발명 화합물을 얻었다.
실시예 37(1)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(3-메틸-4-클로로페닐)-1-(4-메틸페닐메틸)피라졸-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.46(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.42(d, J=8.1Hz, 1H), 7.28(d, J=1.5Hz, 1H), 7.19(dd, J=8.1, 1.5Hz, 1H), 7.11(d, J=8.1Hz, 2H), 6.92(d, J=8.1Hz, 2H), 6.65(s, 1H), 5.35(s, 2H), 4.40(s, 2H), 4.02(dd, J=7.5, 4.5Hz, 1H), 3.97-3.76(m, 2H), 3.64-3.52(m, 2H), 3.46-3.35(m, 2H), 2.56-2.38(m, 2H), 2.35(s, 3H), 2.28(s, 3H), 2.30-2.10(m, 2H), 1.91-1.46(m, 5H), 1.46-1.30(m, 2H), 0.96(t, J=6.9Hz, 3H), 0.95(d, J=6.3Hz, 6H).
실시예 37(2)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-디메틸아미노페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.47(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.78(d, J=8.7Hz, 2H), 7.58(d, J=8.7Hz, 2H), 4.40(s, 2H), 4.01(dd, J=7.8, 4.5Hz, 1H), 3.82(m, 2H), 3.42(m, 4H), 3.26(s, 6H), 2.56(m, 2H), 2.18(m, 2H), 1.88-1.30(m, 7H), 0.95(t, J=7.2Hz, 3H), 0.95(d, J=6.3Hz, 3H), 0.94(d, J=6.3Hz, 3H).
실시예 37(3)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-디에틸아미노페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.34(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.96-7.82(m, 2H), 7.74-7.55(m, 2H), 4.40(s, 2H),4.00(dd, J=7.5, 4.5Hz, 1H), 3.93-3.60(m, 6H), 3.55-3.40(m, 4H), 2.65-2.48(m, 2H), 2.25-2.06(m, 2H), 1.89-1.26(m, 7H), 1.15(t, J=7.2Hz, 6H), 1.00-0.87(m, 9H).
실시예 37(4)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-시클로헥실옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.61(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.45-7.42(m, 2H), 7.02-6.99(m, 2H), 4.40-4.31(m, 1H), 4.27(s, 2H), 4.00(dd, J=8.0, 4.5Hz, 1H), 3.83-3.70(m, 2H), 3.47(brd, 2H), 3.42-3.35(m, 2H), 2.43-2.32(m, 2H), 2.24-2.11(m, 2H), 2.00-1.93(m, 2H), 1.86-1.32(m, 15H), 0.97-0.92(m, 9H).
실시예 37(5)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-메틸페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.70(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.52-7.47(m, 2H), 7.22-7.19(m, 2H), 7.04-7.00(m, 2H), 6.94-6.90(m, 2H), 4.32(s, 2H), 4.01(dd, J=8.0, 4.5Hz, 1H), 3.86-3.73(m, 2H), 3.48(brd, 2H), 3.42-3.34(m, 2H), 2.45-2.33(m, 5H), 2.25-2.12(m, 2H), 1.85-1.48(m, 5H), 1.41-1.31(m, 2H), 0.97-0.92(m, 9H).
실시예 37(6)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-메톡시페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.65(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.49-7.46(m, 2H), 7.00-6.94(m, 6H), 4.31(s, 2H),4.01(dd, J=8.0, 4.5Hz, 1H), 3.84-3.71(m, 5H), 3.48(brd, 2H), 3.40-3.31(m, 2H), 2.42-2.30(m, 2H), 2.25-2.12(m, 2H), 1.83-1.48(m, 5H), 1.41-1.30(m, 2H), 0.97-0.92(m, 9H).
실시예 37(7)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-부틸페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.35(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.46(d, J=8.1Hz, 2H), 7.32(d, J=8.1Hz, 2H), 4.31(s, 2H), 4.01(dd, J=7.8, 4.5Hz, 1H), 3.84-3.68(m, 2H), 3.54-3.36(m, 4H), 2.67(t, J=7.8Hz, 2H), 2.48-2.30(m, 2H), 2.26-2.08(m, 2H), 1.90-1.28(m, 11H), 0.96(t, J=7.2Hz, 3H), 0.95(d, J=6.3Hz, 3H), 0.94(d, J=6.3Hz, 3H), 0.94(t, J=7.2Hz, 3H).
실시예 37(8)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(2-메틸프로필)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.38(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.47(d, J=6.9Hz, 2H),7.30(d, J=6.9Hz, 2H), 4.33(s, 2H), 4.01(dd, J=7.5, 4.5Hz, 1H), 3.90-3.70(m, 2H), 3.56-3.34(m, 4H), 2.53(d, J=7.2Hz, 2H), 2.53-2.30(m, 2H), 2.24-2.08(m, 2H), 1.96-1.26(m, 8H), 0.95(t, J=7.8Hz, 3H), 0.95(d, J=6.6Hz, 3H), 0.94(d, J=6.6Hz, 3H), 0.91(d, J=6.6Hz, 6H).
실시예 37(9)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-플루오로페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.36(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.53(d, J=8.4Hz, 2H), 7.17(d, J=8.4Hz, 2H), 7.16-7.04(m, 4H), 4.33(s, 2H), 4.02(dd, J=7.8, 4.8Hz, 1H), 3.88-3.68(m, 2H), 3.58-3.36(m, 4H), 2.46-2.10(m, 4H), 1.90-1.24(m, 7H), 0.96(t, J=6.9Hz, 3H), 0.95(d, J=6.6Hz, 3H), 0.94(d, J=6.6Hz, 3H).
실시예 37(10)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3-히드록시-4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.20(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.03-6.94(m, 3H), 4.23(s, 2H), 4.01(dd, J=7.8, 4.5Hz, 1H), 3.89(s, 3H), 3.84-3.68(m, 2H), 3.56-3.36(m, 4H), 2.42-2.08(m, 4H), 1.88-1.24(m, 7H), 0.96(t, J=7.2Hz, 3H), 0.95(d, J=6.3Hz, 3H), 0.94(d, J=6.3Hz, 3H).
실시예 37(11)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-플루오로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.48(헥산:초산에틸=1:1);
NMR(CD3OD): δ 7.64-7.54(m, 2H), 7.37-7.27(m, 2H), 4.45(s, 2H), 4.01(dd, J=7.5, 4.5Hz, 1H), 3.94-3.81(m, 2H), 3.54(m, 2H), 3.36(m, 2H), 2.38(m, 2H), 2.19(m, 2H), 1.82-1.49(m, 5H), 1.35(m, 2H), 0.95(t, J=7.5Hz, 3H), 0.94(d, J=6.5Hz, 3H), 0.93(d, J=6.5Hz, 3H).
실시예 37(12)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3-플루오로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.52(헥산:초산에틸=1:1);
NMR(CD3OD): δ 7.52(dt, J=8.3, 6.0Hz, 1H), 7.41-7.37(m, 2H), 7.26(t,J=8.3Hz, 1H), 4.39(s, 2H), 4.01(dd, J=7.5, 4.5Hz, 1H), 3.89-3.76(m, 2H), 3.50-3.38(m, 4H), 2.48-2.38(m, 2H), 2.25-2.12(m, 2H), 1.84-1.75(m, 1H), 1.72-1.46(m, 4H), 1.42-1.28(m, 2H), 0.99-0.92(m, 9H).
실시예 37(13)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-플루오로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.33(헥산:초산에틸=1:1);
NMR(CD3OD): δ 7.60(dd, J=8.7, 5.4Hz, 2H), 7.24(t, J=8.7Hz, 2H), 4.36(s, 2H), 3.99(dd, J=7.5, 4.5Hz, 1H), 3.78(m, 2H), 3.49-3.35(m, 4H), 2.44-2.13(m, 4H), 1.84-1.46(m, 5H), 1.37(m, 2H), 0.99-0.95(m, 9H).
실시예 37(14)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-클로로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.62(헥산:초산에틸=1:1);
NMR(CD3OD): δ 7.72(d, J=7.0Hz, 1H), 7.60(dd, J=8.0, 1.5Hz, 1H), 7.56-7.45(m, 2H), 4.55(s, 2H), 4.00(dd, J=7.5, 4.5Hz, 1H), 3.94(m, 2H), 3.55(m, 2H), 3.42-3.32(m, 2H), 2.43-2.37(m, 2H), 2.26-2. 13(m, 2H), 1.85-1.46(m, 5H), 1.35(m, 2H), 0.97-0.92(m, 9H).
실시예 37(15)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-클로로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.50(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.55(d, J=8.7Hz, 2H), 7.51(d, J=8.7Hz, 2H), 4.34(s, 2H),4.00(dd, J=7.8, 4.5,Hz, 1H), 3.88-3.68(m, 2H), 3.51-3.34(m, 4H), 2.49-2.52(m, 2H), 2.26-2.08(m, 2H), 1.90-1.44(m, 5H), 1. 44-1.29(m, 2H), 1.00-0.89(m, 9H).
실시예 37(16)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3-클로로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.55(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.68-7.64(m, 1H), 7.56-7.45(m, 3H), 4.37(s, 2H), 4.00(dd, J=7.8, 4.5Hz, 1H), 3.91-3.72(m, 2H), 3.54-3.32(m, 4H), 2.53-2.34(m, 2H), 2.27-2.08(m, 2H), 1.90-1.44(m, 5H), 1.44-1.27(m, 2H), 0.99-0.89(m, 9H).
실시예 37(17)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3-메틸-4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.34(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.38-7.30(m, 2H), 6.99(d, J=8.1Hz, 1H), 4.25(s, 2H), 4.00(dd, J=7.8, 4.5Hz, 1H), 3.85(s, 3H), 3.85-3.65(m, 2H), 3.52-3.33(m, 4H), 2.50-2.30(m, 2H), 2.22(s, 3H), 2.20-2.07(m, 2H), 1.90-1.43(m, 5H), 1.43-1.28(m, 2H), 0.99-0.88(m, 9H).
실시예 37(18)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(7-메톡시-1,3-벤조디옥솔란-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.36(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 6.85(d, J=1.8Hz, 1H), 6.74(d, J=1.8Hz, 1H), 5.99(s, 2H),4.25(s, 2H), 4.01(dd, J=7.8, 4.5Hz, 1H), 3.92(s, 3H), 3.87-3.66(m, 2H), 3.52-3.32(m, 4H), 2.52-2.34(m, 2H), 2.26-2.08(m, 2H), 1.90-1.43(m, 5H), 1.43-1.29(m, 2H), 0.99-0.90(m, 9H).
실시예 37(19)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐티오페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.52(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.50-7.36(m, 7H), 7.30(d, J=8.7Hz, 2H), 4.31(s, 2H), 4.00(dd, J=7.8, 4.5Hz, 1H), 3.88-3.68(m, 2H), 3.53-3.32(m, 4H), 2.50-2.30(m, 2H), 2.26-2.06(m, 2H), 1.90-1.42(m, 5H), 1.42-1.27(m, 2H), 0.98-0.89(m, 9H).
실시예 37(20)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-메틸페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.41(클로로포름:메탄올=19:1);
NMR(CD3OD): δ 7.57(d, J=7.8Hz, 1H), 7.42-7.28(m, 3H), 4.41(s, 2H), 4.01(dd, J=7.8, 4.8Hz, 1H), 3.89(m, 2H), 3.53(m, 2H), 3.42(m, 2H), 2.48(s, 3H), 2.48(m, 2H), 2.16(m, 2H), 1.90-1.42(m, 5H), 1.36(sextet, J=7.2Hz, 2H), 0.94(d, J=6.6Hz, 3H), 0.94(t, J=7.2Hz, 3H), 0.93(d, J=6.6Hz, 3H).
실시예 37(21)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3-메틸페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.31(클로로포름:메탄올=19:1);
NMR(CD3OD): δ 7.41-7.29(m, 4H), 4.31(s, 2H), 4.00(dd, J=7.8, 4.8Hz,1H), 3.79(m, 2H), 3.52-3.34(m, 4H), 2.40(m, 2H), 2.40(s, 3H), 2.17(m, 2H), 1.90-1.44(m, 5H), 1.36(sextet, J=7.5Hz, 2H), 0.94(t, J=7.5Hz, 3H), 0.94(d, J=6.6Hz, 3H), 0.93(d, J=6.6Hz, 3H).
실시예 37(22)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-메틸페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.31(클로로포름:메탄올=19:1);
NMR(CD3OD): δ 7.43(d, J=7.8Hz, 2H), 7.31(d, J=7.8Hz, 2H), 4.31(s, 2H), 4.00(dd, J=7.8, 4.8Hz, 1H), 3.78(m, 2H), 3.52-3.35(m, 4H), 2.40(m, 2H), 2.37(s, 3H), 2.17(m, 2H), 1.88-1.44(m, 5H), 1.36(sextet, J=7.5Hz, 2H), 0.94(t, J=7.5Hz, 3H), 0.94(d, J=6.6Hz, 3H), 0.93(d, J=6.6Hz, 3H).
실시예 37(23)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(1-메틸에틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.49(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.48(d, J=8.4Hz, 2H), 7.38(d, J=8.4Hz, 2H), 4.32(s, 2H), 4.01(dd, J=7.8, 4.5Hz, 1H), 3.88-3.70(m, 2H), 3.54-3.36(m, 4H), 3.04-2.88(m, 1H), 2.48-2.30(m, 2H), 2.28-2.08(m, 2H), 1.90-1.28(m, 7H), 1.26(d, J=6.9Hz, 6H), 0.95(t, J=7.2Hz, 3H), 0.95(d, J=6.9Hz, 3H), 0.94(d, J=6.9Hz, 3H).
실시예 37(24)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3-플루오로-4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.44(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.40-7.32(m, 2H), 7.21(m, 1H), 4.31(s, 2H), 4.01(dd,J=7.5, 4.5Hz, 1H), 3.92(s, 3H), 3.86-3.64(m, 2H), 3.58-3.36(m, 4H), 2.56-2.32(m, 2H), 2.28-2.08(m, 2H), 1.90-1.26(m, 7H), 0.96(t, J=7.2Hz, 3H), 0.95(d, J=6.6Hz, 3H), 0.94(d, J=6.6Hz, 3H).
실시예 37(25)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(2-히드록시에틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.22(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.48(d, J=8.7Hz, 2H), 7.07(d, J=8.7Hz, 2H), 4.29(s, 2H), 4.09(t, J=5.1Hz, 2H), 4.01(dd, J=7.5, 4.5Hz, 1H), 3.88(t, J=5.1Hz, 2H), 3.86-3.64(m, 2H), 3.54-3.36(m, 4H), 2.50-2.30(m, 2H), 2.26-2.08(m, 2H), 1.90-1.24(m, 7H), 0.96(t, J=7.2Hz, 3H), 0.95(d, J=6.6Hz, 3H), 0.94(d, J=6.6Hz, 3H).
실시예 37(26)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-히드록시-3-메틸페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.66(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.24(d, J=7.7Hz, 2H), 6.89(t, J=7.7Hz, 1H), 4.36(s, 2H), 4.02(dd, J=7.5, 4.5Hz, 1H), 3.95-3.76(m, 2H), 3.58-3.36(m, 4H), 2.44-2.08(m, 4H), 2.89(s, 3H), 1.90-1.24(m, 7H), 0.96(t, J=7.2Hz, 3H), 0.95(d, J=6.6Hz, 3H), 0.94(d, J=6.6Hz, 3H).
실시예 37(27)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-트리플루오로메틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.49(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.71(d, J=7.8Hz, 2H), 7.42(d, J=7.8Hz, 2H), 4.41(s, 2H),4.01(dd, J=7.8, 4.8Hz, 1H), 3.90-3.72(m, 2H), 3.56-3.36(m, 4H), 2.56-2.36(m, 2H), 2.26-2.08(m, 2H), 1.90-1.28(m, 7H), 0.95(t, J=7.5Hz, 3H), 0.95(d, J=6.3Hz, 3H), 0.94(d, J=6.3Hz, 3H).
실시예 37(28)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3-메틸-5-클로로-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.39(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.59-7.50(m, 5H), 4.35(s, 2H), 4.03(dd, J=7.8, 4.5Hz, 1H), 3.98-3.80(m, 2H), 3.72-3.58(m, 2H), 3.46-3.38(m, 2H), 2.58-2.38(m, 2H), 2.45(s, 3H), 2.36-2.18(m, 2H), 1.92-1.24(m, 7H), 0.97(t, J=7.5Hz, 3H), 0.96(d, J=6.6Hz, 3H), 0.95(d, J=6.6Hz, 3H).
실시예 37(29)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐피리딘-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.28(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 9.17(s, 1H), 8.80(m, 1H), 8.39(m, 1H), 8.03-7.97(m, 2H), 7.73-7.65(m, 3H), 4.65(s, 2H), 4.03(dd, J=7.2, 4.2Hz, 1H), 4.02-3.82(m, 2H), 3.64-3.42(m, 2H), 3.78-3.56(m, 2H), 2.30-2.08(m, 2H), 1.88-1.24(m, 7H), 0.96(d, J=6.3Hz, 3H), 0.95(t, J=7.2Hz, 3H), 0.95(d, J=6.3Hz, 3H).
실시예 37(30)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-메틸설포닐아미노페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.18(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.54(d, J=8.7Hz, 2H), 7.30(d, J=9.0Hz, 2H), 7.08(d,J=8.7Hz, 2H), 7.04(d, J=9.0Hz, 2H), 4.34(s, 2H), 4.02(dd, J=7.8, 4.5Hz, 1H), 3.88-3.68(m, 2H), 3.56-3.35(m, 4H), 2.96(s, 3H), 2.50-2.08(m, 4H), 1.88-1.26(m, 7H), 0.96(t, J=6.9Hz, 3H), 0.95(d, J=6.6Hz, 3H), 0.94(d, J=6.6Hz, 3H).
실시예 37(31)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-메틸설포닐아미노페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.15(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.49(d, J=8.7Hz, 2H), 7.43(d, J=8.7Hz, 2H), 4.33(s, 2H), 4.03(dd, J=7.8, 4.8Hz, 1H), 3.96-3.76(m, 2H), 3.66-3.58(m, 2H), 3.56-3.42(m, 2H), 3.05(s, 3H), 2.68-2.46(m, 2H), 2.44(s, 3H), 2.41(s, 3H), 2.32-2.10(m, 2H), 1.90-1.28(m, 7H), 0.97(t, J=6.6Hz, 3H), 0.96(d, J=6.3Hz, 3H), 0.95(d, J=6.3Hz, 3H).
실시예 37(32)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(5-메틸피리딘-2-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.29(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.12(s, 1H), 7.93(d, J=8.4Hz, 1H), 7.68(d, J=8.7Hz, 2H), 7.30(d, J=8.7Hz, 2H), 7.06(d, J=8.4Hz, 1H), 4.40(s, 2H), 4.03(dd, J=7.8, 4.8Hz, 1H), 3.94-3.76(m, 2H), 3.58-3.40(m, 4H), 2.56-2.36(m, 2H), 2.38(s, 3H), 2.30-2.08(m, 2H), 1.88-1.24(m, 7H), 0.96(t, J=7.8Hz, 3H), 0.96(d, J=6.6Hz, 3H), 0.95(d, J=6.6Hz, 3H).
실시예 37(33)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(6-메틸피리딘-1-옥사이드-3-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.24(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.47(s, 1H), 7.71(d, J=8.7Hz, 2H), 7.62-7.48(m, 2H), 7.29(d, J=8.7Hz, 2H), 4.40(s, 2H), 4.02(dd, J=7.8, 4.5Hz, 1H), 3.92-3.72(m, 2H), 3.58-3.38(m, 4H), 2.64-2.40(m, 2H), 2.60(s, 3H), 2.28-2.10(m, 2H), 1.90-1.28(m, 7H), 0.96(t, J=7.8Hz, 3H), 0.95(d, J=6.6Hz, 3H), 0.94(d, J=6.6Hz, 3H).
실시예 37(34)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(1-(2-메틸프로필옥시카르보닐)인돌-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.23(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.16(d, J=8.4Hz, 1H), 7.82(d, J=1.5Hz, 1H), 7.78(d, J=3.6Hz, 1H), 7.50(dd, J=8.4, 1.5Hz, 1H), 6.75(d, J=3.6Hz, 1H), 4.46(s, 2H), 4.27(d, J=6.6Hz, 2H), 4.01(dd, J=7.8, 4.5Hz, 1H), 3.82-3.74(m, 2H), 3.58-3.36(m, 4H), 2.48-2.30(m, 2H), 2.26-2.08(m, 3H), 1.88-1.24(m, 7H), 1.09(s, 3H), 1.06(s, 3H), 0.95(t, J=7.2Hz, 3H), 0.95(d, J=6.3Hz, 3H), 0.94(d, J=6.3Hz, 3H).
실시예 37(35)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐-5-메틸옥사졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.32(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.05-8.02(m, 2H), 7.52-7.50(m, 3H), 4.35(s, 2H), 4.02(dd, J=7.8, 4.5Hz, 1H), 3.98-3.80(m, 2H), 3.70-3.58(m, 2H), 3.44-3.38(m, 2H), 2.53(s, 3H), 2.53-2.36(m, 2H), 2.34-2.14(m, 2H), 1.90-1.26(m, 7H), 0.96(t, J=7.2Hz, 3H), 0.95(d, J=6.3Hz, 3H), 0.94(d, J=6.3Hz, 3H).
실시예 37(36)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(테트라히드로피란-4-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.33(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.47(d, J=8.4Hz, 2H), 7.07(d, J=8.4Hz, 2H), 4.64(m, 1H), 4.29(s, 2H), 4.01(dd, J=7.5, 4.5Hz, 1H), 3.98-3.91(m, 2H), 3.84-3.68(m, 2H), 3.64-3.56(m, 2H), 3.50-3.37(m, 4H), 2.50-2.30(m, 2H), 2.24-1.98(m, 4H), 1.88-1.26(m, 9H), 0.95(t, J=7.2Hz, 3H), 0.95(d, J=6.3Hz, 3H), 0.94(d, J=6.3Hz, 3H).
실시예 37(37)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(6-메틸피리딘-3-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.22(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.55(d, J=2.7Hz, 1H), 8.10(dd, J=9.0, 2.7Hz, 1H), 7.84(d, J=9.0Hz, 1H), 7.72(d, J=8.7Hz, 2H), 7.29(d, J=8.7Hz, 2H), 4.40(s, 2H), 4.02(dd, J=7.8, 4.5Hz, 1H), 3.94-3.70(m, 2H), 3.58-3.38(m, 4H), 2.74(s, 3H), 2.60-2.42(m, 2H), 2.28-2.08(m, 2H), 1.90-1.26(m, 7H), 0.96(t, J=7.5Hz, 3H), 0.96(d, J=6.6Hz, 3H), 0.95(d, J=6.6Hz, 3H).
실시예 37(38)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-플루오로페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.58(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.55-7.46(m, 2H), 7.36-7.25(m, 2H), 4.30(s, 2H), 4.02(dd, J=7.8, 4.5Hz, 1H), 3.95-3.73(m, 2H), 3.66-3.55(m, 2H), 3.52-3.40(m, 2H), 2.63-2.45(m, 2H), 2.39(s, 3H), 2.37(s, 3H), 2.30-2.10(m, 2H), 1.90-1.43(m, 5H), 1.43-1.30(m, 2H), 0.99-0.91(m, 9H).
실시예 37(39)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(피리딘-2-일)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.52(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.55(d, J=4.8Hz, 1H), 8.12(dd, J=8.4, 7.2Hz, 1H), 7.87(d, J=8.4Hz, 1H), 7.50(dd, J=7.2, 4.8Hz, 1H), 4.32(s, 2H), 4.02(dd, J=7.8, 4.5Hz, 1H), 3.96-3.73(m, 2H), 3.67-3.55(m, 2H), 3.54-3.40(m, 2H), 2.69(s, 3H), 2.70-2.48(m, 2H), 2.44(s, 3H), 2.28-2.08(m, 2H), 1.92-1.43(m, 5H), 1.43-1.26(m, 2H), 0.99-0.90(m, 9H).
실시예 37(40)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-히드록시페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.48(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.30(d, J=9.0Hz, 2H), 6.95(d, J=9.0Hz, 2H),4.33(s, 2H), 4.02(dd, J=7.5, 4.5Hz, 1H), 3.92-3.77(m, 2H), 3.61(m, 2H), 3.47(m, 2H), 2.58(m, 2H), 2.45(s, 3H), 2.36(s, 3H), 2.20(m, 2H), 1.88-1.76(m, 1H), 1.73-1.32(m, 6H), 0.96(t, J=7.5Hz, 3H), 0.95(d, J=6.5Hz, 3H), 0.94(d, J=6.5Hz, 3H).
실시예 37(41)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(2-카르복시에틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.38(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.47(d, J=8.0Hz, 2H), 7.37(d, J=8.0Hz, 2H),4.31(s, 2H), 4.00(dd, J=7.5, 4.5Hz, 1H), 3.86-3.73(m, 2H), 3.49-3.35(m, 4H), 2.96(t, J=7.5Hz, 2H), 2.62(t, J=7.5Hz, 2H), 2.44-2.33(m, 2H), 2.23-2.11(m, 2H), 1.84-1.32(m, 7H), 0.94(t, J=7.5Hz, 3H), 0.94(d, J=6.5Hz, 3H), 0.93(d, J=6.5Hz, 3H).
실시예 37(42)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-(디메틸아미노설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.54(클로로포름:메탄올=9:1);
NMR(CD3OD): δ 7.96(d, J=8.7Hz, 2H), 7.77(d, J=8.7Hz, 2H), 4.32(s, 2H), 4.02(dd, J=7.8, 4.8Hz, 1H), 3.95-3.75(m, 2H), 3.66-3.56(m, 2H), 3.47(m, 2H), 2.74(s, 6H), 2.56(m, 2H), 2.48(s, 3H), 2.41(s, 3H), 2.30-2.12(m, 2H), 1.90-1.46(m, 5H), 1.38(sextet, J=7.2Hz, 2H), 0.98-0.93(m, 9H).
실시예 37(43)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(5-메틸피리딘-1-옥사이드-2-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.41(클로로포름:메탄올=9:1);
NMR(CD3OD): δ 7.77(brs, 1H), 7.65-7.59(m, 2H), 7.56(dd, J=9.3, 2.4Hz, 1H), 7.03-6.97(m, 2H), 6.73(d, J=9.3Hz, 1H), 4.33(s, 2H), 4.00(dd, J=7.8, 4.8Hz, 1H), 3.86-3.68(m, 2H), 3.51-3.36(m, 4H), 2.46(m, 2H), 2.25-2.07(m, 2H), 2.18(s, 3H), 1.90-1.44(m, 5H), 1.36(sextet, J=7.2Hz, 2H), 0.97-0.91(m, 9H).
실시예 37(44)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(2-카르복시-1-에테닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.20(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.75(d, J=8.4Hz, 2H), 7.70(d, J=16.2Hz, 1H), 7.61(d, J=8.4Hz, 2H), 6.58(d, J=16.2Hz, 2H), 4.39(s, 2H), 4.02(dd, J=7.8, 4.5Hz, 1H), 3.92-3.74(m, 2H), 3.58-3.36(m, 4H), 2.50-2.32(m, 2H), 2.30-2.10(m, 2H), 1.90-1.24(m, 7H), 0.96(t, J=7.2Hz, 3H), 0.95(d, J=6.3Hz, 3H), 0.94(d, J=6.3Hz, 3H).
실시예 37(45)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-(2-카르복시-1-에테닐)페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.34(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.69-7.57(m, 5H), 7.14(d, J=8.4Hz, 2H), 7.05(d, J=8.7Hz, 2H), 6.42(d, J=15.9Hz, 1H), 4.36(s, 2H), 4.01(dd, J=7.8, 4.5Hz, 1H), 3.92-3.70(m, 2H), 3.56-3.35(m, 4H), 2.48-2.30(m, 2H), 2.30-2.12(m, 2H), 1.88-1.25(m, 7H), 0.98-0.88(m, 9H).
실시예 37(46)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-아미노카르보닐페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.38(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.90(d, J=8.7Hz, 2H), 7.60(d, J=8.7Hz, 2H), 7.15(d, J=8.7Hz, 2H), 7.07(d, J=8.7Hz, 2H), 4.36(s, 2H), 4.01(dd, J=7.8, 4.5,Hz, 1H), 3.90-3.70(m, 2H), 3.58-3.35(m, 4H), 2.54-2.36(m, 2H), 2.30-2.10(m, 2H), 1.90-1.26(m, 7H), 1.00-0.86(m, 9H).
실시예 37(47)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-아미노설포닐페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.41(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.90(d, J=8.7Hz, 2H), 7.57(d, J=8.7Hz, 2H), 7.17(d, J=8.7Hz, 2H), 7.13(d, J=8.7Hz, 2H), 4.28(brs, 2H), 4.01(dd, J=7.8, 4.5,Hz, 1H), 3.83-3.60(m, 2H), 3.49-3.34(m, 4H), 2.44-2.26(m, 2H), 2.26-2.09(m, 2H), 1.89-1.26(m, 7H), 1.00-0.88(m, 9H).
실시예 37(48)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-벤질피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.40(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.41-7.33(m, 3H), 7.21-7.19(m, 2H), 5.45(s, 2H), 4.30(s, 2H), 4.01(dd, J=7.5, 4.5Hz, 1H), 3.89-3.73(m, 2H), 3.60-3.46(m, 4H), 2.61(m, 2H), 2.48(s, 3H), 2.46(s, 3H), 2.23-2.11(m, 2H), 1.87-1.31(m, 7H), 0.95(t, J=7.0Hz, 3H), 0.94(d, J=6.5Hz, 3H), 0.93(d, J=6.5Hz, 3H).
실시예 37(49)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(2,4-디플루오로페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.40(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.61-7.53(m, 1H), 7.33-7.26(m, 1H), 7.23-7.16(m,1H),4.31(s, 2H), 4.02(dd, J=7.5, 4.5Hz, 1H), 3.92-3.76(m, 2H), 3.63-3.56(m, 2H), 3.49-3.45(m, 2H), 2.57(m, 2H), 2.40(s, 3H), 2.29(s, 3H), 2.19(m, 2H), 1.86-1.34(m, 7H), 0.96(t, J=7.0Hz, 3H), 0.95(d, J=6.5Hz, 3H), 0.94(d, J=6.5Hz, 3H).
실시예 37(50)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(피롤리딘-1-일메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.10(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.75(d, J=8.4Hz, 2H), 7.65(d, J=8.4Hz, 2H), 4.43(s, 2H), 4.40(s, 2H), 4.00(dd, J=7.5, 4.5Hz, 1H), 3.92-3.70(m, 2H), 3.56-3.40(m, 6H), 3.25-3.12(m, 2H), 2.68-2.48(m, 2H), 2.28-1.95(m, 6H), 1.88-1.42(m, 5H), 1.42-1.30(m, 2H), 0.98-0.90(m, 9H).
실시예 37(51)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-(모르폴린-4-일설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.43(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.95(d, J=8.7Hz, 2H), 7.80(d, J=8.7Hz, 2H), 4.32(s, 2H), 4.02(dd, J=7.8, 4.8Hz, 1H), 3.95-3.72(m, 2H), 3.76-3.67(m, 4H), 3.66-3.57(m, 2H), 3.56-3.42(m, 2H), 3.08-2.95(m, 4H), 2.70-2.50(m, 2H), 2.50(s, 3H), 2.42(s, 3H), 2.31-2.10(m, 2H), 1.90-1.44(m, 5H), 1.44-1.30(m, 2H), 1.00-0.91(m, 9H).
