JP2005521639A5 - - Google Patents
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- Publication number
- JP2005521639A5 JP2005521639A5 JP2003543536A JP2003543536A JP2005521639A5 JP 2005521639 A5 JP2005521639 A5 JP 2005521639A5 JP 2003543536 A JP2003543536 A JP 2003543536A JP 2003543536 A JP2003543536 A JP 2003543536A JP 2005521639 A5 JP2005521639 A5 JP 2005521639A5
- Authority
- JP
- Japan
- Prior art keywords
- cyanomethyl
- trans
- cyclohexanecarboxamide
- methyl
- carboxamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 5-methoxybenzothiazol-2-ylsulfanylmethyl Chemical group 0.000 claims 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 16
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 6
- 150000003857 carboxamides Chemical class 0.000 claims 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims 2
- PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 claims 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 2
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims 2
- MPNVUMZTVITCBP-WMLDXEAASA-N (1r,2r)-2-[(4-acetamidophenyl)sulfanylmethyl]-n-(cyanomethyl)cyclohexane-1-carboxamide Chemical compound C1=CC(NC(=O)C)=CC=C1SC[C@H]1[C@H](C(=O)NCC#N)CCCC1 MPNVUMZTVITCBP-WMLDXEAASA-N 0.000 claims 1
- GOWYCZRGYJQKNM-WMLDXEAASA-N (1r,2r)-2-[(4-acetamidophenyl)sulfonylmethyl]-n-(cyanomethyl)cyclohexane-1-carboxamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)C[C@H]1[C@H](C(=O)NCC#N)CCCC1 GOWYCZRGYJQKNM-WMLDXEAASA-N 0.000 claims 1
- CUEOYJCOXOBRNN-SWLSCSKDSA-N (1r,2r)-2-[(4-bromophenyl)sulfanylmethyl]-n-(cyanomethyl)cyclohexane-1-carboxamide Chemical compound C1=CC(Br)=CC=C1SC[C@H]1[C@H](C(=O)NCC#N)CCCC1 CUEOYJCOXOBRNN-SWLSCSKDSA-N 0.000 claims 1
- GVPLUYZEWKHWIL-JLBCRZEMSA-N (1r,2r)-2-[(4-bromophenyl)sulfinylmethyl]-n-(cyanomethyl)cyclohexane-1-carboxamide Chemical compound C1=CC(Br)=CC=C1S(=O)C[C@H]1[C@H](C(=O)NCC#N)CCCC1 GVPLUYZEWKHWIL-JLBCRZEMSA-N 0.000 claims 1
- MWDVSLINUDCSQX-WCQYABFASA-N (1r,2r)-2-[(6-chloro-1,3-benzoxazol-2-yl)sulfanylmethyl]-n-(cyanomethyl)cyclohexane-1-carboxamide Chemical compound O1C2=CC(Cl)=CC=C2N=C1SC[C@@H]1CCCC[C@H]1C(=O)NCC#N MWDVSLINUDCSQX-WCQYABFASA-N 0.000 claims 1
- MWCOGYISWOGMHX-WMLDXEAASA-N (1r,2r)-2-[[3-[bis(methylsulfonyl)amino]phenyl]sulfanylmethyl]-n-(cyanomethyl)cyclohexane-1-carboxamide Chemical compound CS(=O)(=O)N(S(C)(=O)=O)C1=CC=CC(SC[C@H]2[C@@H](CCCC2)C(=O)NCC#N)=C1 MWCOGYISWOGMHX-WMLDXEAASA-N 0.000 claims 1
- LVCSGVFOJYYPKH-QFBILLFUSA-N (1r,2r)-2-[[4-(2-acetamidoethoxy)phenyl]sulfonylmethyl]-n-(cyanomethyl)cyclohexane-1-carboxamide Chemical compound C1=CC(OCCNC(=O)C)=CC=C1S(=O)(=O)C[C@H]1[C@H](C(=O)NCC#N)CCCC1 LVCSGVFOJYYPKH-QFBILLFUSA-N 0.000 claims 1
- XFWHBOWMDZQJDE-DZGCQCFKSA-N (1r,2r)-2-[[4-(2-aminoethylsulfanyl)-3-fluorophenyl]sulfonylmethyl]-n-(cyanomethyl)cyclohexane-1-carboxamide Chemical compound C1=C(F)C(SCCN)=CC=C1S(=O)(=O)C[C@H]1[C@H](C(=O)NCC#N)CCCC1 XFWHBOWMDZQJDE-DZGCQCFKSA-N 0.000 claims 1
- OMVXBBLIPPSRFP-WMLDXEAASA-N (1r,2r)-2-[[4-(2-aminoethylsulfanyl)phenyl]sulfonylmethyl]-n-(cyanomethyl)cyclohexane-1-carboxamide Chemical compound C1=CC(SCCN)=CC=C1S(=O)(=O)C[C@H]1[C@H](C(=O)NCC#N)CCCC1 OMVXBBLIPPSRFP-WMLDXEAASA-N 0.000 claims 1
- BYUMFVWIHSQRQJ-WMLDXEAASA-N (1r,2r)-2-[[4-(2-bromoethylsulfanyl)phenyl]sulfonylmethyl]-n-(cyanomethyl)cyclohexane-1-carboxamide Chemical compound C1=CC(SCCBr)=CC=C1S(=O)(=O)C[C@H]1[C@H](C(=O)NCC#N)CCCC1 BYUMFVWIHSQRQJ-WMLDXEAASA-N 0.000 claims 1
