JP2009534310A5 - - Google Patents
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- Publication number
- JP2009534310A5 JP2009534310A5 JP2009503181A JP2009503181A JP2009534310A5 JP 2009534310 A5 JP2009534310 A5 JP 2009534310A5 JP 2009503181 A JP2009503181 A JP 2009503181A JP 2009503181 A JP2009503181 A JP 2009503181A JP 2009534310 A5 JP2009534310 A5 JP 2009534310A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- hetero
- cycloalkyl
- aryl
- bicycloaryl
- 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.)
- Abandoned
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- 125000000217 alkyl group Chemical group 0.000 claims 416
- 125000005842 heteroatom Chemical group 0.000 claims 259
- 125000000753 cycloalkyl group Chemical group 0.000 claims 178
- -1 cyano, thio, oxy, hydroxy, carbonyloxy Chemical group 0.000 claims 140
- 125000003118 aryl group Chemical group 0.000 claims 118
- 229910052739 hydrogen Inorganic materials 0.000 claims 90
- 239000001257 hydrogen Substances 0.000 claims 90
- 150000001875 compounds Chemical class 0.000 claims 89
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 71
- 150000002431 hydrogen Chemical class 0.000 claims 65
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 64
- 150000001602 bicycloalkyls Chemical group 0.000 claims 63
- 125000003545 alkoxy group Chemical group 0.000 claims 52
- 125000005843 halogen group Chemical group 0.000 claims 52
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 51
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 49
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 41
- 125000001072 heteroaryl group Chemical group 0.000 claims 38
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 37
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 30
- 125000004104 aryloxy group Chemical group 0.000 claims 29
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 28
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 27
- 125000004429 atom Chemical group 0.000 claims 26
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 25
- 238000000034 method Methods 0.000 claims 25
- 125000003282 alkyl amino group Chemical group 0.000 claims 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 19
- 229910052760 oxygen Inorganic materials 0.000 claims 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- 229910052717 sulfur Inorganic materials 0.000 claims 15
- 125000001424 substituent group Chemical group 0.000 claims 14
- 238000001727 in vivo Methods 0.000 claims 13
- 238000000926 separation method Methods 0.000 claims 12
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 10
- 201000010099 disease Diseases 0.000 claims 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- 125000005647 linker group Chemical group 0.000 claims 8
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 239000003814 drug Substances 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 7