실시예 37(52)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-(메틸아미노설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.21(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.01(d, J=8.4Hz, 2H), 7.73(d, J=8.4Hz, 2H), 4.34(s, 2H), 4.04(dd, J=7.8, 4.8Hz, 1H), 3.98-3.78(m, 2H), 3.66-3.58(m, 2H), 3.44-3.30(m, 2H), 2.59(s, 3H), 2.54-2.38(m, 2H), 2.47(s, 3H), 2.40(s, 3H), 2.36-2.16(m, 2H), 1.90-1.26(m, 7H), 0.97(t, J=7.5Hz, 3H), 0.96(d, J=6.6Hz, 6H).
실시예 37(53)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-시아노페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.30(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.75(d, J=8.4Hz, 2H), 7.66(d, J=8.7Hz, 2H), 7.21(d, J=8.4Hz, 2H), 7.14(d, J=8.7Hz, 2H), 4.39(s, 2H), 4.02(dd, J=7.8, 4.5Hz, 1H), 3.94-3.72(m, 2H), 3.58-3.36(m, 4H), 2.58-2.38(m, 2H), 2.28-2.08(m, 2H), 1.88-1.24(m, 7H), 0.96(t, J=7.2Hz, 3H), 0.95(d, J=6.3Hz, 3H), 0.94(d, J=6.3Hz, 3H).
실시예 37(54)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(디메틸아미노메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.16(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.76(d, J=8.1Hz, 2H), 7.63(d, J=8.1Hz, 2H), 4.41(s, 2H), 4.37(s, 2H), 4.00(dd, J=7.8, 4.8Hz, 1H), 3.90-3.72(m, 2H), 3.50-3.42(m, 4H), 2.87(s, 6H), 2.65-2.50(m, 2H), 2.22-2.04(m, 2H), 1.88-1.32(m, 7H), 0.97-0.92(m, 9H).
실시예 37(55)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-(2-디메틸아미노에틸아미노설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·3염산염
TLC: Rf 0.13(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.07(d, J=8.7Hz, 2H), 7.78(d, J=8.7Hz, 2H), 4.31(s, 2H), 4.01(dd, J=8.1, 5.1Hz, 1H), 3.95-3.74(m, 2H), 3.68-3.45(m, 4H), 3.40-3.20(m, 4H), 2.95(s, 6H), 2.70-2.50(m, 2H), 2.49(s, 3H), 2.41(s, 3H), 2.28-2.12(m, 2H), 1.88-1.34(m, 7H), 0.98-0.92(m, 9H).
실시예 37(56)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3-(4-히드록시페닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.53(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.81(s, 1H), 7.69(d, J=7.5Hz, 1H), 7.53(d, J=9.0Hz, 2H), 7.55-7.48(m, 1H), 7.45(d, J=7.5Hz, 1H), 6.87(d, J=9.0Hz, 2H), 4.40(s, 2H), 4.00(dd, J=7.5, 4.5Hz, 1H), 3.94-3.73(m, 2H), 3.56-3.44(m, 2H), 3.44-3.30(m, 2H), 2.53-2.33(m, 2H), 2.26-2.08(m, 2H), 1.90-1.40(m, 5H), 1.43-1.25(m, 2H), 0.94(d, J=6.3Hz, 3H), 0.94(t, J=7.2Hz, 3H), 0.93(d, J=6.3Hz, 3H).
실시예 37(57)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(3-메톡시페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.54(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.53(d, J=8.5Hz, 2H), 7.28(t, J=8.3Hz, 1H), 7.07(d, J=8.5Hz, 2H), 6.75(ddd, J=8.3, 2.3, 1.0Hz, 1H), 6.60-6.57(m, 2H), 4.33(s, 2H), 4.01(dd, J=7.5, 4.5Hz, 1H), 3.86-3.73(m, 2H ), 3.77(s, 3H), 3.51-3.34(m, 4H), 2.41(m, 2H), 2.42-2.12(m, 2H), 1.84-1.33(m, 7H), 0.95(t, J=7.2Hz, 3H), 0.94(d, J=6.5Hz, 3H), 0.93(d, J=6.5Hz, 3H).
실시예 37(58)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(퀴녹살린-2-일)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.52(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 9.51(s, 1H), 8.12(d, J=8.0Hz, 1H),8.04(d, J=8.0Hz, 1H), 7.90-7.80(m, 2H), 4.37(s, 2H), 4.02(dd, J=7.5, 4.5Hz, 1H), 3.96-3.81(m, 2H), 3.63(m, 2H), 3.44(m, 2H), 2.92(s, 3H), 2.47(s, 3H), 2.47(m, 2H), 2.29-2.17(m, 2H), 1.86-1.33(m, 7H), 0.95(t, J=7.2Hz, 3H), 0.95(d, J=6.5Hz, 3H), 0.94(d, J=6.5Hz, 3H).
실시예 37(59)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐카르보닐페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.76(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.88(d, J=8.4Hz, 2H), 7.81-7.67(m, 5H), 7.57-7.52(m, 2H), 4.49(s, 2H), 4.01(dd, J=8.1, 4.8Hz, 1H), 4.00-3.78(m, 2H), 3.59-3.48(m, 2H), 3.44-3.35(m, 2H), 2.50-2.32(m, 2H), 2.32-2.14(m, 2H), 1.88-1.24(m, 7H), 1.02-0.88(m, 9H).
실시예 37(60)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-(N-(2-히드록시에틸)-N-메틸아미노설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.34(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.00(d, J=8.7Hz, 2H), 7.76(d, J=8.7Hz, 2H), 4.34(s, 2H), 4.04(dd, J=7.8, 4.5Hz, 1H), 3.98-3.76(m, 2H), 3.70(t, J=5.7Hz, 2H), 3.68-3.58(m, 2H), 3.50-3.38(m, 2H), 3.20(t, J=5.7Hz, 2H), 2.88(s, 3H), 2.58-2.38(m, 2H), 2.48(s, 3H), 2.41(s, 3H), 2.36-2.16(m, 2H), 1.90-1.24(m, 7H), 0.97(t, J=6.9Hz, 3H), 0.96(d, J=6.3Hz, 3H), 0.95(d, J=6.3Hz, 3H).
실시예 37(61)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(2-페닐에틸)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.24(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.31-7.23(m, 3H), 7.10(d, J=6.6Hz, 2H), 4.44(t, J=6.3Hz, 2H), 4.21(s, 2H), 4.03(dd, J=7.8, 4.8Hz, 1H), 3.82-3.60(m, 2H), 3.58-3.32(m, 4H), 3.13(t, J=6.3Hz, 2H), 2.72-2.52(m, 2H), 2.50(s, 3H), 2.24-2.04(m, 2H), 1.99(s, 3H), 1.90-1.36(m, 7H), 0.97(t, J=7.2Hz, 3H), 0.96(d, J=6.6Hz, 3H), 0.95(d, J=6.6Hz, 3H).
실시예 37(62)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(1,3,5-트리메틸피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.43(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 4.28(s, 2H), 4.00(dd, J=7.8, 4.8Hz, 1H), 3.87(s, 3H), 3.87-3.69(m, 2H), 3.60-3.43(m, 4H), 2.69-2.50(m, 2H), 2.46(s, 3H), 2.44(s, 3H), 2.26-2.08(m, 2H), 1.90-1.28(m, 7H), 0.98-0.85(m, 9H).
실시예 37(63)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(모르폴린-4-일메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.56(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.74(d, J=8.4Hz, 2H), 7.66(d, J=8.4Hz, 2H), 4.40(s, 4H), 4.00(dd, J=7.5, 4.5Hz, 1H), 4.10-3.70(m, 6H), 3.54-3.42(m, 4H), 3.40-3.16(m, 4H), 2.65-2.46(m, 2H), 2.24-2.03(m, 2H), 1.88-1.28(m, 7H), 1.02-0.88(m, 9H).
실시예 37(64)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-메틸피페라진-1-일메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·3염산염
TLC: Rf 0.64(클로로포름:메탄올=5:1);
NMR(CD3OD): δ 7.45(m, 4H), 4.55(s, 2H), 4.42(s, 2H), 4.01(dd, J=7.5, 4.5Hz, 1H), 3.88-3.56(m, 10H), 3.53-3.43(m, 4H), 3.01(s, 3H), 2.59-2.47(m,2H), 2.22-2.09(m, 2H), 1.85-1.33(m, 7H), 0.94(t, J=7.2Hz, 3H), 0.94(d, J=6.5Hz, 3H), 0.93(d, J=6.5Hz, 3H).
실시예 37(65)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐설포닐페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.70(초산에틸:메탄올=9:1);
NMR(CD3OD): δ 8.08(d, J=8.4Hz, 2H), 8.02-7.96(m, 2H), 7.80(d, J=8.4Hz, 2H), 7.70-7.55(m, 3H), 4.43(s, 2H), 3.99(dd, J=7.8, 4.8Hz, 1H), 3.91-3.72(m, 2H), 3.48-3.34(m, 4H), 2.48-2.32(m, 2H), 2.23-2.06(m, 2H), 1.88-1.43(m, 5H), 1.34(sextet, J=7.2Hz, 2H), 0.96-0.90(m, 9H).
실시예 37(66)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-시클로헥실피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.28(초산에틸:메탄올=9:1);
NMR(CD3OD): δ 4.35-4.20(m, 3H), 4.01(dd, J=7.8, 4.8Hz, 1H), 3.90-3.68(m, 2H), 3.58-3.41(m, 4H), 2.60-2.46(m, 2H), 2.45(s, 3H), 2.40(s, 3H), 2.26-2.08(m, 2H), 1.98-1.26(m, 17H), 0.98-0.91(m, 9H).
실시예 37(67)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(3-카르복시페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.11(초산에틸:메탄올=9:1);
NMR(CD3OD): δ 7.83(ddd, J=7.8, 1.5, 0.9Hz, 1H), 7.61(dd, J=2.4, 1.5Hz, 1H), 7.58(d, J=8.7Hz, 2H), 7.51(t, J=7.8Hz, 1H), 7.29(ddd, J=7.8, 2.4, 0.9Hz,1H), 7.11(d, J=8.7Hz, 2H), 4.35(s, 2H), 4.01(dd, J=7.8, 4.8Hz, 1H), 3.90-3.72(m, 2H), 3.57-3.36(m, 4H), 2.50-2.34(m, 2H), 2.28-2.09(m, 2H), 1.89-1.44(m, 5H), 1.36(sextet, J=7.2Hz, 2H), 0.98-0.91(m, 9H).
실시예 37(68)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(피페리딘-1-일메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.52(클로로포름:메탄올=9:1);
NMR(CD3OD): δ 7.75(d, J=8.4Hz, 2H), 7.65(d, J=8.4Hz, 2H), 4.41(s, 2H), 4.34(s, 2H), 4.00(dd, J=7.8, 4.5Hz, 1H), 3.91-3.71(m, 2H), 3.54-3.41(m, 6H), 3.05-2.91(m, 2H), 2.67-2.49(m, 2H), 2.25-2.05(m, 2H), 2.00-1.28(m, 13H), 0.98-0.91(m, 9H).
실시예 37(69)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-(피롤리딘-1-일설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.36(초산에틸:메탄올=9:1);
NMR(CD3OD): δ 8.01(d, J=8.7Hz, 2H), 7.76(d, J=8.7Hz, 2H), 4.32(s, 2H), 4.02(dd, J=7.8, 4.8Hz, 1H), 3.95-3.74(m, 2H), 3.66-3.55(m, 2H), 3.50-3.40(m, 2H), 3.34-3.24(m, 4H), 2.62-2.47(m, 2H), 2.48(s, 3H), 2.40(s, 3H), 2.30-2.11(m, 2H), 1.90-1.45(m, 9H), 1.38(sextet, J=7.2Hz, 2H), 1.00-0.90(m, 9H).
실시예 37(70)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2,3-디히드로벤조푸란-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.56(초산에틸:메탄올=9:1);
NMR(CD3OD): δ 7.40(brs, 1H), 7.26(dd, J=8.1, 1.8Hz, 1H), 6.80(d,J=8.1Hz, 1H), 4.59(t, J=8.7Hz, 2H), 4.26(s, 2H), 4.00(dd, J=7.8, 4.8Hz, 1H), 3.84-3.66(m, 2H), 3.52-3.36(m, 4H), 3.24(t, J=8.7Hz, 2H), 2.49-2.35(m, 2H), 2.25-2.08(m, 2H), 1.89-1.43(m, 5H), 1.36(sextet, J=7.2Hz, 2H), 0.98-0.91(m, 9H).
실시예 37(71)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-(2-히드록시에틸아미노설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.35(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.03(d, J=8.7Hz, 2H), 7.72(d, J=8.7Hz, 2H), 4.32(s, 2H), 4.02(dd, J=7.5, 4.5Hz, 1H), 3.95-3.73(m, 2H), 3.67-3.57(m, 2H), 3.56(t, J=5.7Hz, 2H), 3.51-3.40(m, 2H), 3.01(t, J=5.7Hz, 2H), 2.63-2.42(m, 2H), 2.47(s, 3H), 2.41(s, 3H), 2.32-2.12(m, 2H), 1.92-1.44(m, 5H), 1.44-1.30(m, 2H), 1.00-0.91(m, 9H).
실시예 37(72)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(카르복시메틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.30(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.47(d, J=8.7Hz, 2H), 7.04(d, J=8.7Hz, 2H), 4.71(s, 2H), 4.29(s, 2H), 4.00(dd, J=7.8, 4.5Hz, 1H), 3.88-3.67(m, 2H), 3.53-3.33(m, 4H), 2.46-2.28(m, 2H), 2.26-2.08(m, 2H), 1.90-1.27(m, 7H), 0.99-0.90(m, 9H).
실시예 37(73)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(1-페닐-1-히드록시메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.23(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.62-7.18(m, 9H), 5.82(s, 1H), 4.33(s, 2H), 4.00(dd,J=7.8, 4.8Hz, 1H), 3.88-3.68(m, 2H), 3.56-3.36(m, 4H), 2.48-2.28(m, 2H), 2.24-2.06(m, 2H), 1.88-1.24(m, 7H), 0.95(t, J=6.6Hz, 3H), 0.94(d, J=6.3Hz, 3H), 0.93(d, J=6.3Hz, 3H).
실시예 37(74)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-히드록시피페리딘-1-일메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.16(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.73(d, J=7.8Hz, 2H), 7.69-7.61(m, 2H), 4.42(s, 2H), 4.40-4.34(m, 2H), 4.11-4.05(m, 1H), 4.00(dd, J=7.5, 4.5Hz, 1H), 3.93-3.72(m, 2H), 3.55-3.38(m, 4H), 3.16-3.00(m, 1H), 2.60-2.38(m, 2H), 2.26-2.06(m, 3H), 2.00-1.88(m, 2H), 1.88-1.43(m, 9H), 1.43-1.14(m, 2H), 0.98-0.90(m, 9H).
실시예 37(75)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(3-카르복시페닐메틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.58(클로로포름:메탄올=5:1);
NMR(CD3OD): δ 8.10(s, 1H), 7.98(d, J=8.1Hz, 1H), 7.68(d, J=8.7Hz, 1H), 7.50(t, J=8.1Hz, 1H), 7.47(d, J=8.7Hz, 2H), 7.13(d, J=8.7Hz, 2H), 5.22(s, 2H), 4.29(s, 2H), 4.01(dd, J=7.5, 4.5Hz, 1H), 3.86-3.68(m, 2H), 3.54-3.32(m, 4H), 2.42-2.08(m, 4H), 1.90-1.28(m, 7H), 0.95(t, J=6.9Hz, 3H), 0.95(d, J=6.3Hz, 3H), 0.94(d, J=6.3Hz, 3H).
실시예 37(76)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(비스(메틸설포닐)아미노)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.64(클로로포름:메탄올=5:1);
NMR(CD3OD): δ 7.72(d, J=8.4Hz, 2H), 7.61(d, J=8.4Hz, 2H), 4.44(s, 2H), 4.03(dd, J=7.5, 4.5Hz, 1H), 3.96-3.78(m, 2H), 3.58-3.36(m, 4H), 3.47(s, 6H), 2.50-2.12(m, 4H), 1.92-1.28(m, 7H), 0.96(t, J=6.9Hz, 3H), 0.95(d, J=6.3Hz, 3H), 0.94(d, J=6.3Hz, 3H).
실시예 37(77)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(1,4-벤조디옥산-6-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.34(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.49(d, J=8.7Hz, 2H), 7.02(d, J=8.7Hz, 2H), 6.85(m, 1H), 6.55-6.51(m, 2H), 4.33(s, 2H), 4.24(s, 4H), 4.02(dd, J=7.5, 4.8Hz, 1H), 3.88-3.70(m, 2H), 3.56-3.32(m, 4H), 2.42-2.10(m, 4H), 1.92-1.24(m, 7H), 0.96(t, J=7.2Hz, 3H), 0.95(d, J=6.6Hz, 3H), 0.94(d, J=6.6Hz, 3H).
실시예 37(78)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3-(3-히드록시페닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.19(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.83(s, 1H), 7.74(m, 1H), 7.59-7.51(m, 2H), 7.28(m, 1H), 7.16-7.09(m, 2H), 6.81(m, 1H), 4.44(s, 2H), 4.01(dd, J=7.8, 4.5Hz, 1H), 3.94-3.76(m, 2H), 3.58-3.32(m, 4H), 2.50-2.32(m, 2H), 2.28-2.08(m, 2H), 1.88-1.26(m, 7H), 0.95(t, J=7.2Hz, 3H), 0.95(d, J=6.3Hz, 3H), 0.94(d, J=6.3Hz, 3H).
실시예 37(79)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(메틸설포닐아미노)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.40(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.52(d, J=8.4Hz, 2H), 7.34(d, J=8.4Hz, 2H), 4.32(s, 2H), 4.01(dd, J=7.8, 4.8Hz, 1H), 3.88-3.72(m, 2H), 3.52-3.14(m, 4H), 3.01(s, 3H), 2.46-2.30(m, 2H), 2.28-2.10(m, 2H), 1.88-1.1 0(m, 7H), 0.98-0.90(m, 9H).
실시예 37(80)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(6-(4-메톡시페닐옥시)피리딘-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.48(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.30(m, 1H), 8.05(m, 1H), 7.10-6.86(m, 5H), 4.39(s, 2H), 4.01(dd, J=7.8, 4.8Hz, 1H), 3.90-3.74(m, 2H), 3.81(s, 3H), 3.54-3.32(m, 4H), 2.54-2.32(m, 2H), 2.28-2.05(m, 2H), 1.88-1.26(m, 7H), 0.98-0.90(m, 9H).
실시예 37(81)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-메틸아미노카르보닐페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.54(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.39(brd, J=4.5Hz, 1H), 7.84(d, J=9.0Hz, 2H), 7.59(d, J=9.0Hz, 2H), 7.15(d, J=9.0Hz, 2H), 7.07(d, J=9.0Hz, 2H), 4.35(s, 2H), 4.01(m, 1H), 3.86-3.73(m, 2H), 3.53-3.41(m, 4H), 2.91(d, J=4.5Hz, 3H), 2.55-2.30(m, 2H), 2.30-2.10(m, 2H), 1.90-1.30(m, 7H), 0.95(t, J=6.9Hz, 3H), 0.94(d, J=6.6Hz, 3H), 0.93(d, J=6.6Hz, 3H).
실시예 37(82)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-클로로페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.59(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.53(d, J=8.4Hz, 2H), 7.38(d, J=9.0Hz, 2H), 7.08(d, J=8.4Hz, 2H), 7.02(d, J=9.0Hz, 2H), 4.31(s, 2H), 4.01(m, 1H), 3.90-3.70(m, 2H), 3.60-3.30(m, 4H), 2.50-2.10(m, 4H), 1.90-1. 30(m, 7H), 0.95(t, J=7.2Hz, 3H), 0.94(d, J=6.6Hz, 3H), 0.93(d, J=6.6Hz, 3H).
실시예 37(83)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3-(4-카르복시페닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.60(클로로포름:메탄올=5:1);
NMR(CD3OD): δ 8.13(d, J=9.0Hz, 2H), 7.93(s, 1H), 7.84(m, 1H), 7.81(d, J=9.0Hz, 2H), 7.66-7.56(m, 2H), 4.46(s, 2H), 4.02(dd, J=7.5, 4.8Hz, 1H), 3.96-3.74(m, 2H), 3.58-3.36(m, 4H), 2.48-2.08(m, 4H), 1.88-1.24(m, 7H), 0.95(t, J=6.9Hz, 3H), 0.95(d, J=6.3Hz, 3H), 0.94(d, J=6.3Hz, 3H).
실시예 37(84)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(페닐아미노카르보닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.27(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.07(d, J=8.4Hz, 2H), 7.74(d, J=8.4Hz, 2H), 7.72-7.67(m, 2H), 7.38(t, J=7.5Hz, 2H), 7.17(t, J=7.5Hz, 1H), 4.47(s, 2H), 4.02(dd, J=7.8, 4.5Hz, 1H), 3.96-3.76(m, 2H), 3.58-3.36(m, 4H), 2.54-2.36(m, 2H), 2.28-2.12(m, 2H), 1.90-1.24(m, 7H), 0.96(t, J=7.2Hz, 3H), 0.95(d, J=6.3Hz, 3H), 0.94(d, J=6.3Hz, 3H).
실시예 37(85)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-메틸티오페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.49(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.53(d, J=8.7Hz, 2H), 7.33(d, J=8.7Hz, 2H), 7.07(d, J=8.7Hz, 2H), 7.00(d, J=8.7Hz, 2H), 4.34(s, 2H), 4.02(dd, J=7.8, 4.5Hz, 1H), 3.88-3.68(m, 2H), 3.56-3.36(m, 4H), 2.48(s, 3H), 2.48-2.32(m, 2H), 2.28-2.08(m, 2H), 1.90-1.28(m, 7H), 0.96(t, J=7.2Hz, 3H), 0.95(d, J=6.3Hz, 3H), 0.94(d, J=6.3Hz, 3H).
실시예 37(86)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-(2-디메틸아미노에틸아미노카르보닐)페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.11(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.93(d, J=9.0Hz, 2H), 7.64(d, J=8.7Hz, 2H), 7.15(d, J=8.7Hz, 2H), 7.10(d, J=9.0Hz, 2H), 4.36(s, 2H), 4.01(dd, J=7.8, 4.8Hz, 1H), 3.88-3.70(m, 4H), 3.54-3.36(m, 6H), 2.98(s, 6H), 2.62-2.44(m, 2H), 2.24-2.08(m, 2H), 1.88-1.30(m, 7H), 0.98-0.90(m, 9H).
실시예 37(87)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-아미노카르보닐페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.17(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.98(d, J=8.7Hz, 2H), 7.70(d, J=8.7Hz, 2H), 4.43(s, 2H), 4.00(dd, J=7.5, 4.5Hz, 1H), 3.92-3.74(m, 2H), 3.52-3.36(m, 4H), 2.58-2.40(m, 2H), 2.26-2.08(m, 2H), 1.88-1.28(m, 7H), 0.98-0.88(m, 9H).
실시예 37(88)
(3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-디메틸아미노카르보닐페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.31(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.68(d, J=8.1Hz, 2H), 7.54(d, J=8.1Hz, 2H), 4.41(s, 2H),4.01(dd, J=7.8, 4.8Hz, 1H), 3.92-3.82(m, 2H), 3.54-3.36(m, 4H), 3.11(s, 3H), 2.99(s, 3H), 2.56-2.38(m, 2H), 2.26-2.08(m, 2H), 1.86-1.28(m, 7H), 1.00-0.86(m, 9H).
실시예 38
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-벤질옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸
N-(t-부틸옥시카르보닐)-L-류신 대신에 N-(t-부틸옥시카르보닐)-L-시클로헥실알라닌을 이용하고 실시예 35와 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.35(헥산:초산에틸=1:1);
NMR(CDCl3): δ 7.39-7.31(m, 5H), 6.48(brs, 1H), 5.16(s, 2H), 4.15(brs, 2H), 4.00(ddd, J=9.6, 4.8, 1.5Hz, 1H), 3.76-3.16(m, 4H), 2.02-1.12(m, 19H), 1.08-0.88(m, 2H), 0.92(t, J=7.2Hz, 3H).
실시예 39
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-1,4,9-트리아자스피로[5.5]운데칸·염산염
실시예 38에서 제조한 화합물을 이용하고 실시예 9와 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.08(클로로포름:메탄올:초산=90:10:1);
NMR(CD3OD): δ 4.05(dd, J=7.8, 4.8Hz, 1H), 3.84-3.68(m, 2H), 3.46-3.34(m, 4H), 2.40-2.04(m, 4H), 1.83-1.46(m, 10H), 1.39(sextet, J=7.5Hz, 2H), 1.33-1.15(m, 3H), 1.05-0.86(m, 2H), 0.97(t, J=7.2Hz, 3H).
실시예 40(1)∼40(90)
실시예 39에서 제조한 화합물과 해당하는 알데히드 화합물을 이용하고 실시예 10과 동일한 조작을 하여 이하에 도시한 본 발명 화합물을 얻었다.
실시예 40(1)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-메틸페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.71(초산에틸);
NMR(CD3OD): δ 7.50(d, J=8.7Hz, 2H), 7.19(d, J=8.7Hz, 2H), 7.02(d, J=8.7Hz, 2H), 6.92(d, J=8.7Hz, 2H), 4.32(s, 2H), 4.04(dd, J=7.5, 4.5Hz, 1H), 3.87-3.69(m, 2H), 3.55-3.42(m, 2H), 3.42-3.34(m, 2H), 2.49-2.30(m, 2H), 2.33(s, 3H), 2.30-2.08(m, 2H), 1.82-1.10(m, 15H), 1.05-0.85(m, 2H), 0.95(t, J=7.2Hz, 3H).
실시예 40(2)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-메톡시페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.67(초산에틸);
NMR(CD3OD): δ 7.49(d, J=8.4Hz, 2H), 7.02-6.92(m, 6H), 4.31(s, 2H), 4.03(dd, J=7.5, 4.5Hz, 1H), 3.86-3.69(m, 2H), 3.79(s, 3H), 3.54-3.30(m, 4H), 2.50-2.30(m, 2H), 2.28-2.06(m, 2H), 1.83-1.10(m, 15H), 1.05-0.83(m, 2H), 0.95(t, J=7.2Hz, 3H).
실시예 40(3)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-플루오로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.38(헥산:초산에틸=1:1);
NMR(CD3OD): δ 7.70-7.53(m, 2H), 7.38-7.23(m, 2H), 4.44(s, 2H), 4.03(dd, J=7.5, 4.5Hz, 1H), 3.95-3.77(m, 2H), 3.60-3.45(m, 2H), 3.45-3.30(m, 2H), 2.53-2.34(m, 2H), 2.28-2.08(m, 2H), 1.83-1.10(m, 15H), 1.05-0.82(m, 2H), 0.94(t, J=7.2Hz, 3H).
실시예 40(4)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3-플루오로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.40(헥산:초산에틸=1:1);
NMR(CD3OD): δ 7.57-7.48(m, 1H), 7.44-7.37(m, 2H), 7.30-7.21(m, 1H), 4.38(s, 2H), 4.03(dd, J=7.8, 4.8Hz, 1H), 3.90-3.72(m, 2H), 3.55-3.33(m, 4H), 2.56-2.37(m, 2H), 2.25-2.04(m, 2H), 1.82-1.08(m, 15H), 1.06-0.83(m, 2H), 0.95(t, J=7.2Hz, 3H).
실시예 40(5)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-플루오로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.27(헥산:초산에틸=1:1);
NMR(CD3OD): δ 7.62(dd, J=8.7, 5.1Hz, 2H), 7.23(dd, J=8.7, 8.7Hz, 2H), 4.36(s, 2H), 4.03(dd, J=7.8, 4.8Hz, 1H), 3.88-3.71(m, 2H), 3.53-3.33(m, 4H), 2.53-2.35(m, 2H), 2.27-2.04(m, 2H), 1.82-1.10(m, 15H), 1.05-0.82(m, 2H), 0.94(t, J=7.2Hz, 3H).
실시예 40(6)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3-클로로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.60(헥산:초산에틸=1:1);
NMR(CD3OD): δ 7.65(m, 1H), 7.55-7.49(m, 3H), 4.37(s, 2H), 4.04(dd, J=7.0, 4.5Hz, 1H), 3.83(m, 2H), 3.54-3.47(m, 2H), 3.41-3.35(m, 2H), 2.38(m, 2H), 2.18(m, 2H), 1.78-1.47(m, 9H), 1.42-1.17(m, 6H), 0.95(t, J=7.5Hz, 3H), 0.97-0.92(m, 2H).
실시예 40(7)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-시클로헥실옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.36(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.41(d, J=8.7Hz, 2H), 7.00(d, J=8.7Hz, 2H), 4.36(m, 1H), 4.24(s, 2H), 4.03(dd, J=7.8, 4.5Hz, 1H), 3.82-3.65(m, 2H), 3.50-3.30(m, 4H), 2.42-2.25(m, 2H), 2.25-2.06(m, 2H), 2.02-1.92(m, 2H), 1.84-1.14(m, 23H), 1.04-0.89(m, 5H).
실시예 40(8)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-메톡시-3-히드록시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.34(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.01(d, J=7.8Hz, 1H), 6.99-6.93(m, 2H), 4.22(s, 2H), 4.03(dd, J=7.5, 4.8Hz, 1H), 3.87(s, 3H), 3.83-3.67(m, 2H), 3.52-3.42(m, 2H), 3.42-3.33(m, 2H), 2.44-2.27(m, 2H), 2.26-2.07(m, 2H), 1.83-1.12(m, 15H), 1.04-0.89(m, 5H).
실시예 40(9)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-클로로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.77(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.69(dd, J=7.5, 2.1Hz, 1H), 7.60(dd, J=7.5, 2.1Hz, 1H), 7.51(dt, J=2.1, 7.5Hz, 1H), 7.47(dt, J=2.1, 7.5Hz, 1H), 4.52(s, 2H), 4.04(dd, J=7.8, 4.8Hz, 1H), 4.00-3.82(m, 2H), 3.60-3.48(m, 2H), 3.43-3.34(m, 2H), 2.48-2.29(m, 2H), 2.28-2.07(m, 2H), 1.83-1.44(m, 10H), 1.43-1.12(m, 5H), 1.04-0.88(m, 5H).
실시예 40(10)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-메틸페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.77(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.56(d, J=7.2Hz, 1H), 7.41-7.30(m, 3H), 4.41(s, 2H), 4.04(dd, J=7.5, 4.5Hz, 1H), 3.98-3.79(m, 2H), 3.57-3.48(m, 2H), 3.44-3.39(m, 2H), 2.56-2.38(m, 2H), 2.48(s, 3H), 2.26-2.06(m, 2H), 1.82-1.15(m, 15H), 1.02-0.84(m, 5H).
실시예 40(11)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3-메틸페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.58(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.40-7.28(m, 4H), 4.31(s, 2H), 4.03(dd, J=7.5, 4.5Hz,1H), 3.84-3.70(m, 2H), 3.52-3.46(m, 4H), 2.51-2.30(m, 2H), 2.39(s, 3H), 2.24-2.04(m, 2H), 1.80-1.12(m, 15H), 1.02-0.84(m, 5H).
실시예 40(12)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-메틸페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.61(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.44(d, J=8.4Hz, 2H), 7.31(d, J=8.4Hz, 2H), 4.31(s, 2H), 4.03(dd, J=7.5, 4.5Hz, 1H), 3.88-3.70(m, 2H), 3.52-3.36(m, 4H), 2.48-2.30(m, 2H), 2.38(s, 3H), 2.30-2.08(m, 2H), 1.81-1.1 0(m, 15H), 1.04-0.82(m, 5H).
실시예 40(13)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-페닐티오페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.74(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.50-7.37(m, 7H), 7.29(d, J=8.4Hz, 2H), 4.31(s, 2H), 4.03(dd, J=7.5, 4.8Hz, 1H), 3.84-3.70(m, 2H), 3.50-3.32(m, 4H), 2.56-2.38(m, 2H), 2.24-2.05(m, 2H), 1.81-1.06(m, 15H), 1.02-0.84(m, 5H).