- QXGUTSIWPPOKGC-GHTZIAJQSA-N (1r,2r)-2-[[4-(3-aminophenyl)phenyl]sulfonylmethyl]-n-(cyanomethyl)cyclohexane-1-carboxamide Chemical compound NC1=CC=CC(C=2C=CC(=CC=2)S(=O)(=O)C[C@H]2[C@@H](CCCC2)C(=O)NCC#N)=C1 QXGUTSIWPPOKGC-GHTZIAJQSA-N 0.000 claims 1
- PLYMIVPRPWOEBH-JTHBVZDNSA-N (1r,2r)-2-[[4-(benzylsulfanylmethyl)phenyl]sulfonylmethyl]-n-(cyanomethyl)cyclohexane-1-carboxamide Chemical compound N#CCNC(=O)[C@@H]1CCCC[C@H]1CS(=O)(=O)C(C=C1)=CC=C1CSCC1=CC=CC=C1 PLYMIVPRPWOEBH-JTHBVZDNSA-N 0.000 claims 1
- ZBUKIDMUQWVRFZ-JTHBVZDNSA-N (1r,2r)-2-[[4-(benzylsulfonylmethyl)phenyl]sulfonylmethyl]-n-(cyanomethyl)cyclohexane-1-carboxamide Chemical compound N#CCNC(=O)[C@@H]1CCCC[C@H]1CS(=O)(=O)C(C=C1)=CC=C1CS(=O)(=O)CC1=CC=CC=C1 ZBUKIDMUQWVRFZ-JTHBVZDNSA-N 0.000 claims 1
- LTFLZUJXJIHVGS-NZQKXSOJSA-N (1r,2r)-2-[[4-[2-(4-tert-butylpiperazin-1-yl)-2-oxoethoxy]phenyl]sulfonylmethyl]-n-(cyanomethyl)cyclohexane-1-carboxamide Chemical compound C1CN(C(C)(C)C)CCN1C(=O)COC1=CC=C(S(=O)(=O)C[C@H]2[C@@H](CCCC2)C(=O)NCC#N)C=C1 LTFLZUJXJIHVGS-NZQKXSOJSA-N 0.000 claims 1
- KYZMJSFJVHTICP-NZQKXSOJSA-N (1r,2r)-2-[[4-[2-(4-tert-butylpiperazin-1-yl)-2-oxoethyl]sulfanylphenyl]sulfonylmethyl]-n-(cyanomethyl)cyclohexane-1-carboxamide Chemical compound C1CN(C(C)(C)C)CCN1C(=O)CSC1=CC=C(S(=O)(=O)C[C@H]2[C@@H](CCCC2)C(=O)NCC#N)C=C1 KYZMJSFJVHTICP-NZQKXSOJSA-N 0.000 claims 1
- HNKRTZONTWEAGK-RBJSKKJNSA-N (1r,2r)-2-[[4-[2-[(1-benzylpiperidin-4-yl)amino]-2-oxoethyl]sulfanylphenyl]sulfonylmethyl]-n-(cyanomethyl)cyclohexane-1-carboxamide Chemical compound C1CN(CC=2C=CC=CC=2)CCC1NC(=O)CSC(C=C1)=CC=C1S(=O)(=O)C[C@@H]1CCCC[C@H]1C(=O)NCC#N HNKRTZONTWEAGK-RBJSKKJNSA-N 0.000 claims 1
- DXLNYEAFXOGNGX-SIKLNZKXSA-N (1r,2r)-2-[[4-[2-[(2-chlorophenyl)methylamino]-2-oxoethyl]sulfanylphenyl]sulfonylmethyl]-n-(cyanomethyl)cyclohexane-1-carboxamide Chemical compound ClC1=CC=CC=C1CNC(=O)CSC1=CC=C(S(=O)(=O)C[C@H]2[C@@H](CCCC2)C(=O)NCC#N)C=C1 DXLNYEAFXOGNGX-SIKLNZKXSA-N 0.000 claims 1
- SPCMSXLCKGITFQ-WMZHIEFXSA-N (1r,2r)-2-[[4-[2-[(4-chlorophenyl)methylamino]-2-oxoethyl]sulfanylphenyl]sulfonylmethyl]-n-(cyanomethyl)cyclohexane-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1CNC(=O)CSC1=CC=C(S(=O)(=O)C[C@H]2[C@@H](CCCC2)C(=O)NCC#N)C=C1 SPCMSXLCKGITFQ-WMZHIEFXSA-N 0.000 claims 1
- OASMPANMFOSPSQ-QNZPCDNOSA-N (1r,2r)-2-[benzenesulfonyl(3-hydroxypropylsulfanyl)methyl]-n-(cyanomethyl)cyclohexane-1-carboxamide Chemical compound C=1C=CC=CC=1S(=O)(=O)C(SCCCO)[C@@H]1CCCC[C@H]1C(=O)NCC#N OASMPANMFOSPSQ-QNZPCDNOSA-N 0.000 claims 1
- ZBFAASATUJTIAP-WMZHIEFXSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-[[4-(2-pyridin-2-ylethylsulfanyl)phenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound O=C([C@H]1[C@@H](CCCC1)CS(=O)(=O)C=1C=CC(SCCC=2N=CC=CC=2)=CC=1)NC1(C#N)CC1 ZBFAASATUJTIAP-WMZHIEFXSA-N 0.000 claims 1
- JWPRDRIEUSMKAA-WDEREUQCSA-N (1r,2r)-n-(cyanomethyl)-2-(4,5-dihydro-1,3-thiazol-2-ylsulfanylmethyl)cyclohexane-1-carboxamide Chemical compound N#CCNC(=O)[C@@H]1CCCC[C@H]1CSC1=NCCS1 JWPRDRIEUSMKAA-WDEREUQCSA-N 0.000 claims 1
- ZRVXDEOEFFGRML-DZGCQCFKSA-N (1r,2r)-n-(cyanomethyl)-2-(cyclohexylsulfanylmethyl)cyclohexane-1-carboxamide Chemical compound N#CCNC(=O)[C@@H]1CCCC[C@H]1CSC1CCCCC1 ZRVXDEOEFFGRML-DZGCQCFKSA-N 0.000 claims 1