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 7
- 229940124597 therapeutic agent Drugs 0.000 claims 7
- 102100028255 Renin Human genes 0.000 claims 6
- 108090000783 Renin Proteins 0.000 claims 6
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 6
- 230000000694 effects Effects 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 239000000047 product Substances 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 125000005102 carbonylalkoxy group Chemical group 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 239000011593 sulfur Substances 0.000 claims 4
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims 3
- 230000008878 coupling Effects 0.000 claims 3
- 238000010168 coupling process Methods 0.000 claims 3
- 238000005859 coupling reaction Methods 0.000 claims 3
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 3
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims 3
- 239000003112 inhibitor Substances 0.000 claims 3
- 229940124530 sulfonamide Drugs 0.000 claims 3
- 150000003456 sulfonamides Chemical class 0.000 claims 3
- 125000004404 heteroalkyl group Chemical group 0.000 claims 2
- 239000012669 liquid formulation Substances 0.000 claims 2
- 239000005022 packaging material Substances 0.000 claims 2
- 230000007170 pathology Effects 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- DMGXIVUFFBNRIO-XMMPIXPASA-N (2r)-2-benzyl-1-(2,2-diphenylethylsulfonyl)piperazine Chemical compound N1([C@@H](CNCC1)CC=1C=CC=CC=1)S(=O)(=O)CC(C=1C=CC=CC=1)C1=CC=CC=C1 DMGXIVUFFBNRIO-XMMPIXPASA-N 0.000 claims 1
- WBOSATFKNXTWBU-LJQANCHMSA-N (2r)-2-benzyl-1-(2-phenylethylsulfonyl)piperazine Chemical compound N1([C@@H](CNCC1)CC=1C=CC=CC=1)S(=O)(=O)CCC1=CC=CC=C1 WBOSATFKNXTWBU-LJQANCHMSA-N 0.000 claims 1
- MVXXJEVLTRMACW-HSZRJFAPSA-N (2r)-n-benzhydryl-2-benzylpiperazine-1-carboxamide Chemical compound N1([C@@H](CNCC1)CC=1C=CC=CC=1)C(=O)NC(C=1C=CC=CC=1)C1=CC=CC=C1 MVXXJEVLTRMACW-HSZRJFAPSA-N 0.000 claims 1
- KZVIATQEEJMLIT-YLJYHZDGSA-N (3r)-1-[(2r)-2-benzylpiperazin-1-yl]-3-phenylbutan-1-one Chemical compound C([C@@H]1CNCCN1C(=O)C[C@@H](C)C=1C=CC=CC=1)C1=CC=CC=C1 KZVIATQEEJMLIT-YLJYHZDGSA-N 0.000 claims 1
- KZVIATQEEJMLIT-FXAWDEMLSA-N (3s)-1-[(2r)-2-benzylpiperazin-1-yl]-3-phenylbutan-1-one Chemical compound C([C@@H]1CNCCN1C(=O)C[C@H](C)C=1C=CC=CC=1)C1=CC=CC=C1 KZVIATQEEJMLIT-FXAWDEMLSA-N 0.000 claims 1
- NDDVYYHYUHWXRB-JOCHJYFZSA-N 1-[(2r)-2-[(4-hydroxyphenyl)methyl]piperazin-1-yl]-3-(2-phenoxyphenyl)propan-1-one Chemical compound C1=CC(O)=CC=C1C[C@H]1N(C(=O)CCC=2C(=CC=CC=2)OC=2C=CC=CC=2)CCNC1 NDDVYYHYUHWXRB-JOCHJYFZSA-N 0.000 claims 1
- UKLLZURNGIRXHW-IKOFQBKESA-N 1-[(2r)-2-benzylpiperazin-1-yl]-2,3-diphenylpropan-1-one Chemical compound N1([C@@H](CNCC1)CC=1C=CC=CC=1)C(=O)C(C=1C=CC=CC=1)CC1=CC=CC=C1 UKLLZURNGIRXHW-IKOFQBKESA-N 0.000 claims 1