실시예 40(14)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3-(2-메틸프로필)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.41(클로로포름:메탄올=19:1);
NMR(CD3OD): δ 7.47(d, J=7.5Hz, 2H), 7.29(d, J=7.5Hz, 2H), 4.32(s, 2H),4.03(dd, J=7.8, 4.8Hz, 1H), 3.80(m, 2H), 3.56-3.36(m, 4H), 2.52(d, J=7.2Hz, 2H), 2.45(m, 2H), 2.16(m, 2H), 1.96-1.14(m, 16H), 0.97-0.89(m, 11H).
실시예 40(15)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3-부틸페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.37(클로로포름:메탄올=19:1);
NMR(CD3OD): δ 7.46(d, J=8.4Hz, 2H), 7.32(d, J=8.4Hz, 2H), 4.31(s, 2H), 4.03(dd, J=7.2, 4.8Hz, 1H), 3.79(m, 2H), 3.56-3.36(m, 4H), 2.66(t, J=7.5Hz, 2H), 2.41(m, 2H), 2.16(m, 2H), 1.82-1.20(m, 19H), 1.00-0.89(m, 2H), 0.94(t, J=7.2Hz, 3H), 0.93(t, J=7.2Hz, 3H).
실시예 40(16)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-이소프로필페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.63(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.46(d, J=8.4Hz, 2H), 7.37(d, J=8.4Hz, 2H), 4.32(s, 2H), 4.03(dd, J=7.8, 4.8Hz, 1H), 3.88-3.74(m, 2H), 3.52-3.43(m, 2H), 3.43-3.32(m, 2H), 3.02-2.90(m, 1H), 2.45-2.25(m, 2H), 2.2 5-2.08(m, 2H), 1.80-1.12(m, 21H), 1.04-0.88(m, 5H).
실시예 40(17)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-메톡시-3-플루오로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.58(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.40-7.31(m, 2H), 7.22-7.17(m, 1H), 4.30(s, 2H), 4.03(dd, J=7.8, 4.8Hz, 1H), 3.90(s, 3H), 3.86-3.70(m, 2H), 3.50-3.38(m, 4H), 2.52-2.32(m, 2H), 2.26-2.05(m, 2H), 1.80-1.15(m, 15H), 1.01-0.88(m, 5H).
실시예 40(18)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(2-히드록시에톡시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.40(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.47(d, J=8.7Hz, 2H), 7.06(d, J=8.7Hz, 2H), 4.29(s, 2H), 4.08-4.00(m, 3H), 3.89-3.84(m, 2H), 3.84-3.68(m, 2H), 3.52-3.36(m, 4H), 2.48-2.30(m, 2H), 2.25-2.08(m, 2H), 1.80-1.10(m, 15H), 1.04-0.86(m, 5H).
실시예 40(19)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-히드록시-3-메틸페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.85(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.30-7.21(m, 2H), 6.88(t, J=7.5Hz, 1H), 4.36(s, 2H), 4.03(dd, J=7.8, 4.2Hz, 1H), 3.94-3.78(m, 2H), 3.56-3.46(m, 2H), 3.42-3.32(m, 2H), 2.50-2.30(m, 2H), 2.28(s, 3H), 2.28-2.06(m, 2H), 1.82-1.01(m, 15H), 1.00-0.87(m, 5H).
실시예 40(20)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-클로로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.60(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.57(d, J=8.7Hz, 2H), 7.51(d, J=8.7Hz, 2H), 4.36(s, 2H), 4.03(dd, J=7.5, 4.8Hz, 1H), 3.89-3.71(m, 2H), 3.53-3.33(m, 4H), 2.52-2.32(m, 2H), 2.26-2.07(m, 2H), 1.83-1.06(m, 15H), 1.04-0.84(m, 2H), 0.95(t, J=6.9Hz, 3H).
실시예 40(21)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(7-메톡시-1,3-벤조디옥솔란-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.43(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 6.85(s, 1H), 6.74(s, 1H), 5.99(s, 2H), 4.25(s, 2H), 4.03(dd, J=7.5, 4.5Hz, 1H), 3.92(s, 3H), 3.87-3.67(m, 2H), 3.54-3.34(m, 4H), 2.53-2.30(m, 2H), 2.25-2.05(m, 2H), 1.83-1.10(m, 15H), 1.06-0.83(m, 2H), 0.95(t, J=7.2Hz, 3H).
실시예 40(22)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3-메틸-4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.38(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.37-7.28(m, 2H), 6.99(d, J=8.1Hz, 1H), 4.25(s, 2H), 4.03(dd, J=7.5, 4.5Hz, 1H), 3.85(s, 3H), 3.84-3.66(m, 2H), 3.52-3.32(m, 4H), 2.48-2.28(m, 2H), 2.22(s, 3H), 2.22-2.05(m, 2H), 1.83-1.10(m, 15H), 1.06-0.83(m, 2H), 0.94(t, J=6.9Hz, 3H).
실시예 40(23)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-플루오로페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.53(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.53(d, J=8.7Hz, 2H), 7.18-7.00(m, 6H), 4.33(s, 2H), 4.04(dd, J=7.5, 4.5Hz, 1H), 3.87-3.69(m, 2H), 3.55-3.32(m, 4H), 2.52-2.32(m, 2H), 2.28-2.08(m, 2H), 1.83-1.12(m, 15H), 1.06-0.83(m, 2H), 0.95(t, J=7.2Hz, 3H).
실시예 40(24)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-트리플루오로메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.60(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.72-7.69(m, 2H), 7.41(d, J=7.8Hz, 2H), 4.40(s, 2H), 4.03(dd, J=7.5, 4.5Hz, 1H), 3.90-3.75(m, 2H), 3.52-3.38(m, 4H), 2.54-2.32(m, 2H), 2.28-2.10(m, 2H), 1.80-1.10(m, 15H), 1.02-0.88(m, 5H).
실시예 40(25)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3-메틸-5-클로로-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.50(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.56-7.50(m, 5H), 4.33(s, 2H), 4.05(dd, J=7.8, 4.5Hz, 1H), 3.98-3.80(m, 2H), 3.70-3.59(m, 2H), 3.50-3.40(m, 2H), 2.60-2.38(m, 2H), 2.45(s, 3H), 2.32-2.14(m, 2H), 1.82-1.14(m, 15H), 1. 02-0.86(m, 5H).
실시예 40(26)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2,3-디메틸-5-옥소-1-페닐피라졸린-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.27(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.62-7.48(m, 3H), 7.44-7.38(m, 2H), 4.13(s, 2H),4.04(dd, J=7.5, 4.5Hz, 1H), 3.88-3.72(m, 2H), 3.64-3.52(m, 2H), 3.50-3.38(m, 2H), 3.35(s, 3H), 2.60-2.40(m, 2H), 2.48(s, 3H), 2.28-2.1 0(m, 2H), 1.82-1.10(m, 15H), 1.02-0.84(m, 5H).
실시예 40(27)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(1-(2-메틸프로필옥시카르보닐)인돌-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.55(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.26(d, J=8.4Hz, 1H), 7.82(s, 1H), 7.76(d, J=3.6Hz, 1H), 7.50(dd, J=8.4, 1.8Hz, 1H), 6.74(d, J=3.6Hz, 1H), 4.44(s, 2H), 4.25(d, J=6.6Hz, 2H), 4.03(dd, J=7.8, 4.8Hz, 1H), 3.86-3.72(m, 2H), 3.52-3.40(m, 4H), 2.52-2.36(m, 2H), 2.25-2.06(m, 3H), 1.80-1.10(m, 15H), 1.07(d, J=9.0Hz, 6H), 1.00-0.84(m, 5H).
실시예 40(28)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-메틸-2-페닐옥사졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.48(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.04-8.00(m, 2H), 7.51-7.49(m, 3H), 4.34(s, 2H), 4.04(dd, J=7.8, 4.8Hz, 1H), 3.98-3.82(m, 2H), 3.70-3.60(m, 2H), 3.44-3.38(m, 2H), 2.52(s, 3H), 2.50-2.36(m, 2H), 2.28-2.12(m, 2H), 1.80-1.12(m, 15H), 1.00-0.86(m, 5H).
실시예 40(29)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-메틸설포닐아미노페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.32(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.47(d, J=9.0Hz, 2H), 7.41(d, J=9.0Hz, 2H), 4.32(s, 2H), 4.04(dd, J=7.8, 4.8Hz, 1H), 3.92-3.76(m, 2H), 3.65-3.58(m, 2H), 3.52-3.45(m, 2H), 3.04(s, 3H), 2.64-2.50(m, 2H), 2.43(s, 3H), 2.40(s, 3H), 2.28-2.12(m, 2H), 1.82-1.10(m, 15H), 1.00-0.88(m, 5H).
실시예 40(30)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-메틸설포닐아미노페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.42(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.53(d, J=9.0Hz, 2H), 7.29(d, J=9.0Hz, 2H), 7.08-7.00(m, 4H), 4.33(s, 2H), 4.03(dd, J=7.5, 4.8Hz, 1H), 3.85-3.72(m, 2H), 3.54-3.36(m, 4H), 2.95(s, 3H), 2.48-2.34(m, 2H), 2.25-2.08(m, 2H), 1.80-1.14(m, 15H), 0.98-0.88(m, 5H).
실시예 40(31)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(6-메틸피리딘-3-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.42(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.58(d, J=2.7Hz, 1H), 8.17(m, 1H), 7.90(d, J=8.4Hz, 1H), 7.75(d, J=9.0Hz, 2H), 7.30(d, J=9.0Hz, 2H), 4.39(s, 2H), 4.03(dd, J=7.5, 4.8Hz, 1H), 3.88-3.72(m, 2H), 3.56-3.44(m, 4H), 2.76(s, 3H), 2.68-2.50(m, 2H), 2.24-2.06(m, 2H), 1.82-1.14(m, 15H), 1.02-0.88(m, 5H).
실시예 40(32)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(6-메틸피리딘-1-옥사이드-3-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.38(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.40(m, 1H), 7.69(d, J=8.4Hz, 2H), 7.69(m, 1H), 7.54(m, 1H), 7.27(d, J=8.4Hz, 2H), 4.39(s, 2H), 4.04(dd, J=7.5, 4.8Hz, 1H), 3.88-3.72(m, 2H), 3.58-3.39(m, 4H), 2.59(s, 3H), 2.58-2.40(m, 2H), 2.28-2.06(m, 2H), 1.82-1.10(m, 15H), 1.02-0.84(m, 5H).
실시예 40(33)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(테트라히드로피란-4-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.48(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.49(d, J=8.4Hz, 2H), 7.05(d, J=8.4Hz, 2H), 4.63(m, 1H), 4.27(s, 2H), 4.02(dd, J=7.8, 4.8Hz, 1H), 3.97-3.90(m, 2H), 3.84-3.66(m, 2H), 3.62-3.52(m, 2H), 3.50-3.38(m, 3H), 2.5 4-2.38(m, 2H), 2.22-1.98(m, 4H), 1.80-1.10(m, 18H), 1.00-0.86(m, 5H).
실시예 40(34)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(6-페닐피리딘-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.50(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 9.14(m, 1H), 8.75(m, 1H), 8.36(m, 1H), 8.02-7.99(m, 2H), 7.68-7.62(m, 3H), 4.63(s, 2H), 4.05(dd, J=7.5, 4.5Hz, 1H), 4.02-3.94(m, 2H), 3.64-3.42(m, 4H), 2.72-2.56(m, 2H), 2.25-2.06(m, 2H), 1.80-1.10(m, 15H), 1.00-0.86(m, 5H).
실시예 40(35)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-플루오로페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.60(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.58-7.50(m, 2H), 7.37-7.28(m, 2H), 4.32(s, 2H), 4.05(dd, J=7.5, 4.5Hz, 1H), 3.94-3.73(m, 2H), 3.67-3.55(m, 2H), 3.53-3.42(m, 2H), 2.70-2.48(m, 2H), 2.43(s, 3H), 2.39(s, 3H), 2.30-2.08(m, 2H), 1.84-1.10(m, 15H), 1.08-0.93(m, 2H), 0.95(t, J=7.2Hz, 3H).
실시예 40(36)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(피리딘-2-일)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.60(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.53(dd, J=4.8, 1.5Hz, 1H), 8.11-8.00(m, 1H), 7.84(d, J=8.4Hz, 1H), 7.49-7.41(m, 1H), 4.32(s, 2H), 4.05(dd, J=7.5, 4.5Hz, 1H), 3.95-3.74(m, 2H), 3.66-3.54(m, 2H), 3.50-3.37(m, 2H), 2.68(s, 3H), 2.64-2.40(m, 2H), 2.43(s, 3H), 2.30-2.08(m, 2H), 1.93-1.10(m, 15H), 1.08-0.92(m, 2H), 0.95(t, J=7.2Hz, 3H).
실시예 40(37)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-히드록시페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.48(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.34(d, J=9.0Hz, 2H), 6.96(d, J=9.0Hz, 2H),4.35(s, 2H), 4.05(dd, J=7.5, 4.5Hz, 1H), 3.93-3.78(m, 2H), 3.64-3.61(m, 2H), 3.50(t, J=8.0Hz, 2H), 2.68-2.56(m, 2H), 2.49(s, 3H), 2.3 9(s, 3H), 2.25-2.12(m, 2H), 1.81-1.19(m, 15H), 0.95(t, J=7.5Hz, 3H), 0.99-0.91(m, 2H).
실시예 40(38)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(2-카르복시에틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.43(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.46(d, J=8.3Hz, 2H), 7.38(d, J=8.3Hz, 2H),4.32(s, 2H), 4.03(dd, J=7.5, 4.5Hz, 1H), 3.85-3.74(m, 2H), 3.50-3.46(m, 2H), 3.40-3.35(m, 2H), 2.96(t, J=7.2Hz, 2H), 2.62(t, J=7.2Hz, 2H), 2.42-2.30(m, 2H), 2.34-2.10(m, 2H), 1.78-1.18(m, 15H), 0.94(t, J=7.2Hz, 3H), 0.94(m, 2H).
실시예 40(39)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-히드록시페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.54(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.47(d, J=8.4Hz, 2H), 6.97(d, J=8.4Hz, 2H), 6.88(d, J=9.0Hz, 2H), 6.80(d, J=9.0Hz, 2H), 4.30(s, 2H), 4.03(dd, J=7.5, 4.5Hz, 1H), 3.83-3.72(m, 2H), 3.49-3.34(m, 4H), 2.38(m, 2H), 2.23-2.10(m, 2H), 1.78-1.16(m, 15H), 1.02-0.92(m, 2H), 0.95(t, J=7.2Hz, 3H).
실시예 40(40)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-카르복시페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.25(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.19(d, J=8.4Hz, 2H), 7.61(d, J=8.4Hz, 2H), 4.33(s, 2H), 4.06(dd, J=7.5, 4.5Hz, 1H), 3.93-3.80(m, 2H), 3.61(m, 2H), 3.43-3.38(m, 2H), 2.44(s, 3H), 2.40(m, 2H), 2.39(s, 3H), 2.21(m, 2H), 1.75-1.18(m, 15H), 0.96(m, 2H), 0.96(t, J=7.2Hz, 3H).
실시예 40(41)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-(디메틸아미노설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.54(클로로포름:메탄올=9:1);
NMR(CD3OD): δ 7.96(d, J=8.7Hz, 2H), 7.78(d, J=8.7Hz, 2H), 4.31(s, 2H), 4.05(dd, J=7.8, 4.5Hz, 1H), 3.94-3.74(m, 2H), 3.66-3.56(m, 2H), 3.48(m, 2H), 2.74(s, 6H), 2.59(m, 2H), 2.49(s, 3H), 2.41(s, 3H), 2.29-2.10(m, 2H), 1.84-1.16(m, 13H), 1.06-0.86(m, 5H).
실시예 40(42)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(5-메틸피리딘-1-옥사이드-2-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.49(클로로포름:메탄올=9:1);
NMR(CD3OD): δ 7.77(brs, 1H), 7.61(d, J=7.5Hz, 2H), 7.56(dd, J=9.3, 2.4Hz, 1H), 7.00(d, J=7.5Hz, 2H), 6.73(d, J=9.3Hz, 1H), 4.34(s, 2H), 4.03(dd, J=7.8, 4.8Hz, 1H), 3.86-3.69(m, 2H), 3.52-3.35(m, 4H), 2.44(m, 2H), 2.25-2.06(m, 2H), 2.18(s, 3H), 1.84-1.14(m, 15H), 1.04-0.96(m, 5H).
실시예 40(43)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(2-카르복시-1-에티닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.17(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.75(d, J=8.4Hz, 2H), 7.70(d, J=15.9Hz, 1H), 7.61(d, J=8.4Hz, 2H), 6.57(d, J=15.9Hz, 1H), 4.39(s, 2H),4.04(dd, J=7.2, 4.8Hz, 1H), 3.90-3.72(m, 2H), 3.58-3.36(m, 4H), 2.50-2.32(m, 2H), 2.28-2.08(m, 2H), 1.92-1.10(m, 15H), 0.96(t, J=7.2Hz, 3H), 0.96(m, 2H).
실시예 40(44)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-((1E)-2-카르복시-1-에티닐)페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.44(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.69-7.63(m, 3H), 7.57(d, J=8.7Hz, 2H), 7.14(d, J=8.7Hz, 2H), 7.05(d, J=8.4Hz, 2H), 6.42(d, J=15.9Hz, 1H), 4.36(s, 2H), 4.03(dd, J=7.5, 4.5Hz, 1H), 3.90-3.74(m, 2H), 3.55-3.36(m, 4H), 2.50-2.30(m, 2H), 2.30-2.08(m, 2H), 1.82-1.10(m, 15H), 1.02-0.88(m, 5H).
실시예 40(45)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-아미노카르보닐페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.41(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.90(d, J=9.0Hz, 2H), 7.60(d, J=9.0Hz, 2H), 7.15(d, J=9.0Hz, 2H), 7.07(d, J=9.0Hz, 2H), 4.36(s, 2H), 4.04(dd, J=7.5, 4.5,Hz, 1H), 3.90-3.72(m, 2H), 3.56-3.35(m, 4H), 2.53-2.35(m, 2H), 2.28-2.08(m, 2H), 1.84-1.13(m, 15H), 1.06-0.86(m, 5H).
실시예 40(46)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-아미노설포닐페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.33(클로로포름:메탄올=10:1);
NMR(d6-DMSO):δ 11.03(brs, 1H), 8.42(brs, 1H), 7.82(d, J=8.7Hz, 2H), 7.71(d, J=8.7Hz, 2H), 7.33(brs, 2H), 7.16(d, J=8.7Hz, 4H), 4.38-4.23(m, 2H), 3.91(m, 1H), 3.61-3.23(m, 6H), 2.58-2.30(m, 2H), 2.18-1.91(m, 2H), 1.76-1.00(m, 15H), 0.98-0.71(m, 5H).
실시예 40(47)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-벤질피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.40(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.41-7.33(m, 3H), 7.22-7.20(m, 2H), 5.46(s, 2H), 4.31(s, 2H), 4.04(dd, J=7.5, 4.5Hz, 1H), 3.88-3.74(m, 2H), 3.58-3.48(m, 4H), 2.61(m, 2H), 2.47(s, 6H), 2.24-2.09(m, 2H), 1.80-1.16(m, 15H), 0.95(t, J=7.2Hz, 3H), 0.95(m, 2H).
실시예 40(48)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(2,4-디플루오로페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.48(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.58-7.51(m, 1H), 7.33-7.25(m, 1H), 7.22-7.16(m, 1H),4.31(s, 2H), 4.05(dd, J=7.5, 4.5Hz, 1H), 3.91-3.78(m, 2H), 3.59(m, 2H), 3.44(m, 2H), 2.49(m, 2H), 2.38(s, 3H), 2.28(s, 3H), 2.27-2.15(m, 2H), 1.81-1.16(m, 15H), 0.96(t, J=7.0Hz, 3H), 0.96(m, 2H).
실시예 40(49)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(피롤리딘-1-일메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.14(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.74(d, J=8.4Hz, 2H), 7.65(d, J=8.4Hz, 2H), 4.43(s, 2H), 4.40(s, 2H), 4.03(dd, J=7.5, 4.5Hz, 1H), 3.90-3.70(m, 2H), 3.56-3.38(m, 6H), 3.28-3.10(m, 2H), 2.66-2.48(m, 2H), 2.26-1.92(m, 6H), 1.83-1.10(m, 15H), 1.06-0.83(m, 2H), 0.94(t, J=7.2Hz, 3H).
실시예 40(50)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-(모르폰-4-일설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.46(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.95(d, J=8.7Hz, 2H), 7.80(d, J=8.7Hz, 2H), 4.32(s, 2H),4.05(dd, J=7.8, 4.5Hz, 1H), 3.94-3.74(m, 2H), 3.76-3.67(m, 4H), 3.66-3.56(m, 2H), 3.56-3.42(m, 2H), 3.10-2.92(m, 4H), 2.68-2.50(m, 2H), 2.50(s, 3H), 2.42(s, 3H), 2.30-2.08(m, 2H), 1.84-1.08(m, 15H), 1.08-0.83(m, 2H), 0.95(t, J=7.2Hz, 3H).
실시예 40(51)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-시아노페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.33(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.75(d, J=9.3Hz, 2H), 7.64(d, J=9.0Hz, 2H), 7.22(d, J=9.0Hz, 2H), 7.14(d, J=9.3Hz, 2H), 4.40(s, 2H), 4.05(dd, J=7.5, 4.8Hz, 1H), 3.92-3.74(m, 2H), 3.58-3.36(m, 4H), 2.52-2.36(m, 2H), 2.32-2.08(m, 2H), 1.84-1.12(m, 15H), 0.96(t, J=7.2Hz, 3H), 0.96(m, 2H).
실시예 40(52)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-(N-(2-히드록시에틸)-N-메틸아미노설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.68(클로로포름:메탄올=5:1);
NMR(CD3OD): δ 8.00(d, J=8.7Hz, 2H), 7.78(d, J=8.7Hz, 2H), 4.33(s, 2H), 4.06(dd, J=7.5, 4.5Hz, 1H), 3.86-3.76(m, 2H), 3.70(t, J=5.7Hz, 2H), 3.68-3.60(m, 2H), 3.58-3.42(m, 2H), 3.20(t, J=5.7Hz, 2H), 2.88(s, 3H), 2.72-2.58(m, 2H), 2.50(s, 3H), 2.44(s, 3H), 2.28-2.06(m, 2H), 1.82-1.10(m, 15H), 0.96(t, J=7.2Hz, 3H), 0.96(m, 2H).
실시예 40(53)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(2-페닐에틸)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.24(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.28-7.23(m, 3H), 7.10-7.07(m, 2H), 4.40(t, J=6.6Hz, 2H), 4.19(s, 2H), 4.06(dd, J=7.2, 4.8Hz, 1H), 3.80-3.60(m, 2H), 3.58-3.36(m, 4H), 3.12(t, J=6.6Hz, 2H), 2.64-2.45(m, 2H), 2.45(s, 3H), 2.26-2.04(m, 2H), 1.95(s, 3H), 1.84-1.14(m, 15H), 0.97(t, J=7.5Hz, 3H), 0.97(m, 2H).
실시예 40(54)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(디메틸아미노메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.16(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.76(d, J=8.1Hz, 2H), 7.63(d, J=8.1Hz, 2H), 4.41(s, 2H), 4.37(s, 2H), 4.03(dd, J=7.8, 5.1Hz, 1H), 3.90-3.75(m, 2H), 3.52-3.38(m, 4H), 2.87(s, 6H), 2.64-2.48(m, 2H), 2.22-2.04(m, 2H), 1.80-1.15(m, 15H), 1.00-0.86(m, 5H).
실시예 40(55)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3-(4-히드록시페닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.58(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.81(s, 1H), 7.69(d, J=7.5Hz, 1H), 7.54(d, J=9.0Hz, 2H), 7.55-7.48(m, 1H), 7.45(d, J=7.5Hz, 1H), 6.87(d, J=9.0Hz, 2H), 4.40(s, 2H), 4.03(dd, J=7.5, 4.5Hz, 1H), 3.92-3.73(m, 2H), 3.58-3.43(m, 2H), 3.43-3.32(m, 2H), 2.55-2.35(m, 2H), 2.28-2.06(m, 2H), 1.82-1.10(m, 15H), 1.08-0.83(m, 2H), 0.94(t, J=7.2Hz, 3H).
실시예 40(56)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(퀴녹살린-2-일)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.67(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 9.51(s, 1H), 8.13(d, J=8.0Hz, 1H),8.05(d, J=8.0Hz, 1H), 7.91-7.80(m, 2H), 4.38(s, 2H), 4.05(dd, J=7.5, 4.5Hz, 1H), 3.96-3.82(m, 2H), 3.63(m, 2H), 3.42(m, 2H), 2.92(s, 3H), 2.47(s, 3H), 2.47(m, 2H), 2.29-2.16(m, 2H), 1.80-1.18(m, 15H), 0.95(t, J=7.2Hz, 3H), 0.95(m, 2H).
실시예 40(57)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(페닐카르보닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.68(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.87(d, J=8.4Hz, 2H), 7.82-7.74(m, 4H), 7.67(t, J=8.4Hz, 1H), 7.57-7.51(m, 2H), 4.48(s, 2H), 4.04(dd, J=7.8, 4.8Hz, 1H), 3.84-3.78(m, 2H), 3.58-3.38(m, 4H), 2.58-2.40(m, 2H), 2.30-2.10(m, 2H), 1.82-1.14(m, 15H), 1.02-0.86(m, 5H).
실시예 40(58)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-메틸아미노설포닐페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.30(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.01(d, J=8.7Hz, 2H), 7.74(d, J=8.7Hz, 2H), 4.33(s, 2H), 4.06(dd, J=7.8, 4.5Hz, 1H), 3.86-3.78(m, 2H), 3.68-3.58(m, 2H), 3.52-3.36(m, 2H), 2.59(s, 3H), 2.59-2.38(m, 2H), 2.48(s, 3H), 2.41(s, 3H), 2.34-2.10(m, 2H), 1.84-1.16(m, 15H), 0.97(t, J=7.2Hz, 3H), 0.97(m, 2H).
실시예 40(59)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(1,3,5-트리메틸피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.43(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 4.28(s, 2H), 4.03(dd, J=7.8, 4.5Hz, 1H), 3.87(s, 3H), 3.87-3.69(m, 2H), 3.61-3.43(m, 4H), 2.69-2.50(m, 2H), 2.46(s, 3H), 2.44(s, 3H), 2.25-2.06(m, 2H), 1.83-1.12(m, 15H), 1.05-0.86(m, 5H).
실시예 40(60)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(모르폴린-4-일메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.56(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.74(d, J=8.4Hz, 2H), 7.66(d, J=8.4Hz, 2H), 4.40(s, 4H), 4.03(dd, J=7.5, 4.5Hz, 1H), 4.00-3.70(m, 6H), 3.54-3.40(m, 4H), 3.35-3.18(m, 4H), 2.63-2.47(m, 2H), 2.24-2.02(m, 2H), 1.83-1.12(m, 15H), 1.06-0.85(m, 5H).
실시예 40(61)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(3-메톡시페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.57(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.53(d, J=8.7Hz, 2H), 7.28(t, J=8.4Hz, 1H), 7.07(d, J=8.7Hz, 2H), 6.75(ddd, J=8.4, 2.4, 1.0Hz, 1H), 6.61-6.57(m, 2H), 4.34(s, 2H), 4.04(dd, J=7.5, 4.5Hz, 1H), 3.85-3.55(m, 2H ), 3.77(s, 3H), 3.53-3.47(m, 2H), 3.40(m, 2H), 2.50-2.35(m, 2H), 2.25-2.11(m, 2H), 1.80-1.23(m, 15H), 0.95(t, J=7.2Hz, 3H), 0.95(m, 2H).
실시예 40(62)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-메틸피페라진-1-일메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·3염산염
TLC: Rf 0.69(클로로포름:메탄올=5:1);
NMR(CD3OD): δ 7.74(s, 4H), 4.54(s, 2H), 4.41(s, 2H), 4.03(dd, J=7.5, 4.5Hz, 1H), 3.87-3.42(m, 14H), 3.00(s, 3H), 2.61-2.46(m, 2H), 2.21-2.07(m, 2H), 1.79-1.15(m, 15H), 1.02-0.92(m, 2H), 0.94(t, J=7.2Hz, 3H).
실시예 40(63)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(피리딘-1-옥사이드-3-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.42(클로로포름:메탄올=9:1);
NMR(CD3OD): δ 8.45(t, J=1.8Hz, 1H), 8.37(brd, J=6.3Hz, 1H), 7.71(dd, J=8.4, 6.3Hz, 1H), 7.72(d, J=8.7Hz, 2H), 7.59(brdd, J=8.4, 1.8Hz, 1H), 7.31(d, J=8.7Hz, 2H), 4.40(s, 2H), 4.04(dd, J=7.8Hz, 1H), 3.90-3.74(m, 2H), 3.57-3.40(m, 4H), 2.58-2.40(m, 2H), 2.28-2.08(m, 2H), 1.82-1.14(m, 15H), 1.04-0.90(m, 5H).
실시예 40(64)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-페닐설포닐페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.77(초산에틸:메탄올=9:1);
NMR(CD3OD): δ 8.08(d, J=8.4Hz, 2H), 8.02-7.96(m, 2H), 7.80(d, J=8.4Hz, 2H), 7.70-7.55(m, 3H), 4.43(s, 2H), 4.02(dd, J=7.8, 4.8Hz, 1H), 3.89-3.73(m, 2H), 3.49-3.34(m, 4H), 2.48-2.33(m, 2H), 2.23-2.04(m, 2H), 1.82-1.14(m, 15H), 1.03-0.85(m, 5H).
실시예 40(65)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-시클로헥실피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.32(초산에틸:메탄올=9:1);
NMR(CD3OD): δ 4.42-4.28(m, 1H), 4.28(s, 2H), 4.04(dd, J=7.5, 4.5Hz, 1H), 3.90-3.72(m, 2H), 3.60-3.43(m, 4H), 2.68-2.50(m, 2H), 2.50(s, 3H), 2.46(s, 3H), 2.25-2.06(m, 2H), 2.04-1.15(m, 25H), 1.05-0.89(m, 5H).
실시예 40(66)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(3-카르복시페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.16(초산에틸:메탄올=9:1);
NMR(CD3OD): δ 7.83(ddd, J=7.8, 1.5, 1.2Hz, 1H), 7.60(dd, J=2.4, 1.5Hz, 1H), 7.57(d, J=8.7Hz, 2H), 7.51(t, J=7.8Hz, 1H), 7.29(ddd, J=7.8, 2.4, 1.2Hz, 1H), 7.12(d, J=8.7Hz, 2H), 4.35(s, 2H), 4.04(dd, J=7.5, 4.5Hz, 1H), 3.90-3.74(m, 2H), 3.58-3.35(m, 4H), 2.49-2.34(m, 2H), 2.28-2.09(m, 2H), 1.93-1.10(m, 15H), 1.07-0.85(m, 5H).
실시예 40(67)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(피페리딘-1-일메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.56(클로로포름:메탄올=9:1);
NMR(CD3OD): δ 7.75(d, J=8.4Hz, 2H), 7.64(d, J=8.4Hz, 2H), 4.40(s, 2H), 4.34(s, 2H), 4.03(dd, J=7.8, 4.8Hz, 1H), 3.90-3.72(m, 2H), 3.53-3.38(m, 6H), 3.05-2.91(m, 2H), 2.66-2.49(m, 2H), 2.24-2.04(m, 2H), 2.00-1.13(m, 21H), 1.04-0.86(m, 5H).