- OTGXOJZOQQUACM-DZGCQCFKSA-N (1r,2r)-n-(cyanomethyl)-2-[(3,4-dimethoxyphenyl)sulfanylmethyl]cyclohexane-1-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1SC[C@H]1[C@H](C(=O)NCC#N)CCCC1 OTGXOJZOQQUACM-DZGCQCFKSA-N 0.000 claims 1
- XVKGRLLQIXJXOE-XJKSGUPXSA-N (1r,2r)-n-(cyanomethyl)-2-[(3-formamidophenyl)sulfanylmethyl]cyclohexane-1-carboxamide Chemical compound O=CNC1=CC=CC(SC[C@H]2[C@@H](CCCC2)C(=O)NCC#N)=C1 XVKGRLLQIXJXOE-XJKSGUPXSA-N 0.000 claims 1
- NHRZVOLUOQKOEF-SWLSCSKDSA-N (1r,2r)-n-(cyanomethyl)-2-[(4-fluorophenyl)sulfanylmethyl]cyclohexane-1-carboxamide Chemical compound C1=CC(F)=CC=C1SC[C@H]1[C@H](C(=O)NCC#N)CCCC1 NHRZVOLUOQKOEF-SWLSCSKDSA-N 0.000 claims 1
- XESRYDKCSDPZPR-SWLSCSKDSA-N (1r,2r)-n-(cyanomethyl)-2-[(4-fluorophenyl)sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)C[C@H]1[C@H](C(=O)NCC#N)CCCC1 XESRYDKCSDPZPR-SWLSCSKDSA-N 0.000 claims 1
- PDFPDVMIGJMOAQ-SWLSCSKDSA-N (1r,2r)-n-(cyanomethyl)-2-[(4-hydroxyphenyl)sulfanylmethyl]cyclohexane-1-carboxamide Chemical compound C1=CC(O)=CC=C1SC[C@H]1[C@H](C(=O)NCC#N)CCCC1 PDFPDVMIGJMOAQ-SWLSCSKDSA-N 0.000 claims 1
- BUSLNAOPSCABPK-DOTOQJQBSA-N (1r,2r)-n-(cyanomethyl)-2-[(4-methoxyphenyl)methylsulfanylmethyl]cyclohexane-1-carboxamide Chemical compound C1=CC(OC)=CC=C1CSC[C@H]1[C@H](C(=O)NCC#N)CCCC1 BUSLNAOPSCABPK-DOTOQJQBSA-N 0.000 claims 1
- YZKKSQXINNPWGB-DOTOQJQBSA-N (1r,2r)-n-(cyanomethyl)-2-[(4-methoxyphenyl)methylsulfonylmethyl]cyclohexane-1-carboxamide Chemical compound C1=CC(OC)=CC=C1CS(=O)(=O)C[C@H]1[C@H](C(=O)NCC#N)CCCC1 YZKKSQXINNPWGB-DOTOQJQBSA-N 0.000 claims 1
- IOHWCGXHJMYENL-SWLSCSKDSA-N (1r,2r)-n-(cyanomethyl)-2-[(4-methoxyphenyl)sulfanylmethyl]cyclopentane-1-carboxamide Chemical compound C1=CC(OC)=CC=C1SC[C@H]1[C@H](C(=O)NCC#N)CCC1 IOHWCGXHJMYENL-SWLSCSKDSA-N 0.000 claims 1
- YSZNEWUCGOECCV-XJKSGUPXSA-N (1r,2r)-n-(cyanomethyl)-2-[(4-methylsulfanylphenyl)sulfanylmethyl]cyclohexane-1-carboxamide Chemical compound C1=CC(SC)=CC=C1SC[C@H]1[C@H](C(=O)NCC#N)CCCC1 YSZNEWUCGOECCV-XJKSGUPXSA-N 0.000 claims 1
- RSFFBAMJCVMIMO-SWLSCSKDSA-N (1r,2r)-n-(cyanomethyl)-2-[(4-methylsulfanylphenyl)sulfanylmethyl]cyclopentane-1-carboxamide Chemical compound C1=CC(SC)=CC=C1SC[C@H]1[C@H](C(=O)NCC#N)CCC1 RSFFBAMJCVMIMO-SWLSCSKDSA-N 0.000 claims 1
- CFBDLITUAFRXGT-XJKSGUPXSA-N (1r,2r)-n-(cyanomethyl)-2-[(4-methylsulfanylphenyl)sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound C1=CC(SC)=CC=C1S(=O)(=O)C[C@H]1[C@H](C(=O)NCC#N)CCCC1 CFBDLITUAFRXGT-XJKSGUPXSA-N 0.000 claims 1
- BNLGNOKEGUFPCV-SWLSCSKDSA-N (1r,2r)-n-(cyanomethyl)-2-[(4-methylsulfanylphenyl)sulfonylmethyl]cyclopentane-1-carboxamide Chemical compound C1=CC(SC)=CC=C1S(=O)(=O)C[C@H]1[C@H](C(=O)NCC#N)CCC1 BNLGNOKEGUFPCV-SWLSCSKDSA-N 0.000 claims 1
- GORWCWVDSXJKFT-XJKSGUPXSA-N (1r,2r)-n-(cyanomethyl)-2-[(4-methylsulfonylphenyl)sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1S(=O)(=O)C[C@H]1[C@H](C(=O)NCC#N)CCCC1 GORWCWVDSXJKFT-XJKSGUPXSA-N 0.000 claims 1
- ZPPAUOGDXHPKAU-QFBILLFUSA-N (1r,2r)-n-(cyanomethyl)-2-[(4-morpholin-4-ylphenyl)sulfanylmethyl]cyclohexane-1-carboxamide Chemical compound N#CCNC(=O)[C@@H]1CCCC[C@H]1CSC1=CC=C(N2CCOCC2)C=C1 ZPPAUOGDXHPKAU-QFBILLFUSA-N 0.000 claims 1
- GKVPGGJAKFQLLH-QFBILLFUSA-N (1r,2r)-n-(cyanomethyl)-2-[(4-morpholin-4-ylphenyl)sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound N#CCNC(=O)[C@@H]1CCCC[C@H]1CS(=O)(=O)C1=CC=C(N2CCOCC2)C=C1 GKVPGGJAKFQLLH-QFBILLFUSA-N 0.000 claims 1