- RRKJVOPFAAKRJG-GEPVFLLWSA-N 1-[(2r)-2-benzylpiperazin-1-yl]-2-(2,2-dimethyl-4-phenyloxan-4-yl)ethanone Chemical compound C1COC(C)(C)CC1(C=1C=CC=CC=1)CC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 RRKJVOPFAAKRJG-GEPVFLLWSA-N 0.000 claims 1
- OJKIRTLFONOTAY-MRXNPFEDSA-N 1-[(2r)-2-benzylpiperazin-1-yl]-2-(2-bromophenoxy)ethanone Chemical compound BrC1=CC=CC=C1OCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 OJKIRTLFONOTAY-MRXNPFEDSA-N 0.000 claims 1
- YWMJSUBSGIPHJS-QGZVFWFLSA-N 1-[(2r)-2-benzylpiperazin-1-yl]-2-(2-methoxyphenoxy)ethanone Chemical compound COC1=CC=CC=C1OCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 YWMJSUBSGIPHJS-QGZVFWFLSA-N 0.000 claims 1
- VOTJDEFFGRTQAS-JOCHJYFZSA-N 1-[(2r)-2-benzylpiperazin-1-yl]-2-(2-phenoxyphenyl)ethanone Chemical compound N1([C@@H](CNCC1)CC=1C=CC=CC=1)C(=O)CC1=CC=CC=C1OC1=CC=CC=C1 VOTJDEFFGRTQAS-JOCHJYFZSA-N 0.000 claims 1
- PNMYTMLDYWVFMD-OAQYLSRUSA-N 1-[(2r)-2-benzylpiperazin-1-yl]-2-[2-(2-chlorophenyl)phenyl]ethanone Chemical compound ClC1=CC=CC=C1C1=CC=CC=C1CC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 PNMYTMLDYWVFMD-OAQYLSRUSA-N 0.000 claims 1
- AXYJUPGWWMLPQK-JOCHJYFZSA-N 1-[(2r)-2-benzylpiperazin-1-yl]-2-[2-(2-methoxyphenyl)phenyl]ethanone Chemical compound COC1=CC=CC=C1C1=CC=CC=C1CC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 AXYJUPGWWMLPQK-JOCHJYFZSA-N 0.000 claims 1
- SKFDOXWJROJNTG-HSZRJFAPSA-N 1-[(2r)-2-benzylpiperazin-1-yl]-2-[2-(4-fluorophenyl)phenyl]ethanone Chemical compound C1=CC(F)=CC=C1C1=CC=CC=C1CC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 SKFDOXWJROJNTG-HSZRJFAPSA-N 0.000 claims 1
- UIACMSYXQNQZSO-HXUWFJFHSA-N 1-[(2r)-2-benzylpiperazin-1-yl]-2-naphthalen-1-yloxyethanone Chemical compound C([C@@H]1CNCCN1C(COC=1C2=CC=CC=C2C=CC=1)=O)C1=CC=CC=C1 UIACMSYXQNQZSO-HXUWFJFHSA-N 0.000 claims 1
- SJLJGJWHVGWLQY-XMMPIXPASA-N 1-[(2r)-2-benzylpiperazin-1-yl]-3,3-diphenylpropan-1-one Chemical compound N1([C@@H](CNCC1)CC=1C=CC=CC=1)C(=O)CC(C=1C=CC=CC=1)C1=CC=CC=C1 SJLJGJWHVGWLQY-XMMPIXPASA-N 0.000 claims 1
- OBWLKOAZNZMJPR-OADZCNSWSA-N 1-[(2r)-2-benzylpiperazin-1-yl]-3-(2,2-dimethyloxan-4-yl)-3-phenylpropan-1-one Chemical compound C1COC(C)(C)CC1C(C=1C=CC=CC=1)CC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 OBWLKOAZNZMJPR-OADZCNSWSA-N 0.000 claims 1
- QQGAQPPBRQQTFW-HSZRJFAPSA-N 1-[(2r)-2-benzylpiperazin-1-yl]-3-(2-phenoxyphenyl)propan-1-one Chemical compound N1([C@@H](CNCC1)CC=1C=CC=CC=1)C(=O)CCC1=CC=CC=C1OC1=CC=CC=C1 QQGAQPPBRQQTFW-HSZRJFAPSA-N 0.000 claims 1
- QPOGZIRAADKVJP-RUZDIDTESA-N 1-[(2r)-2-benzylpiperazin-1-yl]-3-(4,5-diphenyl-1,3-oxazol-2-yl)propan-1-one Chemical compound N1([C@@H](CNCC1)CC=1C=CC=CC=1)C(=O)CCC(O1)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 QPOGZIRAADKVJP-RUZDIDTESA-N 0.000 claims 1
- OVTIKUQEADWYBA-OZAIVSQSSA-N 1-[(2r)-2-benzylpiperazin-1-yl]-3-(furan-2-yl)-4-phenylbutan-1-one Chemical compound N1([C@@H](CNCC1)CC=1C=CC=CC=1)C(=O)CC(C=1OC=CC=1)CC1=CC=CC=C1 OVTIKUQEADWYBA-OZAIVSQSSA-N 0.000 claims 1