실시예 40(68)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-(피롤리딘-1-일설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.40(초산에틸:메탄올=9:1);
NMR(CD3OD): δ 8.01(d, J=8.7Hz, 2H), 7.76(d, J=8.7Hz, 2H), 4.32(s, 2H), 4.05(dd, J=7.5, 4.5Hz, 1H), 3.94-3.75(m, 2H), 3.66-3.56(m, 2H), 3.49-3.41(m, 2H), 3.32-3.25(m, 4H), 2.60-2.46(m, 2H), 2.48(s, 3H), 2.40(s, 3H), 2.30-2.11(m, 2H), 1.83-1.14(m, 19H), 1.05-0.87(m, 5H).
실시예 40(69)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2,3-디히드로벤조푸란-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.61(초산에틸:메탄올=9:1);
NMR(CD3OD): δ 7.39(d, J=1.8Hz, 1H), 7.26(dd, J=8.4, 1.8Hz, 1H), 6.81(d, J=8.4Hz, 1H), 4.59(t, J=8.7Hz, 2H), 4.26(s, 2H), 4.04(dd, J=7.8, 4.8Hz, 1H), 3.84-3.67(m, 2H), 3.54-3.34(m, 4H), 3.25(t, J=8.7Hz, 2H), 2.48-2.31(m, 2H), 2.26-2.07(m, 2H), 1.83-1.14(m, 15H), 1.04-0.87(m, 5H).
실시예 40(70)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-카르복시페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.55(초산에틸:메탄올=9:1);
NMR(CD3OD): δ 8.04(d, J=8.7Hz, 2H), 7.61(d, J=8.7Hz, 2H), 7.18(d, J=8.7Hz, 2H), 7.07(d, J=8.7Hz, 2H), 4.38(s, 2H), 4.05(dd, J=7.8, 4.8Hz, 1H), 3.91-3.74(m, 2H), 3.57-3.35(m, 4H), 2.50-2.33(m, 2H), 2.29-2.09(m, 2H), 1.84-1.14(m, 15H), 1.05-0.86(m, 5H).
실시예 40(71)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-(2-히드록시에틸아미노설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.38(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.03(d, J=8.7Hz, 2H), 7.72(d, J=8.7Hz, 2H), 4.31(s, 2H), 4.05(dd, J=7.5, 4.5Hz, 1H), 3.94-3.74(m, 2H), 3.66-3.56(m, 2H), 3.56(t, J=5.7Hz, 2H), 3.51-3.41(m, 2H), 3.01(t, J=5.7Hz, 2H), 2.63-2.43(m, 2H), 2.47(s, 3H), 2.40(s, 3H), 2.32-2.10(m, 2H), 1.93-1.10(m, 15H), 1.06-0.93(m, 2H), 0.96(t, J=7.2Hz, 3H).
실시예 40(72)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-(2-디메틸아미노에틸아미노설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·3염산염
TLC: Rf 0.13(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.07(d, J=8.7Hz, 2H), 7.79(d, J=8.7Hz, 2H), 4.31(s, 2H), 4.04(dd, J=7.5, 4.2Hz, 1H), 3.82-3.76(m, 2H), 3.68-3.48(m, 4H), 3.34-3.24(m, 4H), 2.95(s, 6H), 2.76-2.52(m, 2H), 2.50(s, 3H), 2.43(s, 3H), 2.25-2.08(m, 2H), 1.82-1.14(m, 15H), 1.02-0.88(m, 5H).
실시예 40(73)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(1-히드록시-1-페닐메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.30(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.62-7.18(m, 9H), 5.82(s, 1H), 4.34(s, 2H), 4.03(dd, J=7.5, 4.5Hz, 1H), 3.88-3.72(m, 2H), 3.58-3.30(m, 4H), 2.42-2.04(m, 4H), 1.82-1.24(m, 15H), 0.94(t, J=7.2Hz, 3H), 0.94(m, 2H).
실시예 40(74)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(카르복시메틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.30(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.47(d, J=8.7Hz, 2H), 7.04(d, J=8.7Hz, 2H), 4.70(s, 2H), 4.29(s, 2H), 4.03(dd, J=7.5, 4.5Hz, 1H), 3.86-3.69(m, 2H), 3.54-3.33(m, 4H), 2.44-2.28(m, 2H), 2.26-2.06(m, 2H), 1.83-1.12(m, 15H), 1.04-0.85(m, 5H).
실시예 40(75)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-히드록시피페리딘-1-일메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.17(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.76(d, J=7.8Hz, 2H), 7.70-7.61(m, 2H), 4.40(s, 2H), 4.38-4.32(m, 2H), 4.10-4.05(m, 1H), 4.03(dd, J=7.5, 4.5Hz, 1H), 3.90-3.68(m, 2H), 3.56-3.40(m, 4H), 3.18-3.00(m, 1H), 2.70-2.48(m, 2H), 2.23-1.82(m, 5H), 1.82-1.10(m, 19H), 1.06-0.83(m, 2H), 0.94(t, J=7.2Hz, 3H).
실시예 40(76)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(3-카르복시페닐메틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.57(클로로포름:메탄올=5:1);
NMR(CD3OD): δ 8.10(s, 1H), 7.98(d, J=7.8Hz, 1H), 7.68(d, J=7.8Hz, 1H), 7.50(t, J=7.8Hz, 1H), 7.46(d, J=8.7Hz, 2H), 7.13(d, J=8.7Hz, 2H), 5.22(s, 2H), 4.28(s, 2H), 4.04(dd, J=7.8, 4.8Hz, 1H), 3.84-3.68(m, 2H), 3.52-3.32(m, 4H), 2.42-2.08(m, 4H), 1.82-1.16(m, 15H), 0.95(t, J=7.8Hz, 3H), 0.95(m, 2H).
실시예 40(77)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(1,4-벤조디옥산-6-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.41(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.48(d, J=9.0Hz, 2H), 7.02(d, J=9.0Hz, 2H), 6.86(m, 1H), 6.55-6.51(m, 2H), 4.31(s, 2H), 4.24(s, 4H), 4.05(dd, J=7.5, 4.5Hz, 1H), 3.86-3.70(m, 2H), 3.58-3.36(m, 4H), 2.42-2.08(m, 4H), 1.82-1.12(m, 15H), 0.96(t, J=7.2Hz, 3H), 0.96(m, 2H).
실시예 40(78)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3-(3-히드록시페닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.24(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.81(s, 1H), 7.74(m, 1H), 7.60-7.50(m, 2H), 7.28(m, 1H), 7.15-7.08(m, 2H), 6.82(m, 1H), 4.43(s, 2H), 4.04(dd, J=7.5, 4.5Hz, 1H), 3.86-3.78(m, 2H), 3.58-3.34(m, 4H), 2.48-2.08(m, 4H), 1.84-1.12(m, 15H), 0.95(t, J=7.2Hz, 3H), 0.95(m, 2H).
실시예 40(79)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(메틸설포닐아미노)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.40(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.53(d, J=8.4Hz, 2H), 7.34(d, J=8.4Hz, 2H), 4.32(s, 2H), 4.03(dd, J=7.8, 4.8Hz, 1H), 3.86-3.72(m, 2H), 3.52-3.34(m, 4H), 3.01(s, 3H), 2.50-2.32(m, 2H), 2.24-2.06(m, 2H), 1.82-1.10(m, 15H), 1.02-0.86(m, 5H).
실시예 40(80)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(6-(4-메톡시페닐)피리딘-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.67(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.26(m, 1H), 8.02(m, 1H), 7.08-6.84(m, 5H), 4.38(s, 2H),4.04(dd, J=7.8, 4.8Hz, 1H), 3.90-3.72(m, 2H), 3.81(s, 3H), 3.56-3.44(m, 2H), 3.42-3.32(m, 2H), 2.50-2.30(m, 2H), 2.30-2.08(m, 2H), 1.82-1.14(m, 15H), 1.02-0.88(m, 5H).
실시예 40(81)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-메틸아미노카르보닐페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.46(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.39(br d, J=4.5Hz, 1H), 7.84(d, J=9.0Hz, 2H), 7.58(d, J=8.4Hz, 2H), 7.15(d, J=8.4Hz, 2H), 7.07(d, J=9.0Hz, 2H), 4.35(s, 2H), 4.04(m, 1H), 3.85-3.74(m, 2H), 3.53-3.38(m, 4H), 2.91(d, J=4.5Hz, 3H), 2.55-2.30(m, 2H), 2.30-2.10(m, 2H), 1.80-1.10(m, 15H), 1.10-0.90(m, 2H), 0.95(t, J=7.2Hz, 3H).
실시예 40(82)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-클로로페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.76(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.52(d, J=9.0Hz, 2H), 7.38(d, J=9.0Hz, 2H), 7.09(d, J=9.0Hz, 2H), 7.02(d, J=9.0Hz, 2H), 4.32(s, 2H), 4.04(m, 1H), 3.90-3.70(m, 2H), 3.60-3.30(m, 4H), 2.50-2.10(m, 4H), 1.90-1. 10(m, 15H), 1.10-0.90(m, 2H), 0.95(t, J=7.5Hz, 3H).
실시예 40(83)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-비스(메틸설포닐)아미노페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.60(클로로포름:메탄올=5:1);
NMR(CD3OD): δ 7.69(d, J=8.4Hz, 2H), 7.60(d, J=8.4Hz, 2H), 4.41(s, 2H), 4.05(dd, J=7.8, 4.8Hz, 1H), 3.92-3.70(m, 2H), 3.56-3.36(m, 4H), 3.47(s, 6H), 2.46-2.08(m, 4H), 1.84-1.16(m, 15H), 0.96(t, J=7.5Hz, 3H), 0.96(m, 2H).
실시예 40(84)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3-(4-카르복시페닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.60(클로로포름:메탄올=5:1);
NMR(CD3OD): δ 8.13(d, J=9.0Hz, 2H), 7.95(s, 1H), 7.84(m, 1H), 7.82(d, J=9.0Hz, 2H), 7.66-7.61(m, 2H), 4.46(s, 2H), 4.04(dd, J=7.5, 4.5Hz, 1H), 3.96-3.78(m, 2H), 3.62-3.36(m, 4H), 2.54-2.32(m, 2H), 2.28-2.08(m, 2H), 1.82-1.08(m, 15H), 0.95(t, J=7.2Hz, 3H), 0.95(m, 2H).
실시예 40(85)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(페닐아미노카르보닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.25(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.07(d, J=8.1Hz, 2H), 7.73-7.67(m, 2H), 7.71(d, J=8.1Hz, 2H), 7.38(t, J=7.5Hz, 2H), 7.17(t, J=7.5Hz, 1H), 4.45(s, 2H), 4.05(dd, J=7.8, 4.8Hz, 1H), 3.92-3.72(m, 2H), 3.58-3.36(m, 4H), 2.50-2.08(m, 4H), 1.84-1.08(m, 15H), 0.96(t, J=7.8Hz, 3H), 0.96(m, 2H).
실시예 40(86)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-메틸티오페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.48(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.54(d, J=8.7Hz, 2H), 7.33(d, J=8.7Hz, 2H), 7.06(d, J=8.7Hz, 2H), 7.00(d, J=8.7Hz, 2H), 4.34(s, 2H), 4.05(dd, J=7.5, 4.5Hz, 1H), 3.86-3.70(m, 2H), 3.56-3.36(m, 4H), 2.48(s, 3H), 2.48-2.32(m, 2H), 2.28-2.08(m, 2H), 1.82-1.14(m, 15H), 0.96(t, J=7.2Hz, 3H), 0.96(m, 2H).
실시예 40(87)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-(2-디메틸아미노에틸아미노카르보닐)페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.11(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.94(d, J=9.0Hz, 2H), 7.64(d, J=8.7Hz, 2H), 7.15(d, J=8.7Hz, 2H), 7.10(d, J=9.0Hz, 2H), 4.36(s, 2H), 4.04(dd, J=7.8, 4.8Hz, 1H), 3.88-3.72(m, 4H), 3.52-3.36(m, 6H), 2.98(s, 6H), 2.62-2.44(m, 2H), 2.24-2.08(m, 2H), 1.80-1.10(m, 15H), 1.00-0.88(m, 5H).
실시예 40(88)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-아미노카르보닐페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.19(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.98(d, J=8.4Hz, 2H), 7.68(d, J=8.4Hz, 2H), 4.43(s, 2H), 4.03(dd, J=7.5, 4.8Hz, 1H), 3.92-3.76(m, 2H), 3.54-3.28(m, 4H), 2.52-2.36(m, 2H), 2.24-2.08(m, 2H), 1.82-1.10(m, 15H), 1.02-0.88(m, 5H).
실시예 40(89)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(디메틸아미노카르보닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.33(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.67(d, J=8.1Hz, 2H), 7.54(d, J=8.1Hz, 2H), 4.41(s, 2H),4.04(dd, J=7.5, 4.2Hz, 1H), 3.92-3.76(m, 2H), 3.54-3.32(m, 4H), 3.11(s, 3H), 2.99(s, 3H), 2.52-2.32(m, 2H), 2.26-2.08(m, 2H), 1.82-1.10(m, 15H), 1.02-0.86(m, 5H).
실시예 40(90)
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
TLC: Rf 0.73(클로로포름:메탄올=10:1);
NMR(CDCl3): δ 7.37-7.25(m, 4H), 7.10(m, 1H), 7.04-6.98(m, 2H), 6.96(d, J=8.7Hz, 2H), 5.81(brs, 1H), 3.99(m, 1H), 3.52(s, 2H), 3.52-3.32(m, 2H), 2.92-2.74(m, 3H), 2.57(dt, J=12.0, 3.0Hz, 1H), 2.18-1.88(m, 5H), 1.76-1.13(m, 14H), 1.07-0.88(m, 2H), 0.93(t, J=7.5Hz, 3H).
실시예 41
참고예 2에서 제조한 수지(3), N-알릴옥시카르보닐-4-피페리돈, n-부틸아민 및 (2R*,3R*)-N-(t-부틸옥시카르보닐)-2-아미노-3-히드록시-4-메틸펜탄산을 이용하여 참고예 3→참고예 4와 동일한 조작을 하고, 또한 1,4-벤조디옥산-6-카르복시알데히드를 이용하여 참고예 5→참고예 6→실시예 1과 동일한 조작을 하여 이하의 본 발명 화합물 (1) 및 (2)를 각각 얻었다.
실시예 41(1)
1-부틸-2,5-디옥소-3-(1-히드록시-2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
상기 식에서 *은 syn체와 anti체가 2:3의 비율로 혼합하고 있는 것을 나타낸다.
TLC: Rf 0.47(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.04(d, J=2.1Hz, 1H), 6.97(dd, J=8.4, 2.1Hz, 1H), 6.93(d, J=8.4Hz, 1H), 4.26(s, 4H), 4.23(s, 2H), 4.13(d, J=2.1Hz, 0.6H), 4.08(d, J=1.2Hz, 0.4H), 4.05-3.90(m, 1H), 3.76-3.63(m, 1H), 3.62-3.35(m, 3.4H), 3.19(dd, J=9.6, 2.1Hz, 0.6H), 3.20-3.10(m, 1H), 2.55-2.33(m, 2H), 2.30-1.95(m, 3H), 1.80-1.60(m, 1H), 1.55-1.25(m, 3H), 1.05-0.89(m, 9H).
실시예 41(2)
(Z)-1-부틸-2,5-디옥소-3-(2-메틸프로필리덴)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.52(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.04(d, J=2.1Hz, 1H), 6.97(dd, J=8.4, 2.1Hz, 1H), 6.93(d, J=8.4Hz, 1H), 5.84(d, J=10.5Hz, 1H), 4.26(s, 4H), 4.23(s, 2H), 3.72-3.55(m, 2H), 3.53-3.35(m, 4H), 2.80-2.60(m, 1H), 2.43-2.26(m, 2H), 2.25-2.15(m, 2H), 1.62-1.48(m, 2H), 1.45-1.30(m, 2H), 1.04(d, J=6.6Hz, 6H), 0.95(t, J=7.5Hz, 3H).
실시예 41(3)∼41(5)
(2R*,3R*)-N-(t-부틸옥시카르보닐)-2-아미노-3-히드록시-4-메틸펜탄산 대신에 해당하는 화합물을, 1,4-벤조디옥산-6-카르복시알데히드 대신에 해당하는 화합물을 이용하여 실시예 41과 동일한 조작을 하여 이하의 본 발명 화합물을 얻었다.
실시예 41(3)
(3S)-1-부틸-2,5-디옥소-3-((1R)-1-히드록시에틸)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.39(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.54(d, J=8.7Hz, 2H), 7.43-7.35(m, 2H), 7.21-7.14(m, 1H), 7.08-7.00(m, 4H), 4.32(s, 2H), 4.19(dq, J=1.5, 6.9Hz, 1H), 4.10-3.97(m, 1H), 3.78(d, J=1.5Hz, 1H), 3.72-3.51(m, 2H), 3.51-3.40(m, 2H), 3.28-3.14(m, 1H), 2.57-2.42(m, 2H), 2.40-2.25(m, 1H), 2.21-2.10(m, 1H), 1.81-1.60(m, 1H), 1.50-1.30(m, 3H), 1.22(d, J=6.9Hz, 3H), 0.95(t, J=7.2Hz, 3H).
실시예 41(4)
(Z)-1-부틸-2,5-디옥소-3-에틸리덴-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.29(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.53(d, J=9.0Hz, 2H), 7.43-7.35(m, 2H), 7.18(t, J=7.5Hz, 1H), 7.09-7.00(m, 4H), 6.08(q, J=7.5Hz, 1H), 4.33(s, 2H), 3.76-3.61(m, 2H), 3.57-3.40(m, 4H), 2.45-2.30(m, 2H), 2.28-2.15(m, 2H), 1.77(d, J=7.5Hz, 3H), 1.62-1.46(m, 2H), 1.44-1.28(m, 2H), 0.96(t, J=7.5Hz, 3H).
실시예 41(5)
(Z)-1-부틸-2,5-디옥소-3-(2-메틸프로필리덴)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.42(클로로포름:메탄올=20:1);
NMR(CD3OD): δ 7.51(d, J=8.7Hz, 2H), 7.43-7.35(m, 2H), 7.18(t, J=7.5Hz, 1H), 7.06(d, J=8.7Hz, 2H), 7.08-7.01(m, 2H), 5.85(d, J=10.5Hz, 1H), 4.34(s, 2H), 3.78-3.64(m, 2H), 3.57-3.40(m, 4H), 2.78-2.62(m, 1H), 2.43-2.18(m, 4H), 1.62-1.48(m, 2H), 1.46-1.30(m, 2H), 1.04(d, J=6.6Hz, 6H), 0.96(t, J=7.5Hz, 3H).
실시예 42
(3R
*
)-1-부틸-2,5-디옥소-3-((1R
*
)-1-히드록시-2-메틸프로필)-9-벤질옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸
N-(t-부틸옥시카르보닐)-L-류신 대신에 (2R*,3R*)-N-(t-부틸옥시카르보닐)-2-아미노-3-히드록시-4-메틸펜탄산을 이용하여 실시예 35와 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.43(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.39-7.30(m, 5H), 5.13(br, 2H), 4.12(d, J=2.5Hz, 1H), 4.10-4.00(m, 2H), 3.76-3.50(m, 2H), 3.39-3.25(m, 2H), 3.10-2.94(m, 1H), 2.18(m, 1H), 2.08-1.83(m, 4H), 1.70-1.56(m, 1H), 1.45-1.15(m, 3H), 1.01-0.89(m, 9H).
실시예 43
(3R
*
)-1-부틸-2,5-디옥소-3-((1R
*
)-1-히드록시-2-메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸·염산염
실시예 42에서 제조한 화합물을 이용하여 실시예 9와 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.08(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 4.15(d, J=2.0Hz, 1H), 3.96(dt, J=13.0, 4.0Hz, 1H), 3.71(dt, J=13.0, 4.0Hz, 1H), 3.57-3.47(m, 1H), 3.40-3.34(m, 2H), 3.23-3.12(m, 2H), 2.47-2.30(m, 2H), 2.25-1.98(m, 3H), 1.79-1.66(m, 1H), 1.52-1.28(m, 3H), 1.07-0.94(m, 9H).
실시예 44(1)∼44(13)
실시예 43에서 제조한 화합물과 해당하는 알데히드 화합물을 이용하여 실시예 10과 동일한 조작을 하여 이하에 도시한 본 발명 화합물을 얻었다.
실시예 44(1)
(3R
*
)-1-부틸-2,5-디옥소-3-((1R
*
)-1-히드록시-2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.51(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.52(d, J=8.7Hz, 2H), 7.44-7.35(m, 2H), 7.18(t, J=7.5Hz, 1H), 7.10-7.00(m, 4H), 4.33(s, 2H), 4.14(d, J=2.1Hz, 1H), 4.06-3.93(m, 1H), 3.80-3.67(m, 1H), 3.56-3.40(m, 3H), 3.19(dd, J=9.3, 2.1Hz, 1H), 3.20-3.10(m, 1H), 2.53-2.35(m, 2H), 2.35-2.20(m, 1H), 2.19-2.08(m, 1H), 2.07-1.91(m, 1H), 1.80-1.70(m, 1H), 1.50-1.25(m, 3H), 0.99(d, J=6.6Hz, 3H), 0.97(d, J=6.6Hz, 3H), 0.95(t, J=7.2Hz, 3H).
실시예 44(2)
(3R
*
)-1-부틸-2,5-디옥소-3-((1R
*
)-1-히드록시-2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.38(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.60-7.45(m, 5H), 4.30(s, 2H), 4.15(d, J=2.4Hz, 1H), 4.05(m, 1H), 3.79(m, 1H), 3.62-3.48(m, 3H), 3.29-3.16(m, 2H), 2.60-2.45(m, 2H), 2.44-2.30(m, 7H), 2.17(m, 1H), 2.01(m, 1H), 1.70(m, 1H), 1.51-1.31(m, 3H), 1.03-0.91(m, 9H).
실시예 44(3)
(3R
*
)-1-부틸-2,5-디옥소-3-((1R
*
)-1-히드록시-2-메틸프로필)-9-(6-페닐옥시피리딘-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.51(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.39(d, J=2.1Hz, 1H), 8.16(dd, J=8.4, 2.1Hz, 1H), 7.46(t, J=7.8Hz, 2H), 7.29(t, J=7.8Hz, 1H), 7.17(d, J=7.8Hz, 2H), 7.08(d, J=8.4Hz, 1H), 4.40(s, 2H), 4.13(d, J=2.1 Hz , 1H), 4.07-3.94(m, 1H), 3.83-3.69(m, 1H), 3.60-3.42(m, 3H), 3.29-3.22(m, 1H), 3.19(dd, J=9.6, 2.1Hz, 1H), 2.62-2.32(m, 3H), 2.18-2.07(m, 1H), 2.06-1.94(m, 1H), 1.78-1.60(m, 1H), 1.50-1.31(m, 3H), 1.07-0.87(m, 9H).
실시예 44(4)
(3R
*
)-1-부틸-2,5-디옥소-3-((1R
*
)-1-히드록시-2-메틸프로필)-9-(4-(4-메틸페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.46(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.47(d, J=8.7Hz, 2H), 7.20(d, J=8.7Hz, 2H), 7.02(d, J=8.7Hz, 2H), 6.92(d, J=8.7Hz, 2H), 4.29(s, 2H), 4.14(d, J=2.1Hz, 1H), 3.97(m, 1H), 3.72(m, 1H), 3.56-3.39(m, 2H), 3.25-3.09(m, 3H), 2.53-2.08(m, 7H), 2.01(m, 1H), 1.70(m, 1H), 1.48-1.28(m, 3H), 1.05-0.88(m, 9H).
실시예 44(5)
(3R
*
)-1-부틸-2,5-디옥소-3-((1R
*
)-1-히드록시-2-메틸프로필)-9-(4-시클로헥실옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.43(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.40(d, J=8.7Hz, 2H), 7.00(d, J=8.7Hz, 2H), 4.37(m, 1H), 4.24(brs, 2H), 4.13(d, J=2.1Hz, 1H), 3.94(m, 1H), 3.68(m, 1H), 3.52-3.34(m, 2H), 3.29-3.07(m, 3H), 2.52-1.92(m, 7H), 1.8 5-1.27(m, 12H), 1.04-0.89(m, 9H).
실시예 44(6)
(3R
*
)-1-부틸-2,5-디옥소-3-((1R
*
)-1-히드록시-2-메틸프로필)-9-(4-(테트라히드로피란-4-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.20(초산에틸:메탄올=10:1);
NMR(CD3OD): δ 7.45(d, J=8.7Hz, 2H), 7.06(d, J=8.7Hz, 2H), 4.67-4.59(m,1H), 4.28(s, 2H), 4.13(d, J=2.5Hz, 1H), 4.00-3.90(m, 3H), 3.75-3.67(m, 1H), 3.63-3.53(m, 2H), 3.50-3.41(m, 3H), 3.18(dd, J=9.0, 2.0Hz, 1H), 3.18(m, 1H), 2.49-1.96(m, 7H), 1.77-1.65(m, 3H), 1.44-1.30(m, 3H), 0.98(d, J=6.5Hz, 3H), 0.96(d, J=6.5Hz, 3H), 0.94(t, J=7.2Hz, 3H).
실시예 44(7)
(3R
*
)-1-부틸-2,5-디옥소-3-((1R
*
)-1-히드록시-2-메틸프로필)-9-(4-(피리딘-3-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.22(초산에틸:메탄올=10:1);
NMR(CD3OD): δ 8.76(d, J=2.5Hz, 1H), 8.63(d, J=6.0Hz, 1H), 8.29(dd, J=9.0, 2.5Hz, 1H), 8.08(dd, J=9.0, 6.0Hz, 1H), 7.77(d, J=9.0Hz, 2H), 7.35(d, J=9.0Hz, 2H), 4.41(s, 2H), 4.14(d, J=2. 0Hz, 1H), 4.00(m, 1H), 3.76(m, 1H), 3.61-3.47(m, 3H), 3.20(dd, J=9.5, 2.0Hz, 1H), 3.20(m, 1H), 2.62(m, 1H), 2.46(m, 2H), 2.10(m, 1H), 2.05-1.95(m, 1H), 1.69(m, 1H), 1.41-1.35(m, 3H), 0.99(d, J=6.5Hz, 3H), 0.97(d, J=6.5Hz, 3H), 0.95(t, J=7.5Hz, 3H).
실시예 44(8)
(3R
*
)-1-부틸-2,5-디옥소-3-((1R
*
)-1-히드록시-2-메틸프로필)-9-(4-이소프로필페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.55(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.47(d, J=8.1Hz, 2H), 7.37(d, J=8.1Hz, 2H), 4.31(s, 2H), 4.13(d, J=2.1Hz, 1H), 4.05-3.91(m, 1H), 3.80-3.65(m, 1H), 3.57-3.38(m, 3H), 3.26-3.13(m, 1H), 3.19(dd, J=9.3, 2.1Hz, 1H), 3.03-2.86(m, 1H), 2.53-2.38(m, 2H), 2.38-2.23(m, 1H), 2.16-2.05(m, 1H), 2.06-1.92(m, 1H), 1.77-1.56(m, 1H), 1.49-1.26(m, 3H), 1.25(d, J=6.9Hz, 6H), 0.98(d, J=6.6Hz, 3H), 0.97(d, J=6.6Hz, 3H), 0.94(t, J=7.2Hz, 3H).
실시예 44(9)
(3R
*
)-1-부틸-2,5-디옥소-3-((1R
*
)-1-히드록시-2-메틸프로필)-9-(3,5-디메틸-1-(4-메틸페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.49(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.40(s, 4H), 4.33(s, 2H), 4.15(d, J=2.1Hz, 1H), 4.11-3.97(m, 1H), 3.86-3.72(m, 1H), 3.64-3.50(m, 3H), 3.39-3.30(m, 1H), 3.21(dd, J=9.3, 2.1Hz, 1H), 2.72-2.55(m, 1H), 2.53-2.40(m, 2H), 2.46(s, 3H), 2.44(s, 3H), 2.40(s, 3H), 2.18-2.07(m, 1H), 2.07-1.96(m, 1H), 1.78-1.60(m, 1H), 1.50-1.30(m, 3H), 1.00(d, J=6.6Hz, 3H), 0.98(d, J=6.6Hz, 3H), 0.95(t, J=7.2Hz, 3H).
실시예 44(10)
(3R
*
)-1-부틸-2,5-디옥소-3-((1R
*
)-1-히드록시-2-메틸프로필)-9-(3-메틸-5-클로로-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.56(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.58-7.47(m, 5H), 4.33(s, 2H), 4.15(d, J=2.1Hz, 1H), 4.15-4.02(m, 1H), 3.89-3.75(m, 1H), 3.65-3.48(m, 3H), 3.30-3.20(m, 1H), 3.20(dd, J=9.6, 2.1Hz, 1H), 2.64-2.46(m, 2H), 2.44(s, 3H), 2.44-2.32(m, 1H), 2.21-2.10(m, 1H), 2.08-1.93(m, 1H), 1.80-1.60(m, 1H), 1.52-1.30(m, 3H), 0.99(d, J=6.6Hz, 3H), 0.98(d, J=6.6Hz, 3H), 0.96(t, J=7.2Hz, 3H).
실시예 44(11)
(3R
*
)-1-부틸-2,5-디옥소-3-((1R
*
)-1-히드록시-2-메틸프로필)-9-(4-(4-카르복시페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.29(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.04(d, J=9.0Hz, 2H), 7.60(d, J=8.7Hz, 2H), 7.18(d, J=8.7Hz, 2H), 7.07(d, J=9.0Hz, 2H), 4.37(s, 2H), 4.14(d, J=2.1Hz, 1H), 4.10-3.94(m, 1H), 3.83-3.69(m, 1H), 3.59-3.40(m, 3H), 3.25-3.12(m, 1H), 3.19(dd, J=9.3, 2.1Hz, 1H), 2.55-2.37(m, 2H), 2.37-2.22(m, 1H), 2.19-2.08(m, 1H), 2.08-1.94(m, 1H), 1.79-1.60(m, 1H), 1.52-1.26(m, 3H), 0.99(d, J=6.6Hz, 3H),0.97(d, J=6.6Hz, 3H), 0.95(t, J=7.2Hz, 3H).
실시예 44(12)
(3R
*
)-1-부틸-2,5-디옥소-3-((1R
*
)-1-히드록시-2-메틸프로필)-9-(3,5-디메틸-1-(피리딘-2-일)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.28(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 8.53(d, J=5.1Hz, 1H), 8.05(t, J=7.8Hz, 1H), 7.81(d, J=7.8Hz, 1H), 7.44(dd, J=7.8, 5.1Hz, 1H), 4.33(s, 2H), 4.16(d, J=2.1Hz, 1H), 4.06(m, 1H), 3.78(m, 1H), 3.62-3.44(m, 3H), 3.26(m, 1H), 3.21(dd, J=9.6, 2.1Hz, 1H), 2.68(s, 3H), 2.60-2.30(m, 3H), 2.42(s, 3H), 2.16(m, 1H), 2.02(m, 1H), 1.72(m, 1H), 1.50-1.26(m, 3H), 1.00(d, J=6.6Hz, 3H), 0.99(d, J=6.6Hz, 3H), 0.96(t, J=7.2Hz, 3H).