- BKKXYWJVABAWOK-OXJNMPFZSA-N (1r,2r)-n-(cyanomethyl)-2-[(4-pyridin-4-ylsulfanylphenyl)sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound N#CCNC(=O)[C@@H]1CCCC[C@H]1CS(=O)(=O)C(C=C1)=CC=C1SC1=CC=NC=C1 BKKXYWJVABAWOK-OXJNMPFZSA-N 0.000 claims 1
- SGRPFTQEKZGSCN-UONOGXRCSA-N (1r,2r)-n-(cyanomethyl)-2-[(5-pyridin-4-yl-1,3,4-oxadiazol-2-yl)sulfanylmethyl]cyclohexane-1-carboxamide Chemical compound N#CCNC(=O)[C@@H]1CCCC[C@H]1CSC1=NN=C(C=2C=CN=CC=2)O1 SGRPFTQEKZGSCN-UONOGXRCSA-N 0.000 claims 1
- HKCPYPVXNNLCRF-ZMKYACIDSA-N (1r,2r)-n-(cyanomethyl)-2-[1-(4-methylsulfanylphenyl)sulfonylethyl]cyclohexane-1-carboxamide Chemical compound C1=CC(SC)=CC=C1S(=O)(=O)C(C)[C@H]1[C@H](C(=O)NCC#N)CCCC1 HKCPYPVXNNLCRF-ZMKYACIDSA-N 0.000 claims 1
- FUCZOSQYBGGTJR-XJKSGUPXSA-N (1r,2r)-n-(cyanomethyl)-2-[[3-(methanesulfonamido)phenyl]sulfanylmethyl]cyclohexane-1-carboxamide Chemical compound CS(=O)(=O)NC1=CC=CC(SC[C@H]2[C@@H](CCCC2)C(=O)NCC#N)=C1 FUCZOSQYBGGTJR-XJKSGUPXSA-N 0.000 claims 1
- DMLRPDHYXKMPHA-SWLSCSKDSA-N (1r,2r)-n-(cyanomethyl)-2-[[3-(trifluoromethyl)phenyl]sulfanylmethyl]cyclohexane-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC(SC[C@H]2[C@@H](CCCC2)C(=O)NCC#N)=C1 DMLRPDHYXKMPHA-SWLSCSKDSA-N 0.000 claims 1
- LHIKKNCZIMWBLI-SWLSCSKDSA-N (1r,2r)-n-(cyanomethyl)-2-[[3-[(2,2,2-trifluoroacetyl)amino]phenyl]sulfanylmethyl]cyclohexane-1-carboxamide Chemical compound FC(F)(F)C(=O)NC1=CC=CC(SC[C@H]2[C@@H](CCCC2)C(=O)NCC#N)=C1 LHIKKNCZIMWBLI-SWLSCSKDSA-N 0.000 claims 1
- MPXYEPKPXPQUBL-LAUBAEHRSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-(1-methylpiperidin-4-yl)oxyphenyl]sulfanylmethyl]cyclohexane-1-carboxamide Chemical compound C1CN(C)CCC1OC(C=C1)=CC=C1SC[C@H]1[C@H](C(=O)NCC#N)CCCC1 MPXYEPKPXPQUBL-LAUBAEHRSA-N 0.000 claims 1
- BFAQEMSIYVEHNI-GHTZIAJQSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-(2-morpholin-4-ylethoxy)phenyl]sulfanylmethyl]cyclohexane-1-carboxamide Chemical compound N#CCNC(=O)[C@@H]1CCCC[C@H]1CSC(C=C1)=CC=C1OCCN1CCOCC1 BFAQEMSIYVEHNI-GHTZIAJQSA-N 0.000 claims 1
- XCXPCRLPBWPVFQ-NZQKXSOJSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-(2-phenylethylsulfanyl)phenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound N#CCNC(=O)[C@@H]1CCCC[C@H]1CS(=O)(=O)C(C=C1)=CC=C1SCCC1=CC=CC=C1 XCXPCRLPBWPVFQ-NZQKXSOJSA-N 0.000 claims 1
- FLRBSYFVHXEIKM-HOGIOJOWSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-(2-phenylethylsulfinyl)phenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound N#CCNC(=O)[C@@H]1CCCC[C@H]1CS(=O)(=O)C1=CC=C(S(=O)CCC=2C=CC=CC=2)C=C1 FLRBSYFVHXEIKM-HOGIOJOWSA-N 0.000 claims 1
- HBDNFDLBUTWOHS-PGRDOPGGSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-(2-pyridin-2-ylethylsulfanyl)phenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound N#CCNC(=O)[C@@H]1CCCC[C@H]1CS(=O)(=O)C(C=C1)=CC=C1SCCC1=CC=CC=N1 HBDNFDLBUTWOHS-PGRDOPGGSA-N 0.000 claims 1
- DQYYXBRCNBGMQJ-PGRDOPGGSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-(2-pyridin-3-yloxyethylsulfanyl)phenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound N#CCNC(=O)[C@@H]1CCCC[C@H]1CS(=O)(=O)C(C=C1)=CC=C1SCCOC1=CC=CN=C1 DQYYXBRCNBGMQJ-PGRDOPGGSA-N 0.000 claims 1
- UFFRFIPFZJYODF-FXAWDEMLSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-(4-methylpiperazin-1-yl)phenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound C1CN(C)CCN1C1=CC=C(S(=O)(=O)C[C@H]2[C@@H](CCCC2)C(=O)NCC#N)C=C1 UFFRFIPFZJYODF-FXAWDEMLSA-N 0.000 claims 1