- XZSBPBYSXCXVOR-RUZDIDTESA-N 1-[(2r)-2-benzylpiperazin-1-yl]-3-(n-phenylanilino)propan-1-one Chemical compound N1([C@@H](CNCC1)CC=1C=CC=CC=1)C(=O)CCN(C=1C=CC=CC=1)C1=CC=CC=C1 XZSBPBYSXCXVOR-RUZDIDTESA-N 0.000 claims 1
- BMTQIJUSCSGMJI-XMMPIXPASA-N 1-[(2r)-2-benzylpiperazin-1-yl]-3-[2-(3-ethoxyphenoxy)phenyl]propan-1-one Chemical compound CCOC1=CC=CC(OC=2C(=CC=CC=2)CCC(=O)N2[C@@H](CNCC2)CC=2C=CC=CC=2)=C1 BMTQIJUSCSGMJI-XMMPIXPASA-N 0.000 claims 1
- YXYCEVJHRUYTNW-OAQYLSRUSA-N 1-[(2r)-2-benzylpiperazin-1-yl]-3-[2-(3-hydroxypropoxy)phenyl]propan-1-one Chemical compound OCCCOC1=CC=CC=C1CCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 YXYCEVJHRUYTNW-OAQYLSRUSA-N 0.000 claims 1
- QPTQRSPZFBZORL-JOCHJYFZSA-N 1-[(2r)-2-benzylpiperazin-1-yl]-3-[2-(3-methoxypropoxy)phenyl]propan-1-one Chemical compound COCCCOC1=CC=CC=C1CCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 QPTQRSPZFBZORL-JOCHJYFZSA-N 0.000 claims 1
- OQUAJJKMCMNCHE-XMMPIXPASA-N 1-[(2r)-2-benzylpiperazin-1-yl]-3-[2-(3-methylphenoxy)phenyl]propan-1-one Chemical compound CC1=CC=CC(OC=2C(=CC=CC=2)CCC(=O)N2[C@@H](CNCC2)CC=2C=CC=CC=2)=C1 OQUAJJKMCMNCHE-XMMPIXPASA-N 0.000 claims 1
- BSWWSRLOKRWFAC-HSZRJFAPSA-N 1-[(2r)-2-benzylpiperazin-1-yl]-3-[2-(4-chlorophenoxy)phenyl]propan-1-one Chemical compound C1=CC(Cl)=CC=C1OC1=CC=CC=C1CCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 BSWWSRLOKRWFAC-HSZRJFAPSA-N 0.000 claims 1
- NCOUSDXFCGNXDA-HSZRJFAPSA-N 1-[(2r)-2-benzylpiperazin-1-yl]-3-[2-(4-methoxyphenoxy)phenyl]propan-1-one Chemical compound C1=CC(OC)=CC=C1OC1=CC=CC=C1CCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 NCOUSDXFCGNXDA-HSZRJFAPSA-N 0.000 claims 1
- CLECYELPSFRQMY-XMMPIXPASA-N 1-[(2r)-2-benzylpiperazin-1-yl]-3-[2-(4-methylphenoxy)phenyl]propan-1-one Chemical compound C1=CC(C)=CC=C1OC1=CC=CC=C1CCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 CLECYELPSFRQMY-XMMPIXPASA-N 0.000 claims 1
- CMABIVSVGHNAIA-AREMUKBSSA-N 1-[(2r)-2-benzylpiperazin-1-yl]-3-[2-[(4-chlorophenyl)methyl]phenyl]propan-1-one Chemical compound C1=CC(Cl)=CC=C1CC1=CC=CC=C1CCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 CMABIVSVGHNAIA-AREMUKBSSA-N 0.000 claims 1
- KMIUZTQAADEBQM-XMMPIXPASA-N 1-[(2r)-2-benzylpiperazin-1-yl]-3-[2-[2-(hydroxymethyl)phenoxy]phenyl]propan-1-one Chemical compound OCC1=CC=CC=C1OC1=CC=CC=C1CCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 KMIUZTQAADEBQM-XMMPIXPASA-N 0.000 claims 1
- LRVIXVIELXCRET-XMMPIXPASA-N 1-[(2r)-2-benzylpiperazin-1-yl]-3-[2-[3-(2-methoxyethoxy)propoxy]phenyl]propan-1-one Chemical compound COCCOCCCOC1=CC=CC=C1CCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 LRVIXVIELXCRET-XMMPIXPASA-N 0.000 claims 1
- BDYSKYRVHCNVRL-RUZDIDTESA-N 1-[(2r)-2-benzylpiperazin-1-yl]-3-[2-[3-(dimethylamino)phenoxy]phenyl]propan-1-one Chemical compound CN(C)C1=CC=CC(OC=2C(=CC=CC=2)CCC(=O)N2[C@@H](CNCC2)CC=2C=CC=CC=2)=C1 BDYSKYRVHCNVRL-RUZDIDTESA-N 0.000 claims 1