실시예 44(13)
(3R
*
)-1-부틸-2,5-디옥소-3-((1R
*
)-1-히드록시-2-메틸프로필)-9-(3,5-디메틸-1-(4-카르복시페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.25(클로로포름:메탄올:초산=20:2:1);
NMR(CD3OD): δ 8.19(d, J=8.7Hz, 2H), 7.62(d, J=8.7Hz, 2H), 4.32(s, 2H), 4.16(d, J=2.1Hz, 1H), 4.12-3.98(m, 1H), 3.87-3.74(m, 1H), 3.63-3.45(m, 3H), 3.30-3.10(m, 1H), 3.20(dd, J=9.3, 2.1Hz, 1H), 2.59-2.48(m, 2H), 2.44(s, 3H), 2.40-2.23(m, 1H), 2.39(s, 3H), 2.23-2.10(m, 1H), 2.10-1.96(m, 1H), 1.80-1.62(m, 1H), 1.52-1.24(m, 3H), 1.00(d, J=6.6Hz, 3H), 0.98(d, J=6.6Hz, 3H), 0.96(t, J=7.2Hz, 3H).
실시예 45
(3R
*
)-1-부틸-2,5-디옥소-3-((1R
*
)-1-히드록시-1-시클로헥실메틸)-9-벤질옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸
N-(t-부틸옥시카르보닐)-L-류신 대신에 (2R*,3R*)-N-(t-부틸옥시카르보닐)-2-아미노-3-히드록시-3-시클로헥실프로판산을 이용하여 실시예 35와 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.53(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.39-7.27(m, 5H), 5.13(m, 2H), 4.13(d, J=2.5Hz, 1H), 4.06-4.02(m, 2H), 3.78-3.48(m, 2H), 3.36-3.29(m, 2H), 3.02(br, 1H), 2.17(m, 1H), 2.03-1.58(m, 10H), 1.47-1.13(m, 6H), 1.02-0.89(m, 5H).
실시예 46
(3R
*
)-1-부틸-2,5-디옥소-3-((1R
*
)-1-히드록시-1-시클로헥실메틸)-1,4,9-트리아자스피로[5.5]운데칸
실시예 45에서 제조한 화합물을 이용하여 실시예 9와 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.33(클로로포름:메탄올:초산=20:6:1);
NMR(CD3OD): δ 4.13(d, J=2.5Hz, 1H), 3.48-3.22(m, 5H), 2.97-2.89(m, 2H), 2.12-1.65(m, 10H), 1.56-1.16(m, 7H), 1.03-0.85(m, 5H).
실시예 47(1)∼47(8)
실시예 46에서 제조한 화합물과 해당하는 알데히드 화합물을 이용하여 실시예 10과 동일한 조작을 하여 이하에 도시한 본 발명 화합물을 얻었다.
실시예 47(1)
(3R
*
)-1-부틸-2,5-디옥소-3-((1R
*
)-1-히드록시-1-시클로헥실메틸)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.44(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.55-7.51(m, 2H), 7.42-7.36(m, 2H), 7.18(tt, J=7.5, 1.0Hz, 1H), 7.08-7.01(m, 4H), 4.32(s, 2H), 4.15(d, J=2.0Hz, 1H), 3.98(dt, J=3.5, 12.5Hz, 1H), 3.73(dt, J=3.5, 12.5Hz, 1H), 3 . 57-3.39(m, 3H), 3.26(d, J=2.0Hz, 1H), 3.20(m, 1H), 2.52-2.39(m, 2H), 2.30(m, 1H), 2.12(d, J=15.5Hz, 1H), 2.04-1.92(m, 2H), 1.80-1.62(m, 5H), 1.48-1.11(m, 6H), 1.01-0.82(m, 5H).
실시예 47(2)
(3R
*
)-1-부틸-2,5-디옥소-3-((1R
*
)-1-히드록시-1-시클로헥실메틸)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.41(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.60-7.50(m, 5H), 4.33(s, 2H), 4.17(d, J=2.5Hz, 1H), 4.04(m, 1H), 3.85-3.75(m, 1H), 3.61-3.51(m, 3H), 3.35-3.27(m, 2H), 2.62(m, 1H), 2.49-2.44(m, 5H), 2.41(s, 3H), 2.15(m, 1H), 2.05-1.92(m, 2H), 1.77-1.65(m, 5H), 1.44-1.15(m, 6H), 1.01-0.85(m, 5H).
실시예 47(3)
(3R
*
)-1-부틸-2,5-디옥소-3-((1R
*
)-1-히드록시-1-시클로헥실메틸)-9-(4-이소프로필페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.69(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.48(d, J=8.4Hz, 2H), 7.36(d, J=8.4Hz, 2H), 4.31(s, 2H), 4.14(d, J=2.1Hz, 1H), 3.98(m, 1H), 3.72(m, 1H), 3.55-3.40(m, 3H), 3.29-3.16(m, 2H), 2.95(m, 1H), 2.52-2.24(m, 3H), 2.15-1.86(m, 3H), 1.80-1.60(m, 5H), 1.48-1.10(m, 6H), 1.25(d, J=6.9Hz, 6H), 1.02-0.82(m, 5H).
실시예 47(4)
(3R
*
)-1-부틸-2,5-디옥소-3-((1R
*
)-1-히드록시-1-시클로헥실메틸)-9-(4-(6-메틸피리딘-3-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.51(초산에틸:메탄올=10:1);
NMR(CD3OD): δ 8.59(d, J=2.7Hz, 1H), 8.19(dd, J=9.0, 2.7Hz, 1H), 7.91(d, J=9.0Hz, 1H), 7.75(d, J=8.4Hz, 2H), 7.30(d, J=8.4Hz, 2H), 4.39(s, 2H), 4.15(d, J=2.0Hz, 1H), 3.99(m, 1H), 3.73(m, 1H), 3.61-3.46(m, 3H), 3.37-3.26(m, 2H), 2.77(s, 3H), 2.62(m, 1H), 2.45(m, 1H), 2.13-1.92(m, 3H), 1.73(m, 4H), 1.40-1.14(m, 8H), 1.01-0.86(m, 2H), 0.95(t, J=7.0Hz, 3H).
실시예 47(5)
(3R
*
)-1-부틸-2,5-디옥소-3-((1R
*
)-1-히드록시-1-시클로헥실메틸)-9-(3,5-디메틸-1-(4-플루오로페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.49(초산에틸:메탄올=10:1);
NMR(CD3OD): δ 7.57(m, 2H), 7.37-7.31(m, 2H), 4.32(s, 2H), 4.16(d, J=2.0Hz, 1H), 4.08-4.00(m, 1H), 3.79(m, 1H), 3.63-3.52(m, 3H), 3.37-3.27(m, 2H), 2.65(m, 1H), 2.48(m, 1H), 2.45(s, 3H), 2.39(s, 3H), 2.16-1.92(m, 3H), 1.73(m, 4H), 1.42-1.15(m, 8H), 1.01-0.88(m, 2H), 0.95(t, J=7.0Hz, 3H).
실시예 47(6)
(3R
*
)-1-부틸-2,5-디옥소-3-((1R
*
)-1-히드록시-1-시클로헥실메틸)-9-(4-(4-메톡시페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.25(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.47(d, J=9.0Hz, 2H), 7.00(d, J=9.0Hz, 2H), 6.99-6.92(m, 4H), 4.30(s, 2H), 4.16(d, J=2.1Hz, 1H), 3.98(m, 1H), 3.80(s, 3H), 3.72(m, 1H), 3.58-3.38(m, 3H), 3.30-3.08(m, 2H), 2.54-1.88(m, 6H), 1.82-1.60(m, 5H), 1.50-1.10(m, 6H), 0.96(t, J=7.5Hz, 3H), 0.96(m, 2H).
실시예 47(7)
(3R
*
)-1-부틸-2,5-디옥소-3-((1R
*
)-1-히드록시-1-시클로헥실메틸)-9-(4-(4-플루오로페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.28(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.51(d, J=8.7Hz, 2H), 7.13(d, J=8.7Hz, 2H), 7.10-7.04(m, 4H), 4.33(s, 2H), 4.16(d, J=2.1Hz, 1H), 4.00(m, 1H), 3.72(m, 1H), 3.58-3.40(m, 3H), 3.30-3.08(m, 2H), 2.56-1.88(m, 6H), 1.82-1.60(m, 5H), 1.54-1.10(m, 6H), 0.96(t, J=7.2Hz, 3H), 0.96(m, 2H).
실시예 47(8)
(3R
*
)-1-부틸-2,5-디옥소-3-((1R
*
)-1-히드록시-1-시클로헥실메틸)-9-(4-(4-메틸설포닐아미노페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.52(초산에틸:메탄올=10:1);
NMR(CD3OD): δ 7.53(d, J=8.1Hz, 2H), 7.30(d, J=9.0Hz, 2H), 7.08(d, J=8.1Hz, 2H), 7.04(d, J=9.0Hz, 2H), 4.34(s, 2H), 4.16(d, J=2.1Hz, 1H), 4.00(m, 1H), 3.76(m, 1H), 3.58-3.42(m, 3H), 3.30-3.08(m, 2H), 2.96(s, 3H), 2.54-1.88(m, 6H), 1.82-1.62(m, 5H), 1.50-1.14(m, 6H), 0.96(t, J=7.2Hz, 3H), 0.96(m, 2H).
실시예 48
(3R
*
)-1-(2-부티닐)-2,5-디옥소-3-((1R
*
)-1-히드록시-1-시클로헥실메틸)-9-알릴옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸
참고예 2에서 제조한 수지(3), N-알릴옥시카르보닐-4-피페리돈, 2-부티닐아민, (2R*,3R*)-N-(t-부틸옥시카르보닐)-2-아미노-3-히드록시-3-시클로헥실프로판산을 이용하여 참고예 3→참고예 6→실시예 1과 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.32(클로로포름:메탄올=15:1);
NMR(CD3OD): δ 6.04-5.91(m, 1H), 5.35-5.27(m, 1H), 5.23-5.19(m, 1H), 4.60-4.58(m, 2H), 4.27(dq, J=17.5, 2.5Hz, 1H), 4.19(d, J=2.5Hz, 1H), 4.07-4.01(m, 2H), 3.89(dq, J=17.5, 2.5Hz, 1H), 3.75-3.50(m, 2H), 3.38(dd, J=9.0, 2.5Hz, 1H), 2.32-2.17(m, 2H), 2.07-1.70(m, 11H), 1.33-1.14(m, 3H), 1.00-0.85(m, 2H).
실시예 49
(3R
*
)-1-(2-부티닐)-2,5-디옥소-3-((1R
*
)-1-히드록시-1-시클로헥실메틸)-1,4,9-트리아자스피로[5.5]운데칸
실시예 48에서 제조한 화합물을 이용하여 참고예 4와 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.33(클로로포름:메탄올:초산=20:6:1);
NMR(CD3OD): δ 4.28(dq, J=17.5, 2.5Hz, 1H), 4.18(d, J=2.5Hz, 1H), 4.03(dq, J=17.5, 2.5Hz, 1H), 3.48-3.29(m, 3H), 2.99-2.90(m, 2H), 2.26-1.73(m, 14H), 1.32-1.18(m, 3H), 1.01-0.91(m, 2H).
실시예 50(1)∼50(6)
실시예 49에서 제조한 화합물과 해당하는 알데히드 화합물을 이용하여 실시예 10과 동일한 조작을 하여 이하에 도시한 본 발명 화합물을 얻었다.
실시예 50(1)
(3R
*
)-1-(2-부티닐)-2,5-디옥소-3-((1R
*
)-1-히드록시-1-시클로헥실메틸)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.37(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.60-7.50(m, 5H), 4.42-4.33(m, 3H), 4.21(d, J=2.5Hz,1H), 4.08-3.99(m, 2H), 3.85-3.75(m, 1H), 3.65-3.57(m, 2H), 3.32(m, 1H), 2.79(m, 1H), 2.48-2.43(m, 5H), 2.40(s, 3H), 2.22(m, 1H), 2.05-1.93(m, 2H), 1.80-1.64(m, 7H), 1.39-1.11(m, 3H), 1.03-0.84(m, 2H).
실시예 50(2)
(3R
*
)-1-(2-부티닐)-2,5-디옥소-3-((1R
*
)-1-히드록시-1-시클로헥실메틸)-9-(3,5-디메틸-1-(4-메틸페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.35(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.40(s, 4H), 4.45-4.30(m, 3H), 4.20(m, 1H), 4.16-3.98(m, 2H), 3.78(m, 1H), 3.68-3.56(m, 2H), 3.30(m, 1H), 2.82(m, 1H), 2.56-2.42(m, 8H), 2.39(s, 3H), 2.28-1.88(m, 3H), 1.80-1.60(m, 7H), 1.40-1.10(m, 3H), 1.12-0.82(m, 2H).
실시예 50(3)
(3R
*
)-1-(2-부티닐)-2,5-디옥소-3-((1R
*
)-1-히드록시-1-시클로헥실메틸)-9-(4-이소프로필페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.33(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.47(d, J=8.1Hz, 2H), 7.36(d, J=8.1Hz, 2H), 4.38-4.28(m, 3H), 4.17(m, 1H), 4.04-3.88(m, 2H), 3.74(m, 1H), 3.50-3.40(m, 2H), 3.28(m, 1H), 2.92(m, 1H), 2.64(m, 1H), 2.50-1.86(m, 5H), 1.80-1.62(m, 7H), 1.36-1.04(m, 3H), 1.25(d, J=7.2Hz, 6H), 1.00-0.82(m, 2H).
실시예 50(4)
(3R
*
)-1-(2-부티닐)-2,5-디옥소-3-((1R
*
)-1-히드록시-1-시클로헥실메틸)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.39(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.53(d, J=9.0Hz, 2H), 7.42-7.37(m, 2H), 7.17(t, J=7.5Hz, 1H), 7.06-7.02(m, 4H), 4.40-4.30(m, 3H), 4.18(m, 1H), 4.04-3.90(m, 2H), 3.72(m, 1H), 3.30-3.20(m, 2H), 3.28(m, 1H), 2.68(m, 1H), 2.52-1.86(m, 5H), 1.80-1.60(m, 7H), 1.38-1.10(m, 3H), 1.02-0.82(m, 2H).
실시예 50(5)
(3R
*
)-1-(2-부티닐)-2,5-디옥소-3-((1R
*
)-1-히드록시-1-시클로헥실메틸)-9-(4-(4-메틸페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.45(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.50(d, J=8.4Hz, 2H), 7.20(d, J=8.7Hz, 2H), 7.01(d, J=8.7Hz, 2H), 6.92(d, J=8.4Hz, 2H), 4.40-4.28(m, 3H), 4.18(m, 1H), 4.04-3.88(m, 2H), 3.74(m, 1H), 3.52-3.40(m, 2H), 3.26(m, 1H), 2.64(m, 1H), 2.54-1.86(m, 5H), 2.33(s, 3H), 1.80-1.62(m, 7H), 1.38-1.10(m, 3H), 1.02-0.82(m, 2H).
실시예 50(6)
(3R
*
)-1-(2-부티닐)-2,5-디옥소-3-((1R
*
)-1-히드록시-1-시클로헥실메틸)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.33(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.04(s, 1H), 6.99-6.91(m, 2H), 4.35(m, 1H), 4.27(s, 4H), 4.24(s, 2H), 4.18(m, 1H), 4.04-3.84(m, 2H), 3.70(m, 1H), 3.56-3.38(m, 2H), 3.28(m, 1H), 2.68-1.88(m, 6H), 1.80-1.60(m, 7H), 1.4 0-1.10(m, 3H), 1.02-0.80(m, 2H).
실시예 51
(3R
*
)-1-(2-부티닐)-2,5-디옥소-3-((1R
*
)-1-히드록시-2-메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸·초산염
(2R*,3R*)-N-(t-부틸옥시카르보닐)-2-아미노-3-히드록시-3-시클로헥실프로판산 대신에 (2R*,3R*)-N-(t-부틸옥시카르보닐)-2-아미노-3-히드록시-4-메틸펜탄산을 이용하여 실시예 48→실시예 49와 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.22(클로로포름:메탄올:초산=20:6:1);
NMR(CD3OD): δ 4.36(dq, J=17.0, 2.5Hz, 1H), 4.19(d, J=2.0Hz, 1H), 3.95-3.79(m, 2H), 3.62(dt, J=3.5, 13.0Hz, 1H), 3.34-3.26(m, 2H), 3.22(dd, J=9.5, 2.0Hz, 1H), 2.54-2.43(m, 1H), 2.37(m, 1H), 2.20-1.98(m, 3H), 1.91(s, 3H), 1.75(t, J=2.5Hz, 3H), 1.01-0.97(m, 6H).
실시예 52(1)∼52(5)
실시예 51에서 제조한 화합물과 해당하는 알데히드 화합물을 이용하여 실시예 10과 동일한 조작을 하여 이하에 도시한 본 발명 화합물을 얻었다.
실시예 52(1)
(3R
*
)-1-(2-부티닐)-2,5-디옥소-3-((1R
*
)-1-히드록시-2-메틸프로필)-9-(3,5-디메틸-1-(4-메틸페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.28(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.38(d, J=3.9Hz, 2H), 7.35(d, J=3.9Hz, 2H), 4.33(s, 2H), 4.20(d, J=2.1Hz, 1H), 4.10-3.90(m, 2H), 3.78(m, 1H), 3.68-3.52(m, 2H), 3.22(dd, J=9.3, 2.1Hz, 1H), 2.74(m, 1H), 2.54-2.20(m, 3H), 2.44(s, 3H), 2.40(s, 3H), 2.36(s, 3H), 1.98(m, 1H), 1.75(t, J=2.1Hz, 3H), 1.01(d, J=6.6Hz, 3H), 0.99(d, J=6.6Hz, 3H).
실시예 52(2)
(3R
*
)-1-(2-부티닐)-2,5-디옥소-3-((1R
*
)-1-히드록시-2-메틸프로필)-9-(4-(4-메틸페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.26(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.49(d, J=9.0Hz, 2H), 7.21(d, J=8.4Hz, 2H), 7.04(d, J=9.0Hz, 2H), 6.93(d, J=8.4Hz, 2H), 4.40(m, 1H), 4.34(s, 2H), 4.19(d, J=2.1Hz, 1H), 4.08-3.82(m, 2H), 3.76(m, 1H), 3.58-3.40(m, 2H), 3.20(dd, J=9.6, 2.1Hz, 1H), 2.72-2.42(m, 2H), 2.35(s, 3H), 2.35-2.18(m, 2H), 2.00(m, 1H), 1.74(t, J=2.1Hz, 3H), 1.00(d, J=6.6Hz, 3H), 0.98(d, J=6.6Hz, 3H).
실시예 52(3)
(3R
*
)-1-(2-부티닐)-2,5-디옥소-3-((1R
*
)-1-히드록시-2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.34(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.06-6.92(m, 3H), 4.38(m, 1H), 4.28(s, 4H), 4.25(s, 2H), 4.19(d, J=2.1Hz, 1H), 4.02-3.84(m, 2H), 3.70(m, 1H), 3.52-3.36(m, 2H), 3.20(dd, J=9.6, 2.1Hz, 1H), 2.60(m, 1H), 2.48(m, 1H), 2.32-2.16(m, 2H), 2.00(m, 1H), 1.74(t, J=2.1Hz, 3H), 1.00(d, J=6.6Hz, 3H), 0.98(d, J=6.6Hz, 3H).
실시예 52(4)
(3R
*
)-1-(2-부티닐)-2,5-디옥소-3-((1R
*
)-1-히드록시-2-메틸프로필)-9-(4-이소프로필페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.29(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.47(d, J=8.1Hz, 2H), 7.38(d, J=8.1Hz, 2H), 4.40(m, 1H), 4.33(s, 2H), 4.19(d, J=2.1Hz, 1H), 4.08-3.84(m, 2H), 3.76(m, 1H), 3.52-3.40(m, 2H), 3.20(dd, J=9.6, 2.1Hz, 1H), 2.96(m, 1H), 2.62(m, 1H), 2.48(m, 1H), 2.36-2.12(m, 2H), 2.00(m, 1H), 1.74(t, J=2.1Hz, 3H), 1.24(d, J=7.2Hz, 6H), 1.00(d, J=6.6Hz, 3H), 0.98(d, J=6.6Hz, 3H).
실시예 52(5)
(3R
*
)-1-(2-부티닐)-2,5-디옥소-3-((1R
*
)-1-히드록시-2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.24(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.52(d, J=9.0Hz, 2H), 7.41(t, J=7.2Hz, 2H), 7.19(t, J=7.2Hz, 1H), 7.09-7.03(m, 4H), 4.40(m, 1H), 4.35(s, 2H), 4.19(d, J=2.1Hz, 1H), 4.08-3.84(m, 2H), 3.78(m, 1H), 3.58-3.42(m, 2H), 3.21(dd, J=9.6, 2.1Hz, 1H), 2.72-2.42(m, 2H), 2.38-2.18(m, 2H), 2.00(m, 1H), 1.74(t, J=2.1Hz, 3H), 1.00(d, J=6.6Hz, 3H), 0.98(d, J=6.6Hz, 3H).
실시예 53
(3R
*
)-1-부틸-2,5-디옥소-3-((1S
*
)-1-히드록시-1-시클로헥실메틸)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸
참고예 2에서 제조한 수지(3), N-벤질-4-피페리돈, n-부틸아민, (2R*,3S*)-N-(t-부틸옥시카르보닐)-2-아미노-3-히드록시-3-시클로헥실프로판산을 이용하여 참고예 3→참고예 6→실시예 1과 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.33(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.40-7.20(m, 5H), 4.04(d, J=1.5Hz, 1H), 3.65-3.45(m, 2H), 3.57(s, 2H), 3.30(m, 1H), 3.05(m, 1H), 2.86-2.77(m, 3H), 2.30-2.00(m, 4H), 1.90-1.60(m, 6H), 1.60-1.10(m, 9H), 1.10-0.90(m, 2H), 0.95(t, J=7.2Hz, 3H).
실시예 54
(3R
*
)-1-부틸-2,5-디옥소-3-((1S
*
)-1-히드록시-1-시클로헥실메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
실시예 53에서 제조한 화합물을 이용하여 실시예9와 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.59(클로로포름:메탄올:초산=10:2:1);
NMR(CD3OD): δ 4.08(d, J=1.5Hz, 1H), 4.03(m, 1H), 3.70-3.12(m, 7H), 2.50-2.02(m, 5H), 1.85-1.66(m, 5H), 1.55-1.10(m, 7H), 1.10-0.85(m, 2H), 0.97(t, J=6.9Hz, 3H).
실시예 55(1)∼55(3)
실시예 54에서 제조한 화합물과 해당하는 알데히드 화합물을 이용하여 실시예 10과 동일한 조작을 하여 이하에 도시한 본 발명 화합물을 얻었다.
실시예 55(1)
(3R
*
)-1-부틸-2,5-디옥소-3-((1S
*
)-1-히드록시-1-시클로헥실메틸)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.46(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.50(d, J=8.7Hz, 2H), 7.39(dd, J=8.7, 7.5Hz, 2H), 7.17(t, J=7.5Hz, 1H), 7.09-7.00(m, 4H), 4.30(brs, 2H), 4.08(d, J=1.2Hz, 1H), 4.04(m, 1H), 3.74-3.36(m, 5H), 3.16(m, 1H), 2.55-2.33(m, 2H), 2.32-2.09(m, 2H), 2.04(m, 1H), 1.84-1.61(m, 5H), 1.53-1.12(m, 7H), 1.04-0.86(m, 5H).
실시예 55(2)
(3R
*
)-1-부틸-2,5-디옥소-3-((1S
*
)-1-히드록시-1-시클로헥실메틸)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.41(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.04(d, J=2.1Hz, 1H), 6.97(dd, J=8.1, 2.1Hz, 1H), 6.92(d, J=8.1Hz, 1H), 4.26(s, 4H), 4.21(s, 2H), 4.07(d, J=1.2Hz, 1H), 4.01(m, 1H), 3.70-3.34(m, 5H), 3.16(m, 1H), 2.53-2.32(m, 2H), 2.31-2.08(m, 2H), 2.03(m, 1H), 1.84-1.60(m, 5H), 1.52-1.12(m, 7H), 1.04-0.85(m, 5H).
실시예 55(3)
(3R
*
)-1-부틸-2,5-디옥소-3-((1S
*
)-1-히드록시-1-시클로헥실메틸)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.31(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.61-7.44(m, 5H), 4.31(s, 2H), 4.19-4.06(m, 2H), 3.73(m, 1H), 3.66-3.52(m, 4H), 3.26(m, 1H), 2.62-2.48(m, 2H), 2.45-2.30(m, 7H), 2.19(m, 1H), 2.04(m, 1H), 1.84-1.63(m, 5H), 1.54-1.12(m, 7H), 1.05-0.86(m, 5H).
실시예 56
(3S)-1-부틸-2,5-디옥소-3-((1S)-1-히드록시-2-메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸·염산염
(2R*,3R*)-N-(t-부틸옥시카르보닐)-2-아미노-3-히드록시-4-메틸펜탄산 대신에 (2S,3S)-N-(t-부틸옥시카르보닐)-2-아미노-3-히드록시-4-메틸펜탄산을 이용하여 실시예 42→실시예 43과 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.08(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 4.15(d, J=2.0Hz, 1H), 3.96(dt, J=13.0, 4.0Hz, 1H), 3.71(dt, J=13.0, 4.0Hz, 1H), 3.57-3.47(m, 1H), 3.40-3.34(m, 2H), 3.23-3.12(m, 2H), 2.47-2.30(m, 2H), 2.25-1.98(m, 3H), 1.79-1.66(m, 1H), 1.52-1.28(m, 3H),1.07-0.94(m, 9H);
비선광도: [α]D-13.8(c 1.00, 메탄올).
실시예 57(1)∼57(4)
실시예 56에서 제조한 화합물과 해당하는 알데히드 화합물을 이용하여 실시예 10과 동일한 조작을 하여 이하에 도시한 본 발명 화합물을 얻었다.
실시예 57(1)
(3S)-1-부틸-2,5-디옥소-3-((1S)-1-히드록시-2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.43(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.61-7.43(m, 5H), 4.32(s, 2H), 4.16(d, J=2.1Hz, 1H), 4.12-3.99(m, 1H), 3.90-3.72(m, 1H), 3.64-3.44(m, 3H), 3.30-3.12(m, 1H), 3.20(dd, J=9.3, 2.1Hz, 1H), 2.60-2.30(m, 9H), 2.24-2.10(m, 1H), 2.10-1.95(m, 1H), 1.78-1.60(m, 1H), 1.54-1.30(m, 3H), 1.00(d, J=6.6Hz, 3H), 0.98(d, J=6.6Hz, 3H), 0.96(t, J=6.9Hz, 3H).
실시예 57(2)
(3S)-1-부틸-2,5-디옥소-3-((1S)-1-히드록시-2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.51(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.52(d, J=8.7Hz, 2H), 7.43-7.36(m, 2H), 7.21-7.14(m, 1H), 7.10-7.00(m, 4H), 4.33(s, 2H), 4.14(d, J=2.1Hz, 1H), 4.06-3.92(m, 1H), 3.81-3.66(m, 1H), 3.58-3.40(m, 3H), 3.30-3.10(m, 1H), 3.19(dd, J=9.6, 2.1Hz, 1H), 2.53-2.37(m, 2H), 2.37-2.18(m, 1H), 2.18-2.08(m, 1H), 2.06-1.95(m, 1H), 1.78-1.60(m, 1H), 1.50-1.26(m, 3H), 0.99(d, J=6.6Hz, 3H), 0.97(d, J=6.6Hz, 3H), 0.95(t, J=7.2Hz, 3H).
실시예 57(3)
(3S)-1-부틸-2,5-디옥소-3-((1S)-1-히드록시-2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.43(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.06(d, J=2.1Hz, 1H), 6.98(dd, J=8.1, 2.1Hz, 1H), 6.92(d, J=8.1Hz, 1H), 4.26(s, 4H), 4.23(s, 2H), 4.13(d, J=2.4Hz, 1H), 4.02-3.87(m, 1H), 3.77-3.62(m, 1H), 3.57-3.35(m, 3H), 3.28-3.08(m, 1H), 3.19(dd, J=9.6, 2.4Hz, 1H), 2.51-2.35(m, 2H), 2.35-2.18(m, 1H), 2.17-2.05(m, 1H), 2.05-1.90(m, 1H), 1.80-1.58(m, 1H), 1.50-1.26(m, 3H), 0.98(d, J=6.6Hz, 3H), 0.97(d, J=6.6Hz, 3H), 0.95(t, J=7.2Hz, 3H).
실시예 57(4)
(3S)-1-부틸-2,5-디옥소-3-((1S)-1-히드록시-2-메틸프로필)-9-(4-(4-메틸설포닐아미노페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.35(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.53(d, J=8.7Hz, 2H), 7.29(d, J=9.0Hz, 2H), 7.10-7.00(m, 4H), 4.33(s, 2H), 4.14(d, J=2.1Hz, 1H), 4.06-3.92(m, 1H), 3.81-3.66(m, 1H), 3.58-3.40(m, 3H), 3.25-3.10(m, 1H), 3.19(dd, J=9.6, 2.1Hz, 1H), 2.95(s, 3H), 2.54-2.37(m, 2H), 2.37-2.22(m, 1H), 2.18-2.08(m, 1H), 2.08-1.92(m, 1H), 1.78-1.60(m, 1H), 1.50-1.28(m, 3H), 0.99(d, J=6.6Hz, 3H), 0.97(d, J=6.6Hz, 3H), 0.95(t, J=7.5Hz, 3H).
실시예 58
(3R)-1-부틸-2,5-디옥소-3-((1R)-1-히드록시-2-메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸·염산염
(2R*,3R*)-N-(t-부틸옥시카르보닐)-2-아미노-3-히드록시-4-메틸펜탄산 대신에 (2R,3R)-N-(t-부틸옥시카르보닐)-2-아미노-3-히드록시-4-메틸펜탄산을 이용하여 실시예 42→실시예 43과 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.08(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 4.15(d, J=2.0Hz, 1H), 3.96(dt, J=13.0, 4.0Hz, 1H), 3.71(dt, J=13.0, 4.0Hz, 1H), 3.57-3.47(m, 1H), 3.40-3.34(m, 2H), 3.23-3.12(m, 2H), 2.47-2.30(m, 2H), 2.25-1.98(m, 3H), 1.79-1.66(m, 1H), 1.52-1.28(m, 3H), 1.07-0.94(m, 9H);
비선광도: [α]D+13.9(c 1.00, 메탄올).
실시예 59(1)∼59(4)
실시예 58에서 제조한 화합물과 해당하는 알데히드 화합물을 이용하여 실시예 10과 동일한 조작을 하여 이하에 도시한 본 발명 화합물을 얻었다.
실시예 59(1)
(3R)-1-부틸-2,5-디옥소-3-((1R)-1-히드록시-2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.43(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.61-7.43(m, 5H), 4.32(s, 2H), 4.16(d, J=2.1Hz, 1H), 4.12-3.99(m, 1H), 3.90-3.72(m, 1H), 3.64-3.44(m, 3H), 3.30-3.12(m, 1H), 3.20(dd, J=9.3, 2.1Hz, 1H), 2.60-2.30(m, 9H), 2.24-2.10(m, 1H), 2.10-1.95(m, 1H), 1.78-1.60(m, 1H), 1.54-1.30(m, 3H), 1.00(d, J=6.6Hz, 3H), 0.98(d, J=6.6Hz, 3H), 0.96(t, J=6.9Hz, 3H).
실시예 59(2)
(3R)-1-부틸-2,5-디옥소-3-((1R)-1-히드록시-2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.51(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.52(d, J=8.7Hz, 2H), 7.43-7.36(m, 2H), 7.21-7.14(m, 1H), 7.10-7.00(m, 4H), 4.33(s, 2H), 4.14(d, J=2.1Hz, 1H), 4.06-3.92(m, 1H), 3.81-3.66(m, 1H), 3.58-3.40(m, 3H), 3.30-3.10(m, 1H), 3.19(dd, J=9.6, 2.1Hz, 1H), 2.53-2.37(m, 2H), 2.37-2.18(m, 1H), 2.18-2.08(m, 1H), 2.06-1.95(m, 1H), 1.78-1.60(m, 1H), 1.50-1.26(m, 3H), 0.99(d, J=6.6Hz, 3H), 0.97(d, J=6.6Hz, 3H), 0.95(t, J=7.2Hz, 3H).