- RSASHKSTHZHSSM-GBXCKJPGSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-(4-morpholin-4-ylpiperidin-1-yl)phenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound N#CCNC(=O)[C@@H]1CCCC[C@H]1CS(=O)(=O)C1=CC=C(N2CCC(CC2)N2CCOCC2)C=C1 RSASHKSTHZHSSM-GBXCKJPGSA-N 0.000 claims 1
- ZRRPEPVUAVCTJI-SWLSCSKDSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-(difluoromethylsulfanyl)phenyl]sulfanylmethyl]cyclohexane-1-carboxamide Chemical compound C1=CC(SC(F)F)=CC=C1SC[C@H]1[C@H](C(=O)NCC#N)CCCC1 ZRRPEPVUAVCTJI-SWLSCSKDSA-N 0.000 claims 1
- FQNAXXRLRRWPLK-WMLDXEAASA-N (1r,2r)-n-(cyanomethyl)-2-[[4-(dimethylamino)phenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1S(=O)(=O)C[C@H]1[C@H](C(=O)NCC#N)CCCC1 FQNAXXRLRRWPLK-WMLDXEAASA-N 0.000 claims 1
- XFORUVQHYHZLCN-OXJNMPFZSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-(furan-2-ylmethylsulfanyl)phenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound N#CCNC(=O)[C@@H]1CCCC[C@H]1CS(=O)(=O)C(C=C1)=CC=C1SCC1=CC=CO1 XFORUVQHYHZLCN-OXJNMPFZSA-N 0.000 claims 1
- ODBRYAVFKQWYAJ-GOEBONIOSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-(hydroxymethyl)phenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound C1=CC(CO)=CC=C1S(=O)(=O)C[C@H]1[C@H](C(=O)NCC#N)CCCC1 ODBRYAVFKQWYAJ-GOEBONIOSA-N 0.000 claims 1
- NMOQVCKTOKLDHJ-SWLSCSKDSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-(trifluoromethoxy)phenyl]sulfanylmethyl]cyclohexane-1-carboxamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1SC[C@H]1[C@H](C(=O)NCC#N)CCCC1 NMOQVCKTOKLDHJ-SWLSCSKDSA-N 0.000 claims 1
- XQRIBTQQZCQIMC-SWLSCSKDSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-(trifluoromethyl)phenyl]sulfanylmethyl]cyclohexane-1-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1SC[C@H]1[C@H](C(=O)NCC#N)CCCC1 XQRIBTQQZCQIMC-SWLSCSKDSA-N 0.000 claims 1
- SIRAQOCOLDQQPV-SWLSCSKDSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-(trifluoromethyl)phenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1S(=O)(=O)C[C@H]1[C@H](C(=O)NCC#N)CCCC1 SIRAQOCOLDQQPV-SWLSCSKDSA-N 0.000 claims 1
- DXTALCVYVMMPSW-KXXXGBTESA-N (1r,2r)-n-(cyanomethyl)-2-[[4-[(1-methylpyrrolidin-2-yl)methoxy]phenyl]sulfanylmethyl]cyclohexane-1-carboxamide Chemical compound CN1CCCC1COC(C=C1)=CC=C1SC[C@H]1[C@H](C(=O)NCC#N)CCCC1 DXTALCVYVMMPSW-KXXXGBTESA-N 0.000 claims 1
- CMRSIRMDVMEIQT-MAUKXSAKSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-[2-(2,2,2-trifluoroethylamino)ethylsulfanyl]phenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound C1=CC(SCCNCC(F)(F)F)=CC=C1S(=O)(=O)C[C@H]1[C@H](C(=O)NCC#N)CCCC1 CMRSIRMDVMEIQT-MAUKXSAKSA-N 0.000 claims 1
- KLHJIAUJTMTXHE-DOTOQJQBSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-[2-(ethylsulfonylamino)ethylsulfanyl]-3-fluorophenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound C1=C(F)C(SCCNS(=O)(=O)CC)=CC=C1S(=O)(=O)C[C@H]1[C@H](C(=O)NCC#N)CCCC1 KLHJIAUJTMTXHE-DOTOQJQBSA-N 0.000 claims 1
- YQKPTIANKAJPFP-GHTZIAJQSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-[2-(furan-2-ylmethylamino)-2-oxoethyl]phenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound C=1C=COC=1CNC(=O)CC(C=C1)=CC=C1S(=O)(=O)C[C@@H]1CCCC[C@H]1C(=O)NCC#N YQKPTIANKAJPFP-GHTZIAJQSA-N 0.000 claims 1
- IMENQWGHAIBZFC-LAUBAEHRSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-[2-(furan-2-ylmethylamino)-2-oxoethyl]sulfanylphenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound C=1C=COC=1CNC(=O)CSC(C=C1)=CC=C1S(=O)(=O)C[C@@H]1CCCC[C@H]1C(=O)NCC#N IMENQWGHAIBZFC-LAUBAEHRSA-N 0.000 claims 1
- XYAZMOMEHGNHPZ-GBXCKJPGSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-[2-[(4-methoxyphenyl)methylamino]-2-oxoethyl]sulfanylphenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound C1=CC(OC)=CC=C1CNC(=O)CSC1=CC=C(S(=O)(=O)C[C@H]2[C@@H](CCCC2)C(=O)NCC#N)C=C1 XYAZMOMEHGNHPZ-GBXCKJPGSA-N 0.000 claims 1
- WSYKHEXXDNMQSV-QFBILLFUSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-[2-[(4-methyl-1,2,5-oxadiazol-3-yl)methylamino]-2-oxoethyl]sulfanylphenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound CC1=NON=C1CNC(=O)CSC1=CC=C(S(=O)(=O)C[C@H]2[C@@H](CCCC2)C(=O)NCC#N)C=C1 WSYKHEXXDNMQSV-QFBILLFUSA-N 0.000 claims 1
- YGAPQZJYNWIVLX-SQJMNOBHSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-[2-[[4-(dimethylamino)phenyl]methylamino]-2-oxoethyl]sulfanylphenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1CNC(=O)CSC1=CC=C(S(=O)(=O)C[C@H]2[C@@H](CCCC2)C(=O)NCC#N)C=C1 YGAPQZJYNWIVLX-SQJMNOBHSA-N 0.000 claims 1
- IOWJBCYZVGCYSK-NZQKXSOJSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-[2-oxo-2-(2-pyridin-4-ylethylamino)ethoxy]phenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound C=1C=NC=CC=1CCNC(=O)COC(C=C1)=CC=C1S(=O)(=O)C[C@@H]1CCCC[C@H]1C(=O)NCC#N IOWJBCYZVGCYSK-NZQKXSOJSA-N 0.000 claims 1
- CMOWLBVMDVKGHV-NZQKXSOJSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-[2-oxo-2-(2-pyridin-4-ylethylamino)ethyl]sulfanylphenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound C=1C=NC=CC=1CCNC(=O)CSC(C=C1)=CC=C1S(=O)(=O)C[C@@H]1CCCC[C@H]1C(=O)NCC#N CMOWLBVMDVKGHV-NZQKXSOJSA-N 0.000 claims 1
- JSVBBQBAVGASLD-PGRDOPGGSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-[2-oxo-2-(2-thiophen-2-ylethylamino)ethyl]sulfanylphenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound C=1C=CSC=1CCNC(=O)CSC(C=C1)=CC=C1S(=O)(=O)C[C@@H]1CCCC[C@H]1C(=O)NCC#N JSVBBQBAVGASLD-PGRDOPGGSA-N 0.000 claims 1
- AQJRIHLDGFRKGF-PGRDOPGGSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-[2-oxo-2-(2-thiophen-2-ylethylamino)ethyl]sulfonylphenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound C=1C=CSC=1CCNC(=O)CS(=O)(=O)C(C=C1)=CC=C1S(=O)(=O)C[C@@H]1CCCC[C@H]1C(=O)NCC#N AQJRIHLDGFRKGF-PGRDOPGGSA-N 0.000 claims 1
- KNGLLMQVPGGSTB-XUZZJYLKSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-[2-oxo-2-(4-pyridin-2-ylpiperazin-1-yl)ethyl]sulfanylphenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound C1CN(C=2N=CC=CC=2)CCN1C(=O)CSC(C=C1)=CC=C1S(=O)(=O)C[C@@H]1CCCC[C@H]1C(=O)NCC#N KNGLLMQVPGGSTB-XUZZJYLKSA-N 0.000 claims 1
- YGBFGYMNSUKYMG-NZQKXSOJSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-[2-oxo-2-(4-pyrimidin-2-ylpiperazin-1-yl)ethyl]sulfanylphenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound C1CN(C=2N=CC=CN=2)CCN1C(=O)CSC(C=C1)=CC=C1S(=O)(=O)C[C@@H]1CCCC[C@H]1C(=O)NCC#N YGBFGYMNSUKYMG-NZQKXSOJSA-N 0.000 claims 1
- WECJUYXPWMIPEN-SIKLNZKXSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-[2-oxo-2-(pyridin-3-ylmethylamino)ethyl]sulfanylphenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound C=1C=CN=CC=1CNC(=O)CSC(C=C1)=CC=C1S(=O)(=O)C[C@@H]1CCCC[C@H]1C(=O)NCC#N WECJUYXPWMIPEN-SIKLNZKXSA-N 0.000 claims 1