실시예 59(3)
(3R)-1-부틸-2,5-디옥소-3-((1R)-1-히드록시-2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.43(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.06(d, J=2.1Hz, 1H), 6.98(dd, J=8.1, 2.1Hz, 1H), 6.92(d, J=8.1Hz, 1H), 4.26(s, 4H), 4.23(s, 2H), 4.13(d, J=2.4Hz, 1H), 4.02-3.87(m, 1H), 3.77-3.62(m, 1H), 3.57-3.35(m, 3H), 3.28-3.08(m, 1H), 3.19(dd, J=9.6, 2.4Hz, 1H), 2.51-2.35(m, 2H), 2.35-2.18(m, 1H), 2.17-2.05(m, 1H), 2.05-1.90(m, 1H), 1.80-1.58(m, 1H), 1.50-1.26(m, 3H), 0.98(d, J=6.6Hz, 3H), 0.97(d, J=6.6Hz, 3H), 0.95(t, J=7.2Hz, 3H).
실시예 59(4)
(3R)-1-부틸-2,5-디옥소-3-((1R)-1-히드록시-2-메틸프로필)-9-(4-(4-메틸설포닐아미노페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.35(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.53(d, J=8.7Hz, 2H), 7.29(d, J=9.0Hz, 2H), 7.10-7.00(m, 4H), 4.33(s, 2H), 4.14(d, J=2.1Hz, 1H), 4.06-3.92(m, 1H), 3.81-3.66(m, 1H), 3.58-3.40(m, 3H), 3.25-3.10(m, 1H), 3.19(dd, J=9.6, 2.1Hz, 1H), 2.95(s, 3H), 2.54-2.37(m, 2H), 2.37-2.22(m, 1H), 2.18-2.08(m, 1H), 2.08-1.92(m, 1H), 1.78-1.60(m, 1H), 1.50-1.28(m, 3H), 0.99(d, J=6.6Hz, 3H), 0.97(d, J=6.6Hz, 3H), 0.95(t, J=7.5Hz, 3H).
실시예 60
(3R)-1-부틸-2,5-디옥소-3-((1S)-1-히드록시-2-메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸·염산염
(2R*,3S*)-N-(t-부틸옥시카르보닐)-2-아미노-3-히드록시-3-시클로헥실프로판산의 대신해서, (2R, 3S)-N-(t-부틸옥시카르보닐)-2-아미노-3-히드록시-4-메틸펜탄산을 이용하여 실시예 53→실시예 54와 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.51(클로로포름:메탄올:초산=10:2:1);
NMR(CD3OD): δ 4.08(d, J=1.5Hz, 1H), 4.02(dt, J=12.6, 3.9Hz, 1H), 3.70-3.00(m, 6H), 2.50-2.10(m, 4H), 1.80-1.60(m, 2H), 1.55-1.35(m, 3H), 1.02(d, J=6.6Hz, 3H), 0.99(t, J=6.6Hz, 3H), 0.93(d, J=6.6Hz, 3H);
비선광도: [α]D+21.2(c 1.00, 메탄올).
실시예 61(1)∼61(3)
실시예 60에서 제조한 화합물과 해당하는 알데히드 화합물을 이용하여 실시예 10과 동일한 조작을 하여 이하에 도시한 본 발명 화합물을 얻었다.
실시예 61(1)
(3R)-1-부틸-2,5-디옥소-3-((1S)-1-히드록시-2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.44(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.64-7.46(m, 5H), 4.32(s, 2H), 4.19-4.06(m, 1H), 4.10(d, J=1.5Hz, 1H), 3.80-3.53(m, 4H), 3.51(dd, J=10.2, 1.5Hz, 1H), 3.40-3.20(m, 1H), 2.70-2.30(m, 9H), 2.23-2.10(m, 1H), 1.83-1.60(m, 2H), 1.53-1.30(m, 3H), 1.02(d, J=6.6Hz, 3H), 0.96(t, J=7.2Hz, 3H), 0.93(d, J=6.6Hz, 3H).
실시예 61(2)
(3R)-1-부틸-2,5-디옥소-3-((1S)-1-히드록시-2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.44(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.06(d, J=2.1Hz, 1H), 6.98(dd, J=8.1, 2.1Hz, 1H), 6.92(d, J=8.1Hz, 1H), 4.26(s, 4H), 4.23(s, 2H), 4.08(d, J=1.5Hz, 1H), 4.08-3.96(m, 1H), 3.72-3.35(m, 4H), 3.49(dd, J=10.2, 1.5Hz, 1H), 3.28-3.08(m, 1H), 2.55-2.35(m, 2H), 2.35-2.18(m, 1H), 2.18-2.08(m, 1H), 1.82-1.62(m, 2H), 1.52-1.25(m, 3H), 1.01(d, J=6.6Hz, 3H), 0.95(t, J=7.2Hz, 3H), 0.92(d, J=6.6Hz, 3H).
실시예 61(3)
(3R)-1-부틸-2,5-디옥소-3-((1S)-1-히드록시-2-메틸프로필)-9-(4-(4-메틸설포닐아미노페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.42(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.53(d, J=8.7Hz, 2H), 7.29(d, J=9.0Hz, 2H), 7.07(d, J=8.7Hz, 2H), 7.03(d, J=9.0Hz, 2H), 4.33(s, 2H), 4.13-4.00(m, 1H), 4.09(d, J=1.5Hz, 1H), 3.75-3.62(m, 1H), 3.62-3.39(m, 3H), 3.49(dd, J=10.5, 1.5Hz, 1H), 3.26-3.12(m, 1H), 2.95(s, 3H), 2.56-2.37(m, 2H), 2.37-2.20(m, 1H), 2.20-2.10(m, 1H), 1.82-1.63(m, 2H), 1.50-1.30(m, 3H), 1.01(d, J=6.6Hz, 3H), 0.95(t, J=7.2Hz, 3H), 0.92(d, J=6.6Hz, 3H).
실시예 62
(3S)-1-부틸-2,5-디옥소-3-((1R)-1-히드록시-2-메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸·염산염
(2R*,3S*)-N-(t-부틸옥시카르보닐)-2-아미노-3-히드록시-3-시클로헥실프로판산 대신에 (2S,3R)-N-(t-부틸옥시카르보닐)-2-아미노-3-히드록시-4-메틸펜탄산을 이용하여 실시예 53→실시예 54와 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.51(클로로포름:메탄올:초산=10:2:1);
NMR(CD3OD): δ 4.08(d, J=1.5Hz, 1H), 4.02(dt, J=12.6, 3.9Hz, 1H), 3.70-3.00(m, 6H), 2.50-2.10(m, 4H), 1.80-1.60(m, 2H), 1.55-1.35(m, 3H), 1.02(d, J=6.6Hz, 3H), 0.99(t, J=6.6Hz, 3H), 0.93(d, J=6.6Hz, 3H);
비선광도: [α]D-23.4(c 1.00, 메탄올).
실시예 63(1)∼63(3)
실시예 62에서 제조한 화합물과 해당하는 알데히드 화합물을 이용하여 실시예 10과 동일한 조작을 하여 이하에 도시한 본 발명 화합물을 얻었다.
실시예 63(1)
(3S)-1-부틸-2,5-디옥소-3-((1R)-1-히드록시-2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·2염산염
TLC: Rf 0.44(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.64-7.46(m, 5H), 4.32(s, 2H), 4.19-4.06(m, 1H), 4.10(d, J=1.5Hz, 1H), 3.80-3.53(m, 4H), 3.51(dd, J=10.2, 1.5Hz, 1H), 3.40-3.20(m, 1H), 2.70-2.30(m, 9H), 2.23-2.10(m, 1H), 1.83-1.60(m, 2H), 1.53-1.30(m, 3H), 1.02(d, J=6.6Hz, 3H), 0.96(t, J=7.2Hz, 3H), 0.93(d, J=6.6Hz, 3H).
실시예 63(2)
(3S)-1-부틸-2,5-디옥소-3-((1R)-1-히드록시-2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.44(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.06(d, J=2.1Hz, 1H), 6.98(dd, J=8.1, 2.1Hz, 1H), 6.92(d, J=8.1Hz, 1H), 4.26(s, 4H), 4.23(s, 2H), 4.08(d, J=1.5Hz, 1H), 4.08-3.96(m, 1H), 3.72-3.35(m, 4H), 3.49(dd, J=10.2, 1.5Hz, 1H), 3.28-3.08(m, 1H), 2.55-2.35(m, 2H), 2.35-2.18(m, 1H), 2.18-2.08(m, 1H), 1.82-1.62(m, 2H), 1.52-1.25(m, 3H), 1.01(d, J=6.6Hz, 3H), 0.95(t, J=7.2Hz, 3H), 0.92(d, J=6.6Hz, 3H).
실시예 63(3)
(3S)-1-부틸-2,5-디옥소-3-((1R)-1-히드록시-2-메틸프로필)-9-(4-(4-메틸설포닐아미노페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
TLC: Rf 0.42(클로로포름:메탄올=10:1);
NMR(CD3OD): δ 7.53(d, J=8.7Hz, 2H), 7.29(d, J=9.0Hz, 2H), 7.07(d, J=8.7Hz, 2H), 7.03(d, J=9.0Hz, 2H), 4.33(s, 2H), 4.13-4.00(m, 1H), 4.09(d, J=1.5Hz, 1H), 3.75-3.62(m, 1H), 3.62-3.39(m, 3H), 3.49(dd, J=10.5, 1.5Hz, 1H), 3.26-3.12(m, 1H), 2.95(s, 3H), 2.56-2.37(m, 2H), 2.37-2.20(m, 1H), 2.20-2.10(m, 1H), 1.82-1.63(m, 2H), 1.50-1.30(m, 3H), 1.01(d, J=6.6Hz, 3H), 0.95(t, J=7.2Hz, 3H), 0.92(d, J=6.6Hz, 3H).
실시예 64
(3S)-2,5-디옥소-3-(3-벤질옥시카르보닐아미노프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸·염산염
참고예 2에서 합성한 수지(3), N-(2-페닐에틸)-4-피페리돈, 2,4,6-트리메톡시벤질아민 및 Nα-(t-부틸옥시카르보닐)-Nδ-(벤질옥시카르보닐)-L-오르니틴을 이용하여 참고예9→참고예 10→실시예 1과 동일한 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.33(클로로포름:메탄올=10:1);
NMR(DMSO-d6):δ 10.80-10.00(m, 1H), 8.65-8.45(m, 1H), 8.33(s, 1H), 7.50-7.20(m, 10H), 5.01(s, 2H), 4.01(m, 1H), 3.70-3.45(m, 3H), 3.45-3.20(m, 3H), 3.15-2.90(m, 4H), 2.50-2.30(m, 2H), 2.10-1.90(m, 1H), 1.87-1.60(m, 3H), 1.60-1.35(m, 2H).
실시예 65
(3S)-1-메틸-2,5-디옥소-3-(3-벤질옥시카르보닐아미노프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸·초산염
참고예 2에서 합성한 수지(3), N-(2-페닐에틸)-4-피페리돈, 메틸아민 및 Nα-(t-부틸옥시카르보닐)-Nδ-(벤질옥시카르보닐)-L-오르니틴을 이용하여 실시예 19와 같은 조작을 하여 이하의 물성치를 갖는 본 발명 화합물을 얻었다.
TLC: Rf 0.36(클로로포름:메탄올=10:1);
MS(ESI, Pos., 40 V): 493(M+H)+;
HPLC 조건: F;
HPLC 유지 시간: 3.36분.
실시예 66
(3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-페닐옥시페닐메틸)-9-옥사이드-1,4,9-트리아자스피로[5.5]운데칸
실시예 40(90)에서 제조한 화합물(104 mg)의 아세톤(4 ml) 용액에 물(1 ml), 탄산수소나트륨(210 mg), 옥손(615 mg)(상품명)을 첨가하였다. 반응 혼합물을 실온에서 1시간 교반하였다. 반응 혼합물을 초산에틸로 희석하고, 포화탄산수소나트륨 수용액, 포화염화나트륨 수용액으로 세정하고, 무수 황산마그네슘으로 건조시켜 농축하였다. 잔류물을 분취용 박층 크로마토그래피(클로로포름:메탄올=30:1,20:1)에 의해 정제하여 이하의 물성치를 갖는 본 발명 화합물(73 mg)을 얻었다.
TLC: Rf 0.50(클로로포름:메탄올=9:1);
NMR(CDCl3): δ 7.49(dt, J=8.7, 2.1Hz, 2H), 7.36(ddt, J=8.7, 7.2, 2.1Hz, 2H), 7.14(tt, J=7.2, 1.2Hz, 1H), 7.04(dq, J=8.7, 1.2Hz, 2H), 7.01(dt, J=8.7, 2.1Hz, 2H), 5.82(brs, 1H), 4.32(s, 2H), 4.07-3.85(m, 3H), 3.55-3.46(m, 2H), 3.19-2.97(m, 4H), 2.02-1.49(m, 11H), 1.48-1.12(m, 6H), 1.08-0.90(m, 2H), 0.90(t, J=7.2Hz, 3H).
실시예 67(H32-1)∼67(H34-15)
참고예 2에서 제조한 수지(3), 해당하는 4-피페리돈 유도체, 해당하는 아민 유도체, 해당하는 아미노산 유도체 및 해당하는 알데히드 유도체를 이용하여 실시예 23과 동일한 조작을 하여 이하의 표 32A-1∼34A-2에 화합물명을 나타내고 표 32B-1∼34B-3에 구조식을 도시한 본 발명 화합물을 얻었다. 또한, 이들의 본 발명 화합물의 물성치를 이하의 표 32C-1∼34C-1에 나타내었다.
[표 32A-1]
실시예 번호
화합물명
67(H32-1)1-부틸-2,5-디옥소-3-벤질-9-(4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H32-2)1-부틸-2,5-디옥소-3-벤질-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H32-3)1-부틸-2,5-디옥소-3-벤질-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H32-4)1-부틸-2,5-디옥소-3-벤질-9-(4-벤질옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H32-5)1-부틸-2,5-디옥소-3-벤질-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H32-6)1-부틸-2,5-디옥소-3-벤질-9-(2-페닐이미다졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H32-7)1-(2-메톡시에틸)-2,5-디옥소-3-벤질-9-(4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H32-8)1-(2-메톡시에틸)-2,5-디옥소-3-벤질-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H32-9)1-(2-메톡시에틸)-2,5-디옥소-3-벤질-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 32A-2]
실시예 번호
화합물명
67(H32-10)1-(2-메톡시에틸)-2,5-디옥소-3-벤질-9-(4-벤질옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H32-11)1-(2-메톡시에틸)-2,5-디옥소-3-벤질-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H32-12)1-(2-메톡시에틸)-2,5-디옥소-3-벤질-9-(2-페닐이미다졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H32-13)1-벤질-2,5-디옥소-3-벤질-9-(4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H32-14)1-벤질-2,5-디옥소-3-벤질-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H32-15)1-벤질-2,5-디옥소-3-벤질-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H32-16)1-벤질-2,5-디옥소-3-벤질-9-(4-벤질옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H32-17)1-벤질-2,5-디옥소-3-벤질-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H32-18)1-벤질-2,5-디옥소-3-벤질-9-(2-페닐이미다졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 32A-3]
실시예 번호
화합물명
67(H32-19)(3S)-1-부틸-2,5-디옥소-3-(4-메톡시벤질)-9-시클로헥실메틸-1,4,9-트리아자스피로[5.5]운데칸
67(H32-20)(3S)-1-부틸-2,5-디옥소-3-(4-메톡시벤질)-9-(2-메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸
67(H32-21)(3R)-1-부틸-2,5-디옥소-3-(4-메톡시벤질)-9-시클로헥실메틸-1,4,9-트리아자스피로[5.5]운데칸
67(H32-22)(3R)-1-부틸-2,5-디옥소-3-(4-메톡시벤질)-9-(2-메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸
67(H32-23)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(4-클로로페닐)티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H32-24)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(4-메톡시페닐)티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 33A-1]
실시예 번호
화합물명
67(H33-1)1-(2-클로로페닐메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H33-2)1-(2-플루오로페닐메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H33-3)1-(2-트리플루오로메틸페닐메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H33-4)1-시클로프로필메틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H33-5)1-(2,2-디메틸프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H33-6)1-(티오펜-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H33-7)1-(푸란-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H33-8)1-((2E)-2-부테닐)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 33A-2]
실시예 번호
화합물명
67(H33-9)1-(2-메톡시에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(5-에틸티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H33-10)1-(2-페닐옥시에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H33-11)1-(티오펜-2-일메틸)-2,5-디옥소-3-시클로헥실메틸-9-(2-클로로-4-히드록시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H33-12)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-클로로-4-히드록시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H33-13)1-(티오펜-2-일메틸)-2,5-디옥소-3-시클로헥실메틸-9-(4-히드록시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H33-14)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-히드록시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H33-15)1-(티오펜-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(2-클로로-4-히드록시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H33-16)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-클로로-4-히드록시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 33A-3]
실시예 번호
화합물명
67(H33-17)1-(티오펜-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-히드록시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H33-18)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-히드록시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 34A-1]
실시예 번호
화합물명
67(H34-1)(3S)-1-부틸-2,5-디옥소-3-((1S)-1-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H34-2)(3S)-1-부틸-2,5-디옥소-3-((1S)-1-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H34-3)(3S)-1-(2-메톡시에틸)-2,5-디옥소-3-((1S)-1-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H34-4)(3S)-1-(2-메톡시에틸)-2,5-디옥소-3-((1S)-1-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H34-5)(3S)-1-부틸-2,5-디옥소-3-(시클로헥실메틸옥시메틸)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H34-6)(3S)-1-부틸-2,5-디옥소-3-(시클로헥실메틸옥시메틸)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H34-7)(3S)-1-(2-메톡시에틸)-2,5-디옥소-3-(시클로헥실메틸옥시메틸)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 34A-2]
실시예 번호
화합물명
67(H34-8)(3S)-1-(2-메톡시에틸)-2,5-디옥소-3-(시클로헥실메틸옥시메틸)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H34-9)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-클로로-1,3-벤조디옥솔란-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H34-10)1-(2-메톡시에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-클로로-1,3-벤조디옥솔란-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H34-11)1-(3-메틸-2-부테닐)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H34-12)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-((2E)-3-페닐-2-프로페닐)-1,4,9-트리아자스피로[5.5]운데칸
67(H34-13)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-((2E)-3-페닐-2-프로페닐)-1,4,9-트리아자스피로[5.5]운데칸
67(H34-14)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(퀴놀린-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
67(H34-15)1-(3-메틸-2-부테닐)-2,5-디옥소-3-시클로헥실메틸-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 32B-1]
[표 32B-2]
[표 32B-3]
[표 32B-4]
[표 33B-1]
[표 33B-2]
[표 33B-3]
[표 34B-1]
[표 34B-2]
[표 34B-3]
[표 32C-1]
[표 33C-1]
[표 34C-1]
실시예 68(H35-1)∼68(H35-61)
참고예 2에서 제조한 수지(3), 해당하는 4-피페리돈 유도체, 해당하는 아민 유도체, 해당하는 아미노산 유도체를 이용하여 참고예 11과 동일한 조작을 하고, 해당하는 알콜 유도체를 이용하여 참고예 12→실시예 33과 동일한 조작을 하며, 수지로부터 본 발명 화합물을 추출하여, 이하의 표 35A-1∼35A-8에 화합물명을 나타내고, 표 35B-1∼35B-13에 구조식을 도시한 본 발명 화합물을 얻었다. 또한, 이들의 본 발명 화합물의 물성치를 이하의 표 35C-1∼35C-3에 나타내었다.
[표 35A-1]
실시예 번호
화합물명
68(H35-1)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-클로로-4-(2-(N,N-디에틸아미노)에틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-2)1-(티오펜-2-일메틸)-2,5-디옥소-3-시클로헥실메틸-9-(4-(2-(N,N-디에틸아미노)에틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-3)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(2-(N,N-디에틸아미노)에틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-4)1-(티오펜-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(2-클로로-4-(2-(N,N-디에틸아미노)에틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-5)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-클로로-4-(2-(N,N-디에틸아미노)에틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-6)1-(티오펜-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-(2-(N,N-디에틸아미노)에틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-7)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(2-(N,N-디에틸아미노)에틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 35A-2]
실시예 번호
화합물명
68(H35-8)1-(티오펜-2-일메틸)-2,5-디옥소-3-시클로헥실메틸-9-(2-클로로-4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-9)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-클로로-4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-10)1-(티오펜-2-일메틸)-2,5-디옥소-3-시클로헥실메틸-9-(4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-11)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-12)1-(티오펜-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(2-클로로-4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-13)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-클로로-4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-14)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-15)1-(티오펜-2-일메틸)-2,5-디옥소-3-시클로헥실메틸-9-(2-클로로-4-에톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 35A-3]
실시예 번호
화합물명
68(H35-16)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-클로로-4-에톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-17)1-(티오펜-2-일메틸)-2,5-디옥소-3-시클로헥실메틸-9-(4-에톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-18)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-에톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-19)1-(티오펜-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(2-클로로-4-에톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-20)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-클로로-4-에톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-21)1-(티오펜-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-에톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-22)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-에톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-23)1-(티오펜-2-일메틸)-2,5-디옥소-3-시클로헥실메틸-9-(2-클로로-4-프로필옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 35A-4]
실시예 번호
화합물명
68(H35-24)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-클로로-4-프로필옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-25)1-(티오펜-2-일메틸)-2,5-디옥소-3-시클로헥실메틸-9-(4-프로필옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-26)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-프로필옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-27)1-(티오펜-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(2-클로로-4-프로필옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-28)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-클로로-4-프로필옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-29)1-(티오펜-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-프로필옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-30)1-(티오펜-2-일메틸)-2,5-디옥소-3-시클로헥실메틸-9-(2-클로로-4-이소프로필옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-31)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-클로로-4-이소프로필옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 35A-5]
실시예 번호
화합물명
68(H35-32)1-(티오펜-2-일메틸)-2,5-디옥소-3-시클로헥실메틸-9-(4-이소프로필옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-33)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-이소프로필옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-34)1-(티오펜-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(2-클로로-4-이소프로필옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-35)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-클로로-4-이소프로필옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-36)1-(티오펜-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-이소프로필옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-37)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-이소프로필옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-38)1-(티오펜-2-일메틸)-2,5-디옥소-3-시클로헥실메틸-9-(2-클로로-4-(시클로프로필메틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸표
[표 35A-6]
실시예 번호
화합물명
68(H35-39)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-클로로-4-(시클로프로필메틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-40)1-(티오펜-2-일메틸)-2,5-디옥소-3-시클로헥실메틸-9-(4-(시클로프로필메틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-41)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(시클로프로필메틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-42)1-(티오펜-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(2-클로로-4-(시클로프로필메틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-43)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-클로로-4-(시클로프로필메틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-44)1-(티오펜-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-(시클로프로필메틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-45)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(시클로프로필메틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 35A-7]
실시예 번호
화합물명
68(H35-46)1-(티오펜-2-일메틸)-2,5-디옥소-3-시클로헥실메틸-9-(2-클로로-4-시클로부틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-47)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-클로로-4-시클로부틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-48)1-(티오펜-2-일메틸)-2,5-디옥소-3-시클로헥실메틸-9-(4-시클로부틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-49)1-(티오펜-2-일메틸)-2,5-디옥소-3-시클로헥실메틸-9-(2-클로로-4-시클로펜틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-50)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-클로로-4-시클로펜틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-51)1-(티오펜-2-일메틸)-2,5-디옥소-3-시클로헥실메틸-9-(4-시클로펜틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-52)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-시클로펜틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-53)1-(티오펜-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(2-클로로-4-시클로펜틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 35A-8]
실시예 번호
화합물명
68(H35-54)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-클로로-4-시클로펜틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-55)1-(티오펜-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-시클로펜틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-56)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-시클로펜틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-57)1-(티오펜-2-일메틸)-2,5-디옥소-3-시클로헥실메틸-9-(2-클로로-4-(테트라히드로피란-4-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-58)1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-클로로-4-(테트라히드로피란-4-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-59)1-(티오펜-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(2-클로로-4-(테트라히드로피란-4-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-60)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-시클로부틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
68(H35-61)1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(테트라히드로피란-4-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 35B-1]
[표 35B-2]
[표 35B-3]
[표 35B-4]
[표 35B-5]
[표 35B-6]
[표 35B-7]
[표 35B-8]
[표 35B-9]
[표 35B-10]
[표 35B-11]
[표 35B-12]
[표 35B-13]
[표 35C-1]
[표 35C-2]
[표 35C-3]
실시예 69(H36-1)∼69(H36-24)
실시예 14에서 제조한 화합물 대신에 해당하는 아민 유도체와 해당하는 산클로라이드 유도체를 이용하여 실시예 22와 동일한 조작을 하여 이하의 표 36A-1∼36A-4에 화합물명을 나타내고, 표 36B-1∼36B-5에 구조식을 나타낸 본 발명 화합물을 얻었다. 또한, 이들의 본 발명 화합물의 물성치를 이하의 표 36C-1에 나타내었다.
[표 36A-1]
실시예 번호
화합물명
69(H36-1)(3S)-1-프로필-2,5-디옥소-3-((2-페닐페닐)카르보닐아미노메틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
69(H36-2)(3S)-1-프로필-2,5-디옥소-3-((3-페닐페닐)카르보닐아미노메틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
69(H36-3)(3S)-1-프로필-2,5-디옥소-3-((4-페닐페닐)카르보닐아미노메틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
69(H36-4)(3S)-1-프로필-2,5-디옥소-3-((2-페닐페닐)아세틸아미노메틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
69(H36-5)(3S)-1-프로필-2,5-디옥소-3-((3-페닐페닐)아세틸아미노메틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸,
69(H36-6)(3S)-1-프로필-2,5-디옥소-3-((4-페닐페닐)아세틸아미노메틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
69(H36-7)(3S)-1-프로필-2,5-디옥소-3-(2-(2-페닐페닐)카르보닐아미노에틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 36A-2]
실시예 번호
화합물명
69(H36-8)(3S)-1-프로필-2,5-디옥소-3-(2-(3-페닐페닐)카르보닐아미노에틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
69(H36-9)(3S)-1-프로필-2,5-디옥소-3-(2-(4-페닐페닐)카르보닐아미노에틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
69(H36-10)(3S)-1-프로필-2,5-디옥소-3-(2-(2-페닐페닐)아세틸아미노에틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
69(H36-11)(3S)-1-프로필-2,5-디옥소-3-(2-(3-페닐페닐)아세틸아미노에틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
69(H36-12)(3S)-1-프로필-2,5-디옥소-3-(2-(4-페닐페닐)아세틸아미노에틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
69(H36-13)(3S)-1-프로필-2,5-디옥소-3-(3-(2-페닐페닐)카르보닐아미노프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
69(H36-14)(3S)-1-프로필-2,5-디옥소-3-(3-(3-페닐페닐)카르보닐아미노프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 36A-3]
실시예 번호
화합물명
69(H36-I5)(3S)-1-프로필-2,5-디옥소-3-(3-(4-페닐페닐)카르보닐아미노프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
69(H36-16)(3S)-1-프로필-2,5-디옥소-3-(3-(2-페닐페닐)아세틸아미노프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
69(H36-17)(3S)-1-프로필-2,5-디옥소-3-(3-(3-페닐페닐)아세틸아미노프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
69(H36-18)(3S)-1-프로필-2,5-디옥소-3-(3-(4-페닐페닐)아세틸아미노프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
69(H36-19)(3S)-1-프로필-2,5-디옥소-3-(4-(2-페닐페닐)카르보닐아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
69(H36-20)(3S)-1-프로필-2,5-디옥소-3-(4-(3-페닐페닐)카르보닐아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
69(H36-21)(3S)-1-프로필-2,5-디옥소-3-(4-(4-페닐페닐)카르보닐아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 36A-4]
실시예 번호화합물명
69(H36-22)(3S)-1-프로필-2,5-디옥소-3-(4-(2-페닐페닐)아세틸아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
69(H36-23)(3S)-1-프로필-2,5-디옥소-3-(4-(3-페닐페닐)아세틸아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
69(H36-24)(3S)-1-프로필-2,5-디옥소-3-(4-(4-페닐페닐)아세틸아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸
[표 36B-1]
[표 36B-2]
[표 36B-3]
[표 36B-4]
[표 36B-5]
[표 36C-1]
[제제예]
제제예 1
이하의 각 성분을 통상적인 방법에 의해 혼합한 후, 타정하여 1정 속에 50 mg의 활성 성분을 함유하는 정제 100정을 얻었다.
·9-((3,5-디메틸-1-페닐)-4-피라졸릴)메틸)-2,5-디옥소-3-(2-메틸-1-프로필)-1-프로필-1,4,9-트리아자스피로[5.5]운데칸·2염산염
‥‥‥ 5.0 g
·카르복시메틸셀룰로오스칼슘(붕괴제)‥‥‥ 0.2 g
·스테아린산마그네슘(윤활제)‥‥‥ 0.1 g
·미결정 셀룰로오스 ‥‥‥ 4.7 g
제제예 2
이하의 각 성분을 통상적인 방법에 의해 혼합한 후, 용액을 통상적인 방법에 의해 멸균하여 5 ml씩 앰플에 충전하고, 통상적인 방법에 의해 동결 건조시켜 1앰플 속에 20 mg의 활성 성분을 함유하는 앰플 100개를 얻었다.
·9-((3,5-디메틸-1-페닐)-4-피라졸릴)메틸)-2,5-디옥소-3-(2-메틸-1-프로필)-1-프로필-1,4,9-트리아자스피로[5.5]운데칸·2염산염
‥‥‥ 2.0 g
·만니톨‥‥‥ 20 g
·증류수‥‥‥ 500 ml
[의약품에의 적용]
인간을 포함한 동물, 특히 인간에게 있어서 화학식 I로 표시되는 본 발명 화합물은 케모카인/케모카인 수용체의 작용을 제어하기 때문에, 각종 염증성 질환, 천식, 아토피성 피부염, 두드러기, 알레르기 질환(알레르기성 기관지 폐 아스페르길루스증, 알레르기성 호산구성 위장증 등), 신장염, 신장증, 간염, 관절염, 만성관절 류머티스, 건선, 비염, 결막염, 허혈 재관류 상해의 억제, 다발성 경화증, 궤양성 대장염, 급성 호흡 궁박 증후군, 세균 감염에 따른 쇼크, 당뇨병, 자기 면역 질환의 치료, 이식 장기 거부 반응, 면역 억제, 암전이 예방, 후천성 면역 부전 증후군의 예방 및/또는 치료에 유용하다.
화학식 I로 표시되는 본 발명 화합물, 그 비독성의 염, 산부가염, 또는 그 수화물을 상기한 목적으로 이용하기 위해서는 통상 전신적 또는 국소적으로, 경구 또는 비경구의 형태로 투여한다.
투여량은 연령, 체중, 증상, 치료 효과, 투여 방법, 처리 시간 등에 따라 다르지만, 통상, 성인 1인당, 1회에 대해 1 mg 내지 1000 mg 범위로, 1일 1회 내지 수회 경구 투여되거나 또는 성인 1인당, 1회에 대해 1 mg 내지 100 mg 범위에서, 1일 1회로 수회 비경구 투여(바람직하게는, 정맥내 투여)되거나 또는 1일 1시간 내지 24시간의 범위에서 정맥내에 지속적으로 투여한다.
물론 상기한 바와 같이, 투여량은 여러 가지 조건에 따라 변동하기 때문에, 상기 투여량보다 적은 양으로 충분한 경우도 있고, 또한 범위를 초과하여 필요한 경우도 있다.