- ZRBOLCQXPGNFED-SIKLNZKXSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-[2-oxo-2-(pyridin-4-ylmethylamino)ethyl]sulfanylphenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound C=1C=NC=CC=1CNC(=O)CSC(C=C1)=CC=C1S(=O)(=O)C[C@@H]1CCCC[C@H]1C(=O)NCC#N ZRBOLCQXPGNFED-SIKLNZKXSA-N 0.000 claims 1
- YJHODLFRJDHMHF-FXAWDEMLSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-[3-(dimethylamino)propoxy]phenyl]sulfanylmethyl]cyclohexane-1-carboxamide Chemical compound C1=CC(OCCCN(C)C)=CC=C1SC[C@H]1[C@H](C(=O)NCC#N)CCCC1 YJHODLFRJDHMHF-FXAWDEMLSA-N 0.000 claims 1
- WZJDXOFYJBIBGC-SIKLNZKXSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-[3-(furan-2-ylmethylamino)-3-oxopropyl]phenyl]sulfanylmethyl]cyclohexane-1-carboxamide Chemical compound C=1C=COC=1CNC(=O)CCC(C=C1)=CC=C1SC[C@@H]1CCCC[C@H]1C(=O)NCC#N WZJDXOFYJBIBGC-SIKLNZKXSA-N 0.000 claims 1
- BYRNPOSRDQSAAK-SIKLNZKXSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-[3-(furan-2-ylmethylamino)-3-oxopropyl]phenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound C=1C=COC=1CNC(=O)CCC(C=C1)=CC=C1S(=O)(=O)C[C@@H]1CCCC[C@H]1C(=O)NCC#N BYRNPOSRDQSAAK-SIKLNZKXSA-N 0.000 claims 1
- GTVUEZMZGCKXHZ-SIKLNZKXSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-[4-[(2-methylpropan-2-yl)oxy]piperidin-4-yl]oxyphenyl]sulfanylmethyl]cyclohexane-1-carboxamide Chemical compound C=1C=C(SC[C@H]2[C@@H](CCCC2)C(=O)NCC#N)C=CC=1OC1(OC(C)(C)C)CCNCC1 GTVUEZMZGCKXHZ-SIKLNZKXSA-N 0.000 claims 1
- PLYCYSMMQJZKHG-SIKLNZKXSA-N (1r,2r)-n-(cyanomethyl)-2-[[4-[4-[(2-methylpropan-2-yl)oxy]piperidin-4-yl]oxyphenyl]sulfonylmethyl]cyclohexane-1-carboxamide Chemical compound C=1C=C(S(=O)(=O)C[C@H]2[C@@H](CCCC2)C(=O)NCC#N)C=CC=1OC1(OC(C)(C)C)CCNCC1 PLYCYSMMQJZKHG-SIKLNZKXSA-N 0.000 claims 1
- CISMOMZSXPMADA-SWLSCSKDSA-N (5r,6r)-n-(cyanomethyl)-5-[(4-fluorophenyl)sulfanylmethyl]spiro[2.4]heptane-6-carboxamide Chemical compound C1=CC(F)=CC=C1SC[C@H]1[C@H](C(=O)NCC#N)CC2(CC2)C1 CISMOMZSXPMADA-SWLSCSKDSA-N 0.000 claims 1
- WUPGXAJQDMHKQY-SWLSCSKDSA-N (5r,6r)-n-(cyanomethyl)-5-[(4-fluorophenyl)sulfonylmethyl]spiro[2.4]heptane-6-carboxamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)C[C@H]1[C@H](C(=O)NCC#N)CC2(CC2)C1 WUPGXAJQDMHKQY-SWLSCSKDSA-N 0.000 claims 1
- UIVATUPCWVUVIM-UHFFFAOYSA-N 1-aminocyclopropane-1-carbonitrile Chemical compound N#CC1(N)CC1 UIVATUPCWVUVIM-UHFFFAOYSA-N 0.000 claims 1
- JZADHJPAPFPHAM-UHFFFAOYSA-N 2-[(4-fluorophenyl)sulfanylmethyl]cyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCCCC1CSC1=CC=C(F)C=C1 JZADHJPAPFPHAM-UHFFFAOYSA-N 0.000 claims 1
- YXHQVQFVWRCDRC-GOEBONIOSA-N 2-[3-[[(1r,2r)-2-(cyanomethylcarbamoyl)cyclohexyl]methylsulfanyl]phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(SC[C@H]2[C@@H](CCCC2)C(=O)NCC#N)=C1 YXHQVQFVWRCDRC-GOEBONIOSA-N 0.000 claims 1
- QCNJQJJZTTZEHH-MAUKXSAKSA-N 2-[4-[[(1r,2r)-2-(cyanomethylcarbamoyl)cyclohexyl]methylsulfonyl]phenyl]sulfanylethyl methanesulfonate Chemical compound C1=CC(SCCOS(=O)(=O)C)=CC=C1S(=O)(=O)C[C@H]1[C@H](C(=O)NCC#N)CCCC1 QCNJQJJZTTZEHH-MAUKXSAKSA-N 0.000 claims 1
- YZZBGPHIPIWIQR-FXAWDEMLSA-N 2-chloro-n-[2-[4-[[(1r,2r)-2-(cyanomethylcarbamoyl)cyclohexyl]methylsulfonyl]phenyl]sulfanylethyl]pyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NCCSC1=CC=C(S(=O)(=O)C[C@H]2[C@@H](CCCC2)C(=O)NCC#N)C=C1 YZZBGPHIPIWIQR-FXAWDEMLSA-N 0.000 claims 1
- GMORVOQOIHISPT-UHFFFAOYSA-N 2-ethylhexanamide Chemical compound CCCCC(CC)C(N)=O GMORVOQOIHISPT-UHFFFAOYSA-N 0.000 claims 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 1
- GIWGDNARFSAUTC-DZGCQCFKSA-N 3-[[(1r,2r)-2-(cyanomethylcarbamoyl)cyclohexyl]methylsulfanyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(SC[C@H]2[C@@H](CCCC2)C(=O)NCC#N)=C1 GIWGDNARFSAUTC-DZGCQCFKSA-N 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
- YZGMRDRQQUBYRW-DZGCQCFKSA-N 4-[[(1r,2r)-2-(cyanomethylcarbamoyl)cyclohexyl]methylsulfanyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1SC[C@H]1[C@H](C(=O)NCC#N)CCCC1 YZGMRDRQQUBYRW-DZGCQCFKSA-N 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- YBIMKXARZPMCJM-UHFFFAOYSA-N Ic1ccc(cc1)[S](=O)=O Chemical group Ic1ccc(cc1)[S](=O)=O YBIMKXARZPMCJM-UHFFFAOYSA-N 0.000 claims 1
- LWDIHEOZPFKIFA-GHTZIAJQSA-N N#CCN(O)C(=O)[C@@H]1CCCC[C@H]1CS(=O)(=O)C(C=C1)=CC=C1OCCN1CCOCC1 Chemical compound N#CCN(O)C(=O)[C@@H]1CCCC[C@H]1CS(=O)(=O)C(C=C1)=CC=C1OCCN1CCOCC1 LWDIHEOZPFKIFA-GHTZIAJQSA-N 0.000 claims 1
- NZYICERVCCNJNR-UHFFFAOYSA-N N-(cyanomethyl)-7-[(4-fluorophenyl)sulfonylmethyl]-3-oxatricyclo[3.2.1.02,4]octane-6-carboxamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)CC1C(C(=O)NCC#N)C2CC1C1OC12 NZYICERVCCNJNR-UHFFFAOYSA-N 0.000 claims 1
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- IJXQETMNELUIPC-MAUKXSAKSA-N ethyl 2-[4-[[(1r,2r)-2-(cyanomethylcarbamoyl)cyclohexyl]methylsulfonyl]phenyl]sulfanylacetate Chemical compound C1=CC(SCC(=O)OCC)=CC=C1S(=O)(=O)C[C@H]1[C@H](C(=O)NCC#N)CCCC1 IJXQETMNELUIPC-MAUKXSAKSA-N 0.000 claims 1
- JXRXUEGSOVBMEP-UDGGGLCFSA-N ethyl 2-[4-[[(1r,2r)-2-(cyanomethylcarbamoyl)cyclohexyl]methylsulfonyl]phenyl]sulfanylpropanoate Chemical compound C1=CC(SC(C)C(=O)OCC)=CC=C1S(=O)(=O)C[C@H]1[C@H](C(=O)NCC#N)CCCC1 JXRXUEGSOVBMEP-UDGGGLCFSA-N 0.000 claims 1
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- BRPBRATXNDUDEC-GHTZIAJQSA-N n-[2-[4-[[(1r,2r)-2-(cyanomethylcarbamoyl)cyclohexyl]methylsulfonyl]phenyl]sulfanylethyl]morpholine-4-carboxamide Chemical compound N#CCNC(=O)[C@@H]1CCCC[C@H]1CS(=O)(=O)C(C=C1)=CC=C1SCCNC(=O)N1CCOCC1 BRPBRATXNDUDEC-GHTZIAJQSA-N 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 claims 1
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| AU2006227254B2 (en) * | 2005-03-21 | 2011-09-01 | Quest Diagnostics Investments Llc | Alpha ketoamide compounds as cysteine protease inhibitors |
| CA2602112A1 (en) * | 2005-03-22 | 2006-09-28 | Celera Genomics | Sulfonyl containing compounds as cysteine protease inhibitors |
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| EP0313847A3 (en) * | 1987-10-01 | 1989-11-29 | G.D. Searle & Co. | Non-peptidyl alpha-succinamidoacyl aminodiols as anti-hypertensive agents |
| JP2002539191A (ja) * | 1999-03-15 | 2002-11-19 | アクシス・ファーマシューティカルズ・インコーポレイテッド | プロテアーゼ阻害剤としての新規化合物及び組成物 |
-
2002
- 2002-11-13 CA CA002466115A patent/CA2466115A1/en not_active Abandoned
- 2002-11-13 US US10/495,387 patent/US7371747B2/en not_active Expired - Fee Related
- 2002-11-13 AU AU2002352663A patent/AU2002352663B2/en not_active Ceased
- 2002-11-13 AT AT02789611T patent/ATE387197T1/de not_active IP Right Cessation
- 2002-11-13 DE DE60225316T patent/DE60225316T2/de not_active Expired - Lifetime
- 2002-11-13 WO PCT/US2002/036352 patent/WO2003041649A2/en not_active Ceased
- 2002-11-13 JP JP2003543536A patent/JP4343690B2/ja not_active Expired - Fee Related
- 2002-11-13 EP EP02789611A patent/EP1446115B1/en not_active Expired - Lifetime
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