본 발명 화합물을 투여할 때에는, 경구 투여를 위한 내복용 고형제, 내복용 액제 및 비경구 투여를 위한 주사제, 외용제, 좌제 등으로서 이용된다.
경구 투여를 위한 내복용 고형제에는 정제, 환제, 캡슐제, 산제, 과립제 등이 포함된다. 캡슐제에는 경질 캡슐 및 연질 캡슐이 포함된다.
이러한 내복용 고형제에 있어서, 하나 또는 그 이상의 활성 물질은 그 대로 또는 부형제(락토오스, 만니톨, 글루코오스, 미결정 셀룰로오스, 전분 등),결합제(히드록시프로필셀룰로오스, 폴리비닐피롤리돈, 메타규산알루민산마그네슘 등), 붕괴제(섬유소 글리콜산칼슘 등), 윤활제(스테아린산마그네슘 등), 안정제, 용해 보조제(글루타민산, 아스파라긴산 등) 등과 혼합되며, 통상적인 방법에 의해 제제화하여 이용된다. 또한, 필요에 따라 코팅제(백당, 젤라틴, 히드록시프로필셀룰로오스, 히드록시프로필메틸셀룰로오스프탈레이트 등)로 피복되어도 좋고, 또한 2이상의 층으로 피복되어도 좋다. 또한 젤라틴과 같은 흡수될 수 있는 물질의 캡슐도 포함된다.
경구 투여를 위한 내복용 액제는 약제적으로 허용되는 수제, 현탁제, 유제, 시럽제, 엘릭시르제 등을 포함한다. 이러한 액제에 있어서는, 하나 또는 그 이상의 활성 물질이 일반적으로 이용되는 희석제(정제수, 에탄올 또는 이들의 혼액 등)에 용해, 현탁 또는 유화된다. 또한 이 액제는 습윤제, 현탁화제, 유화제, 감미제, 풍미제, 방향제, 보존제, 완충제 등을 함유하고 있어도 좋다.
비경구 투여를 위한 주사제로서는, 용액, 현탁액, 유탁액 및 사용시 용제에 용해 또는 현탁하여 이용하는 고형의 주사제를 포함한다. 주사제는 하나 또는 그 이상의 활성 물질을 용제에 용해, 현탁 또는 유화시켜 이용된다. 용제로서, 예컨대 주사용 증류수, 생리식염수, 식물유, 프로필렌글리콜, 폴리에틸렌글리콜, 에탄올과 같은 알콜류 등 및 이들의 조합이 이용된다. 또한 이 주사제는 안정제, 용해 보조제(글루타민산, 아스파라긴산, 폴리솔베이트 80(등록 상표) 등), 현탁화제, 유화제, 무통화제, 완충제, 보존제 등을 포함하고 있어도 좋다. 이들은 최종 공정에서 멸균하거나 무균 조작법에 의해 제조, 조제된다. 또한 무균의 고형제, 예컨대 동결건조품을 제조하고, 그 사용전에 무균화 또는 무균의 주사용 증류수 또는 다른 용제에 용해하여 사용할 수도 있다.
비경구 투여를 위한 그 밖의 제제로서는, 하나 또는 그 이상의 활성 물질을 포함하며, 통상적인 방법에 의해 처방되는 외용액제, 연고제, 도포제, 흡입제, 분무제, 좌제 및 질내 투여를 위한 페서리 등이 포함된다.
분무제는 일반적으로 이용되는 희석제 이외에 아황산수소나트륨과 같은 안정제와 등장성을 부여하는 완충제, 예컨대 염화나트륨, 시트르산나트륨 혹은 시트르산과 같은 등장제를 함유하고 있어도 좋다. 분무제의 제조 방법은 예컨대 미국 특허 제2,868,691호 및 동 제3,095,355호에 상세히 기재되어 있다.
Claims (9)
- 하기 화학식 I로 표시되는 트리아자스피로[5. 5]운데칸 유도체, 이들의 4급 암모늄염, 이들의 N-옥사이드 또는 이들의 비독성염,화학식 I상기 식에서 R1은(1) 수소 원자,(2) C1∼18 알킬기,(3) C2∼18 알케닐기,(4) C2∼18 알키닐기,(5) -COR6,(6) -CONR7R8,(7) -COOR9,(8) -SO2R10,(9) -COCOOR11,(10) -CONR12COR13,(11) Cyc1, 또는(12) 임의로 선택된 1∼5개의 (a) 할로겐 원자, (b) -CONR7R8, (c) -COOR9, (d) -OR14, (e) -SR15, (f) -NR16R17, (g) -NR18COR19, (h) -SO2NR20R21, (i) -OCOR22, (j) -NR23SO2R24, (k) -NR25COOR26, (l) -NR27CONR28R29, (m) Cyc1, (n) 케토기, (o) -N(SO2R24)2에 의해 치환된 C1∼18 알킬기, C2∼18 알케닐기, 또는 C2∼18 알키닐기를 나타내고,(기 중, R6∼R9, R11∼R21, R23, R25및 R27∼R29는 각각 독립적으로(1) 수소 원자,(2) C1∼8 알킬기,(3) C2∼8 알케닐기,(4) C2∼8 알키닐기,(5) Cyc1, 또는(6) 임의로 선택된 1∼5개의 (a) Cyc1, (b) 할로겐 원자, (c) -OR30, (d) -SR31, (e) -NR32R33, (f) -COOR34, (g) -CONR35R36, (h) -NR37COR38, (i) -NR39SO2R40, (j) -N(SO2R40)2에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, 또는 C2∼8 알키닐기를 나타내거나,R7과 R8, R20과 R21, R28과 R29는 함께 1) C2∼6 알킬렌기, 2) -(C2∼6 알킬렌기)-O-(C2∼6 알킬렌기)-, 3) -(C2∼6 알킬렌기)-S-(C2∼6 알킬렌기)-, 또는 4) -(C2∼6 알킬렌기)-NR195-(C2∼6 알킬렌기)-를 나타내고(기 중, R195는 수소 원자, C1∼8 알킬기, 페닐기, 또는 페닐기에 의해 치환된 C1∼8 알킬기를 나타냄),R10, R22, R24및 R26은 각각 독립적으로(1) C1∼8 알킬기,(2) C2∼8 알케닐기,(3) C2∼8 알키닐기,(4) Cyc1, 또는(5) 임의로 선택된 1∼5개의 (a) Cyc1, (b) 할로겐 원자, (c) -OR30, (d) -SR31, (e) -NR32R33, (f) -COOR34, (g) -CONR35R36, (h) -NR37COR38, (i) -NR39SO2R40, (j) -N(SO2R40)2에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, 또는 C2∼8 알키닐기를 나타내며,(기 중, R30∼R37및 R39는 각각 독립적으로 수소 원자, C1∼8 알킬기, Cyc1, 또는 Cyc1에 의해 치환된 C1∼8 알킬기를 나타내거나,R35와 R36은 함께 1) C2∼6 알킬렌기, 2) -(C2∼6 알킬렌기)-O-(C2∼6 알킬렌기)-, 3) -(C2∼6 알킬렌기)-S-(C2∼6 알킬렌기)-, 또는 4) -(C2∼6 알킬렌기)-NR196-(C2∼6 알킬렌기)-를 나타내고(기 중, R196은 수소 원자, C1∼8 알킬기, 페닐기, 또는 페닐기에 의해 치환된 C1∼8 알킬기를 나타냄),R38및 R40은 각각 독립적으로 C1∼8 알킬기, Cyc1, 또는 Cyc1에 의해 치환된 C1∼8 알킬기를 나타냄)Cyc1은 C3∼15의 단고리, 이고리, 또는 삼고리식(축합 또는 스피로) 탄소고리, 또는 1∼4개의 질소 원자, 1∼3개의 산소 원자 및/또는 1∼3개의 유황 원자를 포함하는 3∼15원의 단고리, 이고리, 또는 삼고리식(축합 또는 스피로) 복소고리를 나타낸다.단, Cyc1은 1∼5개의 R51에 의해 치환되어도 좋고,R51은(1) C1∼8 알킬기,(2) C2∼8 알케닐기,(3) C2∼8 알키닐기,(4) 할로겐 원자,(5) 니트로기,(6) 트리플루오로메틸기(7) 트리플루오로메톡시기,(8) 니트릴기,(9) 케토기,(10) Cyc2(11) -OR52,(12) -SR53,(13) -NR54R55,(14) -COOR56,(15) -CONR57R58,(16) -NR59COR60,(17) -SO2NR61R62,(18) -OCOR63,(19) -NR64SO2R65,(20) -NR66COOR67,(21) -NR68CONR69R70,(22) -B(OR71)2,(23) -SO2R72,(24) -N(SO2R72)2, 또는(25) 임의로 선택된 1∼5개의 (a) 할로겐 원자, (b) Cyc2, (c) -OR52, (d) -SR53, (e) -NR54R55, (f) -COOR56, (g) -CONR57R58, (h) -NR59COR60, (i) -SO2NR61R62, (j) -OCOR63, (k) -NR64SO2R65, (l) -NR66COOR67, (m) -NR68CONR69R70, (n) -B(OR71)2, (o) -SO2R72, (p) -N(SO2R72)2에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기를 나타냄)(기 중, R52∼R62, R64, R66및 R68∼R71은 각각 독립적으로1) 수소 원자, 2) C1∼8 알킬기, 3) C2∼8 알케닐기, 4) C2∼8 알키닐기, 5) Cyc2, 또는 6) Cyc2, -OR73, -COOR74, -NR75R76에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기를 나타내거나,R57과 R58, R61과 R62, R69와 R70은 함께 1) C2∼6 알킬렌기, 2) -(C2∼6 알킬렌기)-O-(C2∼6 알킬렌기)-, 3) -(C2∼6 알킬렌기)-S-(C2∼6 알킬렌기)-, 또는 4) -(C2∼6 알킬렌기)-NR197-(C2∼6 알킬렌기)-를 나타내고(기 중, R197은 수소 원자, C1∼8 알킬기, 페닐기, 또는 페닐기에 의해 치환된 C1∼8 알킬기를 나타냄),R63, R65, R67및 R72는 각각 독립적으로 1) C1∼8 알킬기, 2) C2∼8 알케닐기, 3) C2∼8 알키닐기, 4) Cyc2, 또는 5) Cyc2, -OR73, -COOR74, -NR75R76에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기를 나타내며,(기 중, R73∼R76은 각각 독립적으로 수소 원자, C1∼8 알킬기, Cyc2, 또는 Cyc2에 의해 치환된 C1∼8 알킬기를 나타냄)Cyc2는 Cyc1과 동일한 의미를 나타낸다.단, Cyc2는 1∼5개의 R77에 의해 치환되어도 좋고,R77은1) C1∼8 알킬기,2) 할로겐 원자,3) 니트로기,4) 트리플루오로메틸기,5) 트리플루오로메톡시기,6) 니트릴기,7) -OR78,8) -NR79R80,9) -COOR81,10) -SR82,11) -CONR83R84,12) C2∼8 알케닐기,13) C2∼8 알키닐기,14) 케토기,15) Cyc6,16) -NR161COR162,17) -SO2NR163R164,18) -OCOR165,19) -NR166SO2R167,20) -NR168COOR169,21) -NR170CONR171R172,22) -SO2R173,23) -N(SO2R167)2,24) 임의로 선택된 1∼5개의 (a) 할로겐 원자, (b) -OR78, (c) -NR79R80, (d) -COOR81, (e) -SR82, (f) -CONR83R84, (g) 케토기, (h) Cyc6, (i) -NR161COR162, (j) -SO2NR163R164, (k) -OCOR165, (l) -NR166SO2R167, (m) -NR168COOR169, (n) -NR170CONR171R172, (o) -SO2R173, (p) -N(SO2R167)2에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기를 나타냄)(기 중, R78∼R84, R161∼R164, R166, R168및 R170∼R172는 각각 독립적으로 (a) 수소 원자, (b) C1∼8 알킬기, (c) C2∼8 알케닐기, (d) C2∼8 알키닐기, (e) Cyc6, (f) Cyc6, -OR174, -COOR175, -NR176R177, -CONR178R179에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기를 나타내거나,R83과 R84, R163과 R164, R171과 R172는 함께 1) C2∼6 알킬렌기, 2) -(C2∼6 알킬렌기)-O-(C2∼6 알킬렌기)-, 3) -(C2∼6 알킬렌기)-S-(C2∼6 알킬렌기)-, 또는 4) -(C2∼6 알킬렌기)-NR198-(C2∼6 알킬렌기)-를 나타내고(기 중, R198은 수소 원자, C1∼8 알킬기, 페닐기, 또는 페닐기에 의해 치환된 C1∼8 알킬기를 나타냄),R165, R167, R169및 R173은 각각 독립적으로 (a) C1∼8 알킬기, (b) C2∼8 알케닐기, (c) C2∼8 알키닐기, (d) Cyc6, 또는 (e) Cyc6, -OR174, -COOR175, -NR176R177, -CONR178R179에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기를 나타냄)(기 중, R174∼R177은 각각 독립적으로 1) 수소 원자, 2) C1∼8 알킬기, 3) Cyc6, 또는 4) Cyc6에 의해 치환된 C1∼8 알킬기를 나타내거나,R178과 R179는 함께 1) C2∼6 알킬렌기, 2) -(C2∼6 알킬렌기)-O-(C2∼6 알킬렌기)-, 3) -(C2∼6 알킬렌기)-S-(C2∼6 알킬렌기)-, 또는 4) -(C2∼6 알킬렌기)-NR199-(C2∼6 알킬렌기)-를 나타내고(기 중, R199는 수소 원자, C1∼8 알킬기, 페닐기, 또는 페닐기에 의해 치환된 C1∼8 알킬기를 나타냄),Cyc6은 C3∼8의 단고리식 탄소고리 또는 1∼4개의 질소 원자, 1∼2개의 산소 원자 및/또는 1∼2개의 유황 원자를 포함하는 3∼8원의 단고리식 복소고리를 나타낸다.단, Cyc6은 1∼5개의 R180에 의해 치환되어도 좋고,R180은(1) C1∼8 알킬기,(2) 할로겐 원자,(3) 니트로기,(4) 트리플루오로메틸기,(5) 트리플루오로메톡시기,(6) 니트릴기,(7) -OR181,(8) -NR182R183,(9) -COOR184,(10) -SR185, 또는(11) -CONR186R187을 나타내고(기 중, R181∼R187은 각각 독립적으로 1) 수소 원자, 2) C1∼8 알킬기, 3) 페닐기, 또는 4) 페닐기에 의해 치환된 C1∼8 알킬기를 나타내거나,R182와 R183, R186과 R187은 함께 1) C2∼6 알킬렌기, 2) -(C2∼6 알킬렌기)-O-(C2∼6 알킬렌기)-, 3) -(C2∼6 알킬렌기)-S-(C2∼6 알킬렌기)-, 또는 4) - (C2∼6 알킬렌기)-NR200-(C2∼6 알킬렌기)-를 나타냄(기 중, R200은 수소 원자, C1∼8 알킬기, 페닐기, 페닐기에 의해 치환된 C1∼8 알킬기를 나타냄)),R2는(1) 수소 원자,(2) C1∼8 알킬기,(3) C2∼8 알케닐기,(4) C2∼8 알키닐기,(5) -OR90,(6) Cyc3, 또는(7) 임의로 선택된 1∼5개의 (a) 할로겐 원자, (b) -OR90, (c) -SR91, (d) -NR92R93, (e) -COOR94, (f) -CONR95R96, (g) -NR97COR98, (h) -SO2NR99R100, (i) -OCOR101, (j) -NR102SO2R103, (k) -NR104COOR105, (l) -NR106CONR107R108, (m) Cyc3, (n) 케토기, (o) -N(SO2R103)2에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기 또는 C2∼8 알키닐기를 나타내고,(기 중, R90∼R100, R102, R104및 R106∼R108은 각각 독립적으로 1) 수소 원자, 2) C1∼8 알킬기, 3) C2∼8 알케닐기, 4) C2∼8 알키닐기, 5) Cyc3, 또는 6) Cyc3에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기를 나타내거나,R95와 R96, R99와 R100, R107과 R108은 함께 1) C2∼6 알킬렌기, 2) -(C2∼6 알킬렌기)-O-(C2∼6 알킬렌기)-, 3) -(C2∼6 알킬렌기)-S-(C2∼6 알킬렌기)-, 또는 4)-(C2∼6 알킬렌기)-NR201-(C2∼6 알킬렌기)-를 나타내고(기 중, R201은 수소 원자, C1∼8 알킬기, 페닐기, 또는 페닐기에 의해 치환된 C1∼8 알킬기를 나타냄),R101, R103및 R105는 각각 독립적으로 1) C1∼8 알킬기, 2) C2∼8 알케닐기, 3) C2∼8 알키닐기, 또는 4) Cyc3 또는 Cyc3에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기를 나타내며,Cyc3은 Cyc1과 동일한 의미를 나타낸다.단, Cyc3은 1∼5개의 R109에 의해 치환되어도 좋고,R109는 R51과 동일한 의미를 나타냄)R3및 R4는 각각 독립적으로(1) 수소 원자,(2) C1∼8 알킬기,(3) C2∼8 알케닐기,(4) C2∼8 알키닐기,(5) -COOR120,(6) -CONR121R122,(7) Cyc4, 또는(8) 임의로 선택된 1∼5개의 (a) 할로겐 원자, (b) 니트릴기, (c) Cyc4, (d)-COOR120, (e) -CONR121R122, (f) -OR123, (g) -SR124, (h) -NR125R126, (i) -NR127COR128, (j) -SO2NR129R130, (k) -OCOR131, (l) -NR132SO2R133, (m) -NR134COOR135, (n) -NR136CONR137R138, (o) -S-SR139, (p) -NHC(=NH)NHR140, (q) 케토기, (r) -NR145CONR146COR147, (s) -N(SO2R133)2에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, 또는 C2∼8 알키닐기를 나타내고,(기 중, R120∼R130, R132, R134, R136∼R138, R145및 R146은 각각 독립적으로 1) 수소 원자, 2) C1∼8 알킬기, 3) C2∼8 알케닐기, 4) C2∼8 알키닐기, 5) Cyc4, 또는 6) Cyc4, 할로겐 원자, -OR148, -SR149, -COOR150, 또는 -NHCOR141에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기를 나타내거나,R121과 R122, R129와 R130, R137과 R138은 함께 1) C2∼6 알킬렌기, 2) -(C2∼6 알킬렌기)-O-(C2∼6 알킬렌기)-, 3) -(C2∼6 알킬렌기)-S-(C2∼6 알킬렌기)-, 또는 4) -(C2∼6 알킬렌기)-NR202-(C2∼6 알킬렌기)-를 나타내고(기 중, R202는 수소 원자, C1∼8 알킬기, 페닐기, 페닐기에 의해 치환된 C1∼8 알킬기를 나타냄),R131, R133, R135, R139및 R147은 각각 독립적으로 1) C1∼8 알킬기, 2) C2∼8 알케닐기, 3) C2∼8 알키닐기, 4) Cyc4, 또는 5) Cyc4, 할로겐 원자, -OR148, -SR149, -COOR150, 또는 -NHCOR141에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기를 나타내고,R140은 수소 원자, -COOR142, 또는 -SO2R143을 나타내고,(기 중, R141∼R143은 각각 독립적으로 1) C1∼8 알킬기, 2) C2∼8 알케닐기, 3) C2∼8 알키닐기, 4) Cyc4, 또는 5) Cyc4에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기를 나타내며,R148∼R150은 각각 독립적으로 1) 수소 원자, 2) C1∼8 알킬기, 3) C2∼8 알케닐기, 4) C2∼8 알키닐기, 5) Cyc4, 또는 6) Cyc4에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, C2∼8 알키닐기를 나타내고,Cyc4는 Cyc1과 동일한 의미를 나타낸다.단, Cyc4는 1∼5개의 R144에 의해 치환되어도 좋고, R144는 R51과 동일한 의미를 나타냄)를 나타내거나R3과 R4는 함께(기 중, R190및 R191은 각각 독립적으로 R3또는 R4와 동일한 의미를 나타냄)를 나타내고,R5는(1) 수소 원자,(2) C1∼8 알킬기,(3) Cyc5, 또는(4) Cyc5에 의해 치환된 C1∼8 알킬기를 나타낸다.(기 중, Cyc5는 Cyc1과 동일한 의미를 나타낸다.단, Cyc5는 1∼5개의 R160에 의해 치환되어도 좋고, R160은 R51과 동일한 의미를 나타낸다.)
- 제1항에 있어서, 제1항에 기재한 화학식 I 중, R3및 R4가 수소 원자인 화합물.
- 제1항에 있어서, 제1항에 기재한 화학식 I 중, R3이 수소 원자,R4가(1) C1∼8 알킬기,(2) C2∼8 알케닐기,(3) C2∼8 알키닐기,(4) -COOR120,(5) -CONR121R122,(6) Cyc4, 또는(7) 임의로 선택된 1∼5개의 (a) 할로겐 원자, (b) 니트릴기, (c) Cyc4, (d) -COOR120, (e) -CONR121R122, (f) -OR123, (g) -SR124, (h) -NR125R126, (i) -NR127COR128, (j) -SO2NR129R130, (k) -OCOR131, (l) -NR132SO2R133, (m) -NR134COOR135, (n) -NR136CONR137R138, (o) -S-SR139, (p) -NHC(=NH)NHR140, (q) 케토기, (r) -NR145CONR146COR147, (s) -N(SO2R133)2에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, 또는 C2∼8 알키닐기인 화합물.(모든 기호는 제1항 기재와 동일한 의미를 나타낸다.)
- 제1항에 있어서, 제1항에 기재한 화학식 I 중, R3및 R4가 각각 독립적으로,(1) C1∼8 알킬기,(2) C2∼8 알케닐기,(3) C2∼8 알키닐기,(4) -COOR120,(5) -CONR121R122,(6) Cyc4, 또는(7) 임의로 선택된 1∼5개의 (a) 할로겐 원자, (b) 니트릴기, (c) Cyc4, (d) -COOR120, (e) -CONR121R122, (f) -OR123, (g) -SR124, (h) -NR125R1126, (i) -NR127COR128, (j) -SO2NR129R130, (k) -OCOR131, (l) -NR132SO2R133, (m) -NR134COOR135, (n) -NR136CONR137R138, (o) -S-SR139, (p) -NHC(=NH)NHR140, (q) 케토기, (r) -NR145CONR146COR147, (s) -N(SO2R133)2에 의해 치환된 C1∼8 알킬기, C2∼8 알케닐기, 또는 C2∼8 알키닐기인 화합물.(모든 기호는 제1항 기재와 동일한 의미를 나타낸다.)
- 제1항에 있어서, 제1항에 기재한 화학식 I 중, R3과 R4가 함께기인 화합물.(기 중, 모든 기호는 제1항 기재와 동일한 의미를 나타낸다.)
- 제1항에 있어서, 화합물이(1) 9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-2,5-디옥소-3-(2-메틸-1-프로필)-1-프로필-1,4,9-트리아자스피로[5.5]운데칸,(2) 9-(1,4-벤조디옥산-6-일메틸)-1-부틸-3-시클로헥실메틸-2,5-디옥소-1,4,9-트리아자스피로[5.5]운데칸,(3) 1-부틸-3-시클로헥실메틸-2,5-디옥소-9-(2-페닐이미다졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(4) 1-부틸-3-(2-메틸-1-프로필)-2,5-디옥소-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(5) (3S)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1-프로필-1,4,9-트리아자스피로[5.5]운데칸,(6) (3R)-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1-프로필-1,4,9-트리아자스피로[5.5]운데칸,(7) 1-부틸-9-((3,5-디메틸-1-페닐)-4-피라졸릴)메틸)-2,5-디옥소-3-(2-메틸-1-프로필)-1,4,9-트리아자스피로[5.5]운데칸,(8) 1-부틸-3-시클로헥실메틸-2,5-디옥소-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(9) 9-(1,4-벤조디옥산-6-일메틸)-1-부틸-3-(2-메틸-1-프로필)-2,5-디옥소-1,4,9-트리아자스피로[5.5]운데칸,(10) 9-(4-벤질옥시페닐메틸)-1-부틸-2,5-디옥소-3-(2-메틸-1-프로필)-1,4,9-트리아자스피로[5.5]운데칸,(11) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐헥실)-1,4,9-트리아자스피로[5.5]운데칸,(12) (3S)-1-(2-메틸프로필)-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸,(13) (3S)-1-프로필-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸,(14) (3R)-1-프로필-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸,(15) (3S)-1-프로필-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸,(16) (3R)-1-프로필-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(3-페닐프로필)-1,4,9-트리아자스피로[5.5]운데칸,(17) (3S)-1-프로필-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸,(18) (3R)-1-프로필-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸,(19) (3S)-1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸,(20) (3R)-1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸,(21) (3S)-1-프로필-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(2-(2-페닐-5-메틸옥사졸-4-일)에틸)-1,4,9-트리아자스피로[5.5]운데칸,(22) (3S)-1-프로필-2,5-디옥소-3-(4-(N-(2-클로로페닐메틸)옥시카르보닐)아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸,(23) (3S)-1-프로필-2,5-디옥소-3-[3-(3-(2,4,6-트리메틸페닐설포닐)구아니디노)프로필]-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸,(24) 1-프로필-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(25) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(26) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-알릴옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(27) (3S)-1-프로필-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-2,5-디옥소-3-(2-메틸-1-프로필)-1,4,9-트리아자스피로[5.5]운데칸,(28) (3R)-1-프로필-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-2,5-디옥소-3-(2-메틸-1-프로필)-1,4,9-트리아자스피로[5.5]운데칸,(29) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-페닐메틸-1,4,9-트리아자스피로[5.5]운데칸,(30) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-벤질옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸,(31) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-벤질옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸,(32) 1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(33) 1-부틸-2,5-디옥소-3-프로필-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(34) 1-부틸-2,5-디옥소-3-메톡시메틸-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(35) 1-(1-메틸프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(36) 1-(2-메틸부틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(37) 1-(2-메틸프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(38) 1-(2-디메틸아미노에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(39) 1-(2-메톡시에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(40) 1-(2-메틸티오에틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(41) 1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(42) 1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-(4-벤질옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(43) 1-벤질-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(44) 1-(3-메틸페닐메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(45) 1-(3-메틸페닐메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(46) 1-(1-메틸부틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(47) 1-(3-메틸부틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(48) 1-(2-메톡시페닐메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((3,5-디메틸-1-페닐)-4-피라졸릴)메틸)-1,4,9-트리아자스피로[5.5]운데칸,(49) 1-(3-메톡시페닐메틸)-2,5-디옥소-3-(2-메틸프로필)-9-((3,5-디메틸-1-페닐)-4-피라졸릴)메틸)-1,4,9-트리아자스피로[5.5]운데칸,(50) 1-(2-메틸페닐메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(51) 1-(3-메틸페닐메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(52) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-에틸티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(53) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-에틸푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(54) (3S)-1-부틸-2,5-디옥소-3-((1R)-1-히드록시-2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(55) (3R)-1-부틸-2,5-디옥소-3-((1S)-1-히드록시-2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(56) (3S)-1-프로필-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-알릴옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸,(57) (3S)-1-프로필-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-1,4,9-트리아자스피로[5.5]운데칸,(58) 1-프로필-2,5-디옥소-3-(2-메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸,(59) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸,(60) 1-부틸-2,5-디옥소-3-시클로헥실메틸-1,4,9-트리아자스피로[5.5]운데칸,(61) (3S)-1-프로필-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(4-디히드록시보란페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(62) (3S)-1-프로필-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(1,3-벤조디옥살란-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(63) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(1-(1,4-벤조디옥산-6-일)에틸)-1,4,9-트리아자스피로[5.5]운데칸,(64) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(1-(4-페닐옥시페닐)에틸)-1,4,9-트리아자스피로[5.5]운데칸,(65) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(1-(1,4-벤조디옥산-6-일)에틸)-1,4,9-트리아자스피로[5.5]운데칸,(66) (3S)-1-프로필-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-알릴-1,4,9-트리아자스피로[5.5]운데칸,(67) (3S)-1-프로필-2,5-디옥소-3-(4-아미노부틸)-9-페닐에틸-1,4,9-트리아자스피로[5.5]운데칸,(68) (3S)-1-프로필-2,5-디옥소-3-(4-(N-(4-페닐)페닐카르보닐)아미노부틸)-9-페닐에틸-1,4,9-트리아자스피로[5.5]운데칸,(69) 요오드화 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-메틸-9-(1-(1,4-벤조디옥산-6-일)에틸)-1,4,-디아자-9-아조니아스피로[5.5]운데칸,(70) (3S)-3-(4-(N-벤질옥시카르보닐)아미노부틸)-2,5-디옥소-9-(2-히드록시-2-페닐에틸)-1-프로필-1,4,9-트리아자스피로[5,5]운데칸,(71) (3S)-3-(4-(N-벤질옥시카르보닐)아미노부틸)-2,5-디옥소-9-(2-옥소-2-페닐에틸)-1-프로필-1,4,9-트리아자스피로[5,5]운데칸,(72) (3S)-1-(2-메틸프로필)-2,5-디옥소-3-메틸-9-알릴옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸,(73) (3S)-1-(2-메틸프로필)-2,5-디옥소-3-메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸,(74) (3S)-1-(2-메틸프로필)-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸,(75) (3S)-1-(1-벤질피페리딘-4-일)-2,5-디옥소-3-메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸,(76) (3S)-1-(1-벤질피페리딘-4-일)-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸,(77) (3S)-1-(2,2-디페닐프로필)-2,5-디옥소-3-메틸-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸,(78) (3S)-1-(2,2-디페닐프로필)-2,5-디옥소-3-(4-(N-벤질옥시카르보닐)아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸,(79) (3S)-1-프로필-2,5-디옥소-3-(4-벤질옥시페닐메틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸,(80) (3S)-1-프로필-2,5-디옥소-3-(4-(벤질카르보닐아미노)부틸)-9-(2,4,6-트리메톡시벤질)-1,4,9-트리아자스피로[5.5]운데칸,(81) (3S)-1-프로필-2,5-디옥소-3-(4-(벤질카르보닐아미노)부틸)-9-(2,2-디메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸,(82) (3S)-1-프로필-2,5-디옥소-3-(4-(벤질카르보닐아미노)부틸)-9-(3-페닐프로파노일)-1,4,9-트리아자스피로[5.5]운데칸,(83) (3S)-1-프로필-2,5-디옥소-3-(4-(벤질카르보닐아미노)부틸)-9-벤젠설포닐-1,4,9-트리아자스피로[5.5]운데칸,(84) (3S)-1-프로필-2,5-디옥소-3-(4-(벤질카르보닐아미노)부틸)-9-벤질아미노카르보닐-1,4,9-트리아자스피로[5.5]운데칸,(85) (3S)-1-프로필-2,5-디옥소-3-(4-(3-페닐프로파노일)아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸,(86) (3S)-1-프로필-2,5-디옥소-3-(4-벤젠설포닐아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸,(87) (3S)-1-프로필-2,5-디옥소-3-(4-(N-벤질카르바모일)아미노부틸)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸,(88) (3S)-1-부틸-2,5-디옥소-3-(4-메톡시페닐메틸)-9-시클로헥실메틸-1,4,9-트리아자스피로[5.5]운데칸,(89) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-(4-클로로페닐)티오펜-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(90) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-(4-메톡시페닐)티오펜-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(91) 1-((2E)-부테닐)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(92) 1-(푸란-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(93) 1-(티오펜-2-일메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(94) 1-시클로프로필메틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(95) 1-(2-플루오로페닐메틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(96) 1-(3-메틸-2-부테닐)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(97) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(퀴놀린-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(98) 1-부틸-2,5-디옥소-3-(벤질옥시카르보닐메틸)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(99) 1-(3-메틸-2-부테닐)-2,5-디옥소-3-시클로헥실메틸-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(100) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-((2E)-3-페닐-2-프로페닐)-1,4,9-트리아자스피로[5.5]운데칸,(101) (3S)-1-부틸-2,5-디옥소-3-(1,1-디메틸에틸)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(102) (3S)-1-부틸-2,5-디옥소-3-(1,1-디메틸에틸)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(103) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-메틸티아졸-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(104) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-메틸티아졸-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(105) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-메틸티아졸-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(106) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-메틸티아졸-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(107) (3R)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(108) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(109) (3R)-1-부틸-2,5-디옥소-3-((1R)-1-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(110) (3S)-1-부틸-2,5-디옥소-3-((1S)-1-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(111) 1-(2-부티닐)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(112) 1-(2-부티닐)-2,5-디옥소-3-시클로헥실메틸-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(113) 1-펜틸-2,5-디옥소-3-시클로헥실메틸-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(114) 1-(3-메톡시페닐메틸)-2,5-디옥소-3-(벤질옥시메틸)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(115) (3R)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(116) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(117) 1-부틸-2,5-디옥소-3-시클로펜틸메틸-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(118) 1-프로필-2,5-디옥소-3-(시클로헥실메틸옥시메틸)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(119) (3S)-1-부틸-2,5-디옥소-3-(1-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(120) (3R)-1-부틸-2,5-디옥소-3-(1-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(121) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-페닐메틸티오펜-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(122) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-페닐메틸티오펜-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(123) (3R)-1-부틸-2,5-디옥소-3-(2,2-디메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(124) (3S)-1-부틸-2,5-디옥소-3-(2,2-디메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(125) (3R)-1-(2-부티닐)-2,5-디옥소-3-(2,2-디메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(126) (3S)-1-(2-부티닐)-2,5-디옥소-3-(2,2-디메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(127) 1-부틸-2,5-디옥소-3-시클로헵틸메틸-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(128) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2,4,6-트리메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(129) 1-부틸-2,5-디옥소-3-(3-시클로헥실프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(130) 1-부틸-2,5-디옥소-3-(3-시클로헥실프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(131) 1-부틸-2,5-디옥소-3-(3-시클로헥실프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(132) 1-부틸-2,5-디옥소-3-(2-히드록시-2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(133) 1-(2-부티닐)-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(134) 1-(2-부티닐)-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(135) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(136) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐옥시피리딘-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(137) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-페닐옥시피리딘-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(138) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-메틸벤조모르폴린-7-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(139) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-메틸벤조모르폴린-7-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(140) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(N-메틸-N-페닐아미노)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(141) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(N-메틸-N-페닐아미노)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(142) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-(3,5-디메틸피라졸-1-일)-5-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(143) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-(3,5-디메틸피라졸-1-일)-5-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(144) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디에틸-1-(4-클로로페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(145) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디에틸-1-(4-클로로페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(146) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐옥시피리딘-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(147) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(6-페닐옥시피리딘-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(148) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(1,3-벤조디옥솔란-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(149) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(1,3-벤조디옥솔란-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(150) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-히드록시-4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(151) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-메틸티오페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(152) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(N,N-디페닐아미노)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(153) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(N,N-디페닐아미노)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(154) (3S)-1-(2-부티닐)-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(155) (3S)-1-(2-부티닐)-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(156) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(157) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-메틸페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(158) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-메틸페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(159) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-클로로페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(160) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-클로로페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(161) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-트리플루오로메틸페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(162) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-트리플루오로메틸페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(163) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디에틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(164) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디에틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(165) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-페닐티아졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(166) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐티아졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(167) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-(1,4-벤조디옥산-2-일)티아졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(168) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-트리플루오로메틸-2-(모르폴린-1-일)티아졸-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(169) 1-부틸-2,5-디옥소-3-(테트라히드로피란-4-일메틸)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(170) 1-부틸-2,5-디옥소-3-(테트라히드로피란-4-일메틸)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(171) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-카르복시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(172) 1-부틸-2,5-디옥소-3-(2-시클로헥실에틸)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(173) 1-부틸-2,5-디옥소-3-(2-시클로헥실에틸)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(174) (3R)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(175) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-메틸-2-페닐티아졸-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(176) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-(티오펜-1-일)티아졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(177) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-(피리딘-4-일)티아졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(178) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,4-디메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(179) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(180) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(피리딘-2-일)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(181) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(피리딘-3-일)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(182) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(3,5-디메틸피라졸-1-일)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(183) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(5-클로로피리딘-3-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(184) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(피리미딘-2-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(185) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(피리딘-3-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(186) 1-(2-부티닐)-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-메틸페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(187) (3R)-1-(2-부티닐)-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(188) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-히드록시페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(189) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(피리딘-2-일)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(190) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(피리딘-3-일)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(191) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-카르복시페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(192) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(피라진-2-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(193) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-카르복시페닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(194) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(피리딘-4-일)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(195) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(피리딘-2-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(196) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(나프탈렌-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(197) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(6-메톡시나프탈렌-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(198) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-카르복시페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(199) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(피리딘-4-일)푸란-2-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(200) 1-부틸-2,5-디옥소-3-시클로펜틸메틸-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(201) (3R)-1-부틸-2,5-디옥소-3-(2,2-디메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(202) (3S)-1-부틸-2,5-디옥소-3-(2,2-디메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(203) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-니트로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(204) (3R)-1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-페닐메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸,(205) (3S)-1-(테트라히드로푸란-2-일메틸)-2,5-디옥소-3-페닐메틸-9-(4-페닐부틸)-1,4,9-트리아자스피로[5.5]운데칸,(206) (3S)-1-프로필-2,5-디옥소-3-(3-(벤질옥시카르보닐아미노)프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸,(207) 1-부틸-2,5-디옥소-3-(카르복시메틸)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(208) 1-(3-히드록시부틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(209) 1-(3-히드록시프로필)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(210) 1-(2-히드록시부틸)-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(211) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-아미노페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(212) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(페닐카르보닐아미노)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(213) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-((4-메틸페닐)설포닐아미노)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(214) (3S)-1-부틸-2,5-디옥소-3-벤질옥시메틸-9-벤질옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸,(215) (3S)-1-부틸-2,5-디옥소-3-히드록시메틸-9-벤질옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸,(216) (3S)-1-부틸-2,5-디옥소-3-히드록시메틸-1,4,9-트리아자스피로[5.5]운데칸,(217) (3S)-1-부틸-2,5-디옥소-3-히드록시메틸-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(218) (3S)-1-부틸-2,5-디옥소-3-히드록시메틸-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(219) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-시클로펜틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(220) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(2-디에틸아미노에틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(221) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(2-디메틸아미노에틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(222) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-프로필옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(223) 1-(티오펜-2-일메틸)-2,5-디옥소-3-시클로헥실메틸-9-(4-시클로프로필메틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(224) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-시클로프로필메틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(225) 1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-시클로프로필메틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(226) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(디메틸아미노)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(227) 1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(디에틸아미노)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(228) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-벤질옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸,(229) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸,(230) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(5-(3-메틸-4-클로로페닐)-1-(4-메틸페닐메틸)피라졸-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(231) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-디메틸아미노페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(232) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-디에틸아미노페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(233) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-시클로헥실옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(234) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-메틸페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(235) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-메톡시페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(236) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-부틸페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(237) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(2-메틸프로필)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(238) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-플루오로페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(239) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3-히드록시-4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(240) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-플루오로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(241) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3-플루오로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(242) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-플루오로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(243) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-클로로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(244) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-클로로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(245) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3-클로로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(246) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3-메틸-4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(247) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(7-메톡시-1,3-벤조디옥솔란-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(248) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐티오페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(249) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-메틸페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(250) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3-메틸페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(251) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-메틸페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(252) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(1-메틸에틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(253) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3-플루오로-4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(254) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(2-히드록시에틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(255) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-히드록시-3-메틸페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(256) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-트리플루오로메틸옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(257) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3-메틸-5-클로로-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(258) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(6-페닐피리딘-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(259) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-메틸설포닐아미노페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(260) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-메틸설포닐아미노페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(261) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(5-메틸피리딘-2-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(262) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(6-메틸피리딘-1-옥사이드-3-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(263) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(1-(2-메틸프로필옥시카르보닐)인돌-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(264) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2-페닐-5-메틸옥사졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(265) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(테트라히드로피란-4-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(266) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(6-메틸피리딘-3-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(267) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-플루오로페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(268) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(피리딘-2-일)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(269) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-히드록시페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(270) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(2-카르복시에틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(271) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-(디메틸아미노설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(272) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(5-메틸피리딘-1-옥사이드-2-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(273) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(2-카르복시-1-에테닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(274) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-(2-카르복시-1-에테닐)페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(275) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-아미노카르보닐페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(276) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-아미노설포닐페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(277) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-벤질피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(278) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(2,4-디플루오로페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(279) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(피롤리딘-1-일메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(280) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-(모르폴린-4-일설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(281) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-(메틸아미노설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(282) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-시아노페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(283) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(디메틸아미노메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(284) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-(2-디메틸아미노에틸아미노설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸, 3(285) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3-(4-히드록시페닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(286) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(3-메톡시페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(287) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(퀴녹살린-2-일)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(288) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐카르보닐페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(289) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-(N-(2-히드록시에틸)-N-메틸아미노설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(290) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(2-페닐에틸)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(291) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(1,3,5-트리메틸피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(292) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(모르폴린-4-일메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(293) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-메틸피페라진-1-일메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸, 3(294) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-페닐설포닐페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(295) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-시클로헥실피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(296) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(3-카르복시페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(297) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(피페리딘-1-일메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(298) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-(피롤리딘-1-일설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(299) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(2,3-디히드로벤조푸란-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(300) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3,5-디메틸-1-(4-(2-히드록시에틸아미노설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(301) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(카르복시메틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(302) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(1-페닐-1-히드록시메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(303) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-히드록시피페리딘-1-일메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(304) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(3-카르복시페닐메틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(305) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(비스(메틸설포닐)아미노)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(306) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(1,4-벤조디옥산-6-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(307) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3-(3-히드록시페닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(308) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(메틸설포닐아미노)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(309) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(6-(4-메톡시페닐옥시)피리딘-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(310) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-메틸아미노카르보닐페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(311) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-클로로페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(312) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(3-(4-카르복시페닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(313) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(페닐아미노카르보닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(314) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-메틸티오페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(315) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-(4-(2-디메틸아미노에틸아미노카르보닐)페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(316) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-아미노카르보닐페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(317) (3S)-1-부틸-2,5-디옥소-3-(2-메틸프로필)-9-(4-디메틸아미노카르보닐페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(318) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-벤질옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸,(319) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-1,4,9-트리아자스피로[5.5]운데칸,(320) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-메틸페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(321) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-메톡시페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(322) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-플루오로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(323) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3-플루오로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(324) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-플루오로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(325) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3-클로로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(326) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-시클로헥실옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(327) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-메톡시-3-히드록시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(328) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-클로로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(329) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-메틸페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(330) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3-메틸페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(331) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-메틸페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(332) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-페닐티오페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(333) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3-(2-메틸프로필)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(334) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3-부틸페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(335) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-이소프로필페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(336) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-메톡시-3-플루오로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(337) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(2-히드록시에톡시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(338) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2-히드록시-3-메틸페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(339) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-클로로페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(340) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(7-메톡시-1,3-벤조디옥솔란-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(341) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3-메틸-4-메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(342) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-플루오로페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(343) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-트리플루오로메톡시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(344) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3-메틸-5-클로로-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(345) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2,3-디메틸-5-옥소-1-페닐피라졸린-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(346) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(1-(2-메틸프로필옥시카르보닐)인돌-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(347) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(5-메틸-2-페닐옥사졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(348) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-메틸설포닐아미노페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(349) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-메틸설포닐아미노페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(350) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(6-메틸피리딘-3-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(351) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(6-메틸피리딘-1-옥사이드-3-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(352) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(테트라히드로피란-4-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(353) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(6-페닐피리딘-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(354) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-플루오로페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(355) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(피리딘-2-일)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(356) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-히드록시페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(357) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(2-카르복시에틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(358) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-히드록시페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(359) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-카르복시페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(360) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-(디메틸아미노설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(361) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(5-메틸피리딘-1-옥사이드-2-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(362) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(2-카르복시-1-에티닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(363) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-((1E)-2-카르복시-1-에티닐)페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(364) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-아미노카르보닐페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(365) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-아미노설포닐페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(366) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-벤질피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(367) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(2,4-디플루오로페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(368) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(피롤리딘-1-일메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(369) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-(모르폰-4-일설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(370) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-시아노페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(371) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-(N-(2-히드록시에틸)-N-메틸아미노설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(372) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(2-페닐에틸)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(373) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(디메틸아미노메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(374) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3-(4-히드록시페닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(375) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(퀴녹살린-2-일)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(376) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(페닐카르보닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(377) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-메틸아미노설포닐페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(378) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(1,3,5-트리메틸피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(379) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(모르폴린-4-일메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(380) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(3-메톡시페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(381) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-메틸피페라진-1-일메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸, 3(382) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(피리딘-1-옥사이드-3-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(383) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-페닐설포닐페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(384) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-시클로헥실피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(385) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(3-카르복시페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(386) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(피페리딘-1-일메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(387) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-(피롤리딘-1-일설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(388) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(2,3-디히드로벤조푸란-5-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(389) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-카르복시페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(390) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-(2-히드록시에틸아미노설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(391) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3,5-디메틸-1-(4-(2-디메틸아미노에틸아미노설포닐)페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸, 3(392) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(1-히드록시-1-페닐메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(393) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(카르복시메틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(394) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-히드록시피페리딘-1-일메틸)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(395) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(3-카르복시페닐메틸옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(396) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(1,4-벤조디옥산-6-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(397) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3-(3-히드록시페닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(398) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(메틸설포닐아미노)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(399) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(6-(4-메톡시페닐)피리딘-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(400) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-메틸아미노카르보닐페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(401) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-클로로페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(402) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-비스(메틸설포닐)아미노페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(403) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(3-(4-카르복시페닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(404) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(페닐아미노카르보닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(405) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-메틸티오페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(406) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(4-(2-디메틸아미노에틸아미노카르보닐)페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(407) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-아미노카르보닐페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(408) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-(디메틸아미노카르보닐)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(409) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(410) 1-부틸-2,5-디옥소-3-(1-히드록시-2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(411) (Z)-1-부틸-2,5-디옥소-3-(2-메틸프로필리덴)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(412) (3S)-1-부틸-2,5-디옥소-3-((1R)-1-히드록시에틸)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(413) (Z)-1-부틸-2,5-디옥소-3-에틸리덴-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(414) (Z)-1-부틸-2,5-디옥소-3-(2-메틸프로필리덴)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸(415) (3R*)-1-부틸-2,5-디옥소-3-((1R*)-1-히드록시-2-메틸프로필)-9-벤질옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸,(416) (3R*)-1-부틸-2,5-디옥소-3-((1R*)-1-히드록시-2-메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸,(417) (3R*)-1-부틸-2,5-디옥소-3-((1R*)-1-히드록시-2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(418) (3R*)-1-부틸-2,5-디옥소-3-((1R*)-1-히드록시-2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(419) (3R*)-1-부틸-2,5-디옥소-3-((1R*)-1-히드록시-2-메틸프로필)-9-(6-페닐옥시피리딘-3-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(420) (3R*)-1-부틸-2,5-디옥소-3-((1R*)-1-히드록시-2-메틸프로필)-9-(4-(4-메틸페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(421) (3R*)-1-부틸-2,5-디옥소-3-((1R*)-1-히드록시-2-메틸프로필)-9-(4-시클로헥실옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(422) (3R*)-1-부틸-2,5-디옥소-3-((1R*)-1-히드록시-2-메틸프로필)-9-(4-(테트라히드로피란-4-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(423) (3R*)-1-부틸-2,5-디옥소-3-((1R*)-1-히드록시-2-메틸프로필)-9-(4-(피리딘-3-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(424) (3R*)-1-부틸-2,5-디옥소-3-((1R*)-1-히드록시-2-메틸프로필)-9-(4-이소프로필페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(425) (3R*)-1-부틸-2,5-디옥소-3-((1R*)-1-히드록시-2-메틸프로필)-9-(3,5-디메틸-1-(4-메틸페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(426) (3R*)-1-부틸-2,5-디옥소-3-((1R*)-1-히드록시-2-메틸프로필)-9-(3-메틸-5-클로로-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(427) (3R*)-1-부틸-2,5-디옥소-3-((1R*)-1-히드록시-2-메틸프로필)-9-(4-(4-카르복시페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(428) (3R*)-1-부틸-2,5-디옥소-3-((1R*)-1-히드록시-2-메틸프로필)-9-(3,5-디메틸-1-(피리딘-2-일)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(429) (3R*)-1-부틸-2,5-디옥소-3-((1R*)-1-히드록시-2-메틸프로필)-9-(3,5-디메틸-1-(4-카르복시페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(430) (3R*)-1-부틸-2,5-디옥소-3-((1R*)-1-히드록시-1-시클로헥실메틸)-9-벤질옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸,(431) (3R*)-1-부틸-2,5-디옥소-3-((1R*)-1-히드록시-1-시클로헥실메틸)-1,4,9-트리아자스피로[5.5]운데칸,(432) (3R*)-1-부틸-2,5-디옥소-3-((1R*)-1-히드록시-1-시클로헥실메틸)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(433) (3R*)-1-부틸-2,5-디옥소-3-((1R*)-1-히드록시-1-시클로헥실메틸)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(434) (3R*)-1-부틸-2,5-디옥소-3-((1R*)-1-히드록시-1-시클로헥실메틸)-9-(4-이소프로필페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(435) (3R*)-1-부틸-2,5-디옥소-3-((1R*)-1-히드록시-1-시클로헥실메틸)-9-(4-(6-메틸피리딘-3-일옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(436) (3R*)-1-부틸-2,5-디옥소-3-((1R*)-1-히드록시-1-시클로헥실메틸)-9-(3,5-디메틸-1-(4-플루오로페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(437) (3R*)-1-부틸-2,5-디옥소-3-((1R*)-1-히드록시-1-시클로헥실메틸)-9-(4-(4-메톡시페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(438) (3R*)-1-부틸-2,5-디옥소-3-((1R*)-1-히드록시-1-시클로헥실메틸)-9-(4-(4-플루오로페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(439) (3R*)-1-부틸-2,5-디옥소-3-((1R*)-1-히드록시-1-시클로헥실메틸)-9-(4-(4-메틸설포닐아미노페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(440) (3R*)-1-(2-부티닐)-2,5-디옥소-3-((1R*)-1-히드록시-1-시클로헥실메틸)-9-알릴옥시카르보닐-1,4,9-트리아자스피로[5.5]운데칸,(441) (3R*)-1-(2-부티닐)-2,5-디옥소-3-((1R*)-1-히드록시-1-시클로헥실메틸)-1,4,9-트리아자스피로[5.5]운데칸,(442) (3R*)-1-(2-부티닐)-2,5-디옥소-3-((1R*)-1-히드록시-1-시클로헥실메틸)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(443) (3R*)-1-(2-부티닐)-2,5-디옥소-3-((1R*)-1-히드록시-1-시클로헥실메틸)-9-(3,5-디메틸-1-(4-메틸페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(444) (3R*)-1-(2-부티닐)-2,5-디옥소-3-((1R*)-1-히드록시-1-시클로헥실메틸)-9-(4-이소프로필페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(445) (3R*)-1-(2-부티닐)-2,5-디옥소-3-((1R*)-1-히드록시-1-시클로헥실메틸)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(446) (3R*)-1-(2-부티닐)-2,5-디옥소-3-((1R*)-1-히드록시-1-시클로헥실메틸)-9-(4-(4-메틸페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(447) (3R*)-1-(2-부티닐)-2,5-디옥소-3-((1R*)-1-히드록시-1-시클로헥실메틸)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(448) (3R*)-1-(2-부티닐)-2,5-디옥소-3-((1R*)-1-히드록시-2-메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸,(449) (3R*)-1-(2-부티닐)-2,5-디옥소-3-((1R*)-1-히드록시-2-메틸프로필)-9-(3,5-디메틸-1-(4-메틸페닐)피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(450) (3R*)-1-(2-부티닐)-2,5-디옥소-3-((1R*)-1-히드록시-2-메틸프로필)-9-(4-(4-메틸페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(451) (3R*)-1-(2-부티닐)-2,5-디옥소-3-((1R*)-1-히드록시-2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(452) (3R*)-1-(2-부티닐)-2,5-디옥소-3-((1R*)-1-히드록시-2-메틸프로필)-9-(4-이소프로필페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(453) (3R*)-1-(2-부티닐)-2,5-디옥소-3-((1R*)-1-히드록시-2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(454) (3R*)-1-부틸-2,5-디옥소-3-((1S*)-1-히드록시-1-시클로헥실메틸)-9-벤질-1,4,9-트리아자스피로[5.5]운데칸,(455) (3R*)-1-부틸-2,5-디옥소-3-((1S*)-1-히드록시-1-시클로헥실메틸)-1,4,9-트리아자스피로[5.5]운데칸,(456) (3R*)-1-부틸-2,5-디옥소-3-((1S*)-1-히드록시-1-시클로헥실메틸)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(457) (3R*)-1-부틸-2,5-디옥소-3-((1S*)-1-히드록시-1-시클로헥실메틸)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(458) (3R*)-1-부틸-2,5-디옥소-3-((1S*)-1-히드록시-1-시클로헥실메틸)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(459) (3S)-1-부틸-2,5-디옥소-3-((1S)-1-히드록시-2-메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸,(460) (3S)-1-부틸-2,5-디옥소-3-((1S)-1-히드록시-2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(461) (3S)-1-부틸-2,5-디옥소-3-((1S)-1-히드록시-2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(462) (3S)-1-부틸-2,5-디옥소-3-((1S)-1-히드록시-2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(463) (3S)-1-부틸-2,5-디옥소-3-((1S)-1-히드록시-2-메틸프로필)-9-(4-(4-메틸설포닐아미노페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(464) (3R)-1-부틸-2,5-디옥소-3-((1R)-1-히드록시-2-메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸,(465) (3R)-1-부틸-2,5-디옥소-3-((1R)-1-히드록시-2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(466) (3R)-1-부틸-2,5-디옥소-3-((1R)-1-히드록시-2-메틸프로필)-9-(4-페닐옥시페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(467) (3R)-1-부틸-2,5-디옥소-3-((1R)-1-히드록시-2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(468) (3R)-1-부틸-2,5-디옥소-3-((1R)-1-히드록시-2-메틸프로필)-9-(4-(4-메틸설포닐아미노페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(469) (3R)-1-부틸-2,5-디옥소-3-((1S)-1-히드록시-2-메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸,(470) (3R)-1-부틸-2,5-디옥소-3-((1S)-1-히드록시-2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(471) (3R)-1-부틸-2,5-디옥소-3-((1S)-1-히드록시-2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(472) (3R)-1-부틸-2,5-디옥소-3-((1S)-1-히드록시-2-메틸프로필)-9-(4-(4-메틸설포닐아미노페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(473) (3S)-1-부틸-2,5-디옥소-3-((1R)-1-히드록시-2-메틸프로필)-1,4,9-트리아자스피로[5.5]운데칸,(474) (3S)-1-부틸-2,5-디옥소-3-((1R)-1-히드록시-2-메틸프로필)-9-(3,5-디메틸-1-페닐피라졸-4-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(475) (3S)-1-부틸-2,5-디옥소-3-((1R)-1-히드록시-2-메틸프로필)-9-(1,4-벤조디옥산-6-일메틸)-1,4,9-트리아자스피로[5.5]운데칸,(476) (3S)-1-부틸-2,5-디옥소-3-((1R)-1-히드록시-2-메틸프로필)-9-(4-(4-메틸설포닐아미노페닐옥시)페닐메틸)-1,4,9-트리아자스피로[5.5]운데칸,(477) (3S)-2,5-디옥소-3-(3-벤질옥시카르보닐아미노프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸,(478) (3S)-1-메틸-2,5-디옥소-3-(3-벤질옥시카르보닐아미노프로필)-9-(2-페닐에틸)-1,4,9-트리아자스피로[5.5]운데칸, 또는(479) (3S)-1-부틸-2,5-디옥소-3-시클로헥실메틸-9-(4-페닐옥시페닐메틸)-9-옥사이드-1,4,9-트리아자스피로[5.5]운데칸, 이들의 4급 암모늄염, 이들의 N-옥사이드 또는 이들의 비독성염인 화합물.
- 제1항에 기재한 화학식 I로 표시되는 트리아자스피로[5.5]운데칸 유도체, 이들의 4급 암모늄염, 이들의 N-옥사이드 또는 이들의 비독성염을 유효성분으로서 함유하는 의약 조성물.
- 제1항에 기재한 화학식 I로 표시되는 트리아자스피로[5.5]운데칸 유도체, 이들의 4급 암모늄염, 이들의 N-옥사이드 또는 이들의 비독성염을 유효성분으로서 함유하는 케모카인/케모카인 수용체 작용의 제어제.
- 제1항에 기재한 화학식 I로 표시되는 트리아자스피로[5.5]운데칸 유도체, 이들의 4급 암모늄염, 이들의 N-옥사이드 또는 이들의 비독성염을 유효성분으로서 함유하는 천식, 아토피성 피부염, 두드러기, 알레르기성 기관지 폐 아스페르길루스증, 알레르기성 호산구성 위장증, 신장염, 신장증, 간염, 관절염, 만성관절 류머티스, 건선, 비염, 결막염, 허혈 재관류 상해의 억제, 다발성 경화증, 궤양성 대장염, 급성 호흡 궁박 증후군, 세균 감염에 따른 쇼크, 당뇨병, 자기 면역 질환의 치료, 이식 장기 거부 반응, 면역 억제, 암전이 예방, 후천성 면역 부전 증후군의 예방 및/또는 치료제.
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JP2000018673 | 2000-01-27 | ||
JP2000027968 | 2000-02-04 | ||
JPJP-P-2000-00027968 | 2000-02-04 | ||
JPJP-P-2000-00147882 | 2000-05-19 | ||
JP2000147882 | 2000-05-19 | ||
PCT/JP2000/008517 WO2001040227A1 (fr) | 1999-12-03 | 2000-12-01 | Derives triazaspiro[5.5]undecane et medicaments contenant ces derives en tant que principe actif |
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US10383894B2 (en) * | 2010-03-17 | 2019-08-20 | Lutran Industries, Inc. | Human medicinal treatment using salt of peroxymonosulfuric acid |
US20130196990A1 (en) | 2010-10-06 | 2013-08-01 | Junya Qu | Benzimidazole Derivatives As PI3 Kinase Inhibitors |
US10092574B2 (en) | 2012-09-26 | 2018-10-09 | Valorisation-Recherche, Limited Partnership | Inhibitors of polynucleotide repeat-associated RNA foci and uses thereof |
EP2932533A4 (en) | 2012-12-13 | 2016-08-10 | Daniel S Marshall | MAGNETICALLY POLARIZED PHOTONIC DEVICE |
CA3034211A1 (en) | 2016-08-18 | 2018-02-22 | Vidac Pharma Ltd. | Piperazine derivatives, pharmaceutical compositions and methods of use thereof |
CN108727400B (zh) * | 2017-05-24 | 2021-07-09 | 四川晶华生物科技有限公司 | 一种治疗肿瘤的化合物 |
CN107216335B (zh) * | 2017-06-29 | 2019-04-30 | 上海药明康德新药开发有限公司 | 一种叔丁基1-(羟甲基)-3-氧杂-9-氮杂螺[5.5]十一烷-9-甲酸基酯制法 |
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CS231227B1 (en) * | 1982-10-01 | 1984-10-15 | Evzen Kasafirek | 2,5-pierazindion derivatives |
CS260899B1 (en) * | 1986-11-07 | 1989-01-12 | Evzen Kasafirek | Remedy for gastrointestinal diseases |
WO1993013101A1 (en) * | 1991-12-27 | 1993-07-08 | Yoshitomi Pharmaceutical Industries, Ltd. | Pyridonecarboxylate compound, pharmaceutical use thereof, and spiro compound |
DE69633245T2 (de) * | 1995-09-29 | 2005-09-08 | Eli Lilly And Co., Indianapolis | Spiroverbindungen als Inhibitoren der Fibrinogen-abhängigen Blutplättchenaggregation |
WO1998025605A1 (en) | 1996-12-13 | 1998-06-18 | Merck & Co., Inc. | Spiro-substituted azacycles as modulators of chemokine receptor activity |
US6288083B1 (en) * | 1998-09-04 | 2001-09-11 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
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2000
- 2000-12-01 JP JP2001540982A patent/JP4721087B2/ja not_active Expired - Fee Related
- 2000-12-01 CN CNB008187703A patent/CN1246321C/zh not_active Expired - Fee Related
- 2000-12-01 BR BR0016111-0A patent/BR0016111A/pt not_active Application Discontinuation
- 2000-12-01 AT AT00979050T patent/ATE283854T1/de not_active IP Right Cessation
- 2000-12-01 CA CA002394679A patent/CA2394679A1/en not_active Abandoned
- 2000-12-01 PT PT00979050T patent/PT1236726E/pt unknown
- 2000-12-01 AU AU16506/01A patent/AU780419C/en not_active Ceased
- 2000-12-01 ES ES00979050T patent/ES2233479T3/es not_active Expired - Lifetime
- 2000-12-01 NZ NZ519183A patent/NZ519183A/xx unknown
- 2000-12-01 MX MXPA02005465A patent/MXPA02005465A/es active IP Right Grant
- 2000-12-01 KR KR1020027007117A patent/KR100613176B1/ko not_active IP Right Cessation
- 2000-12-01 DE DE60016454T patent/DE60016454T2/de not_active Expired - Lifetime
- 2000-12-01 EP EP00979050A patent/EP1236726B1/en not_active Expired - Lifetime
- 2000-12-01 US US10/148,382 patent/US7119091B2/en not_active Expired - Fee Related
- 2000-12-01 TW TW089125555A patent/TWI224597B/zh not_active IP Right Cessation
- 2000-12-01 HU HU0300641A patent/HUP0300641A2/hu unknown
- 2000-12-01 WO PCT/JP2000/008517 patent/WO2001040227A1/ja active IP Right Grant
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2002
- 2002-05-31 NO NO20022609A patent/NO323631B1/no unknown
Also Published As
Publication number | Publication date |
---|---|
BR0016111A (pt) | 2003-03-25 |
NO20022609L (no) | 2002-07-26 |
JP4721087B2 (ja) | 2011-07-13 |
CN1433419A (zh) | 2003-07-30 |
NO323631B1 (no) | 2007-06-18 |
AU780419C (en) | 2005-09-29 |
ATE283854T1 (de) | 2004-12-15 |
US7119091B2 (en) | 2006-10-10 |
EP1236726B1 (en) | 2004-12-01 |
CA2394679A1 (en) | 2001-06-07 |
US20040097511A1 (en) | 2004-05-20 |
MXPA02005465A (es) | 2003-10-15 |
PT1236726E (pt) | 2005-04-29 |
HUP0300641A2 (hu) | 2003-06-28 |
AU1650601A (en) | 2001-06-12 |
EP1236726A4 (en) | 2003-01-15 |
KR100613176B1 (ko) | 2006-08-17 |
NO20022609D0 (no) | 2002-05-31 |
NZ519183A (en) | 2005-02-25 |
AU780419B2 (en) | 2005-03-17 |
CN1246321C (zh) | 2006-03-22 |
DE60016454D1 (de) | 2005-01-05 |
ES2233479T3 (es) | 2005-06-16 |
EP1236726A1 (en) | 2002-09-04 |
WO2001040227A1 (fr) | 2001-06-07 |
DE60016454T2 (de) | 2005-08-04 |
TWI224597B (en) | 2004-12-01 |
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