- KGDBCQOZRMQJHL-XMMPIXPASA-N 1-[(2r)-2-benzylpiperazin-1-yl]-3-[2-[3-(hydroxymethyl)phenoxy]phenyl]propan-1-one Chemical compound OCC1=CC=CC(OC=2C(=CC=CC=2)CCC(=O)N2[C@@H](CNCC2)CC=2C=CC=CC=2)=C1 KGDBCQOZRMQJHL-XMMPIXPASA-N 0.000 claims 1
- KPYHSXPTARFBKL-OAQYLSRUSA-N 1-[(2r)-2-benzylpiperazin-1-yl]-3-[4-(4-chlorophenyl)-2-methyl-1,3-oxazol-5-yl]propan-1-one Chemical compound C([C@@H]1CNCCN1C(=O)CCC1=C(N=C(O1)C)C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 KPYHSXPTARFBKL-OAQYLSRUSA-N 0.000 claims 1
- CBBLSYFZUKNIJM-LJQANCHMSA-N 1-[(2r)-2-benzylpiperazin-1-yl]-3-phenylpropan-1-one Chemical compound N1([C@@H](CNCC1)CC=1C=CC=CC=1)C(=O)CCC1=CC=CC=C1 CBBLSYFZUKNIJM-LJQANCHMSA-N 0.000 claims 1
- DVNIBKSKHKGDIV-HXUWFJFHSA-N 1-[(2r)-2-benzylpiperazin-1-yl]-4-phenylbutan-1-one Chemical compound N1([C@@H](CNCC1)CC=1C=CC=CC=1)C(=O)CCCC1=CC=CC=C1 DVNIBKSKHKGDIV-HXUWFJFHSA-N 0.000 claims 1
- ANDYEFOXEVPHDV-LJQANCHMSA-N 1-[(2r)-2-benzylpiperazin-1-yl]-4-phenylbutane-1,4-dione Chemical compound N1([C@@H](CNCC1)CC=1C=CC=CC=1)C(=O)CCC(=O)C1=CC=CC=C1 ANDYEFOXEVPHDV-LJQANCHMSA-N 0.000 claims 1
- ZEPOAISTXFKUCY-XMMPIXPASA-N 2-(3-benzylphenoxy)-1-[(2r)-2-benzylpiperazin-1-yl]ethanone Chemical compound N1([C@@H](CNCC1)CC=1C=CC=CC=1)C(=O)COC(C=1)=CC=CC=1CC1=CC=CC=C1 ZEPOAISTXFKUCY-XMMPIXPASA-N 0.000 claims 1
- ZBVVLDFDTCTVNI-XMMPIXPASA-N 2-[2-[3-[(2r)-2-benzylpiperazin-1-yl]-3-oxopropyl]phenoxy]benzonitrile Chemical compound N1([C@@H](CNCC1)CC=1C=CC=CC=1)C(=O)CCC1=CC=CC=C1OC1=CC=CC=C1C#N ZBVVLDFDTCTVNI-XMMPIXPASA-N 0.000 claims 1
- FSVQKSKFGOIHIQ-CSMDKSQMSA-N 2-[3-[(2r)-2-benzylpiperazin-1-yl]-1-(4-methylphenyl)-3-oxopropyl]-3h-isoindol-1-one Chemical compound C1=CC(C)=CC=C1C(N1C(C2=CC=CC=C2C1)=O)CC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 FSVQKSKFGOIHIQ-CSMDKSQMSA-N 0.000 claims 1
- VZZYBRHPVYAECC-GEPVFLLWSA-N 2-[3-[(2r)-2-benzylpiperazin-1-yl]-3-oxopropyl]-2-phenylcyclohexan-1-one Chemical compound N1([C@@H](CNCC1)CC=1C=CC=CC=1)C(=O)CCC1(C=2C=CC=CC=2)CCCCC1=O VZZYBRHPVYAECC-GEPVFLLWSA-N 0.000 claims 1
- GCGLCPWSRCFUGB-HSZRJFAPSA-N 2-[4-[[(2r)-1-[3-(2-phenoxyphenyl)propanoyl]piperazin-2-yl]methyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1C[C@H]1N(C(=O)CCC=2C(=CC=CC=2)OC=2C=CC=CC=2)CCNC1 GCGLCPWSRCFUGB-HSZRJFAPSA-N 0.000 claims 1
- IIHDALCSCVIQCY-SSEXGKCCSA-N 2-[4-[[(2r)-1-[3-[2-[[2-(2-acetamidoethyl)phenyl]methyl]phenyl]propanoyl]piperazin-2-yl]methyl]phenoxy]acetamide Chemical compound CC(=O)NCCC1=CC=CC=C1CC1=CC=CC=C1CCC(=O)N1[C@H](CC=2C=CC(OCC(N)=O)=CC=2)CNCC1 IIHDALCSCVIQCY-SSEXGKCCSA-N 0.000 claims 1
- QWXGIFRCIWUSTP-SSEXGKCCSA-N 2-[4-[[(2r)-1-[3-[2-[[2-(2-acetamidoethyl)phenyl]methyl]phenyl]propanoyl]piperazin-2-yl]methyl]phenoxy]acetic acid Chemical compound CC(=O)NCCC1=CC=CC=C1CC1=CC=CC=C1CCC(=O)N1[C@H](CC=2C=CC(OCC(O)=O)=CC=2)CNCC1 QWXGIFRCIWUSTP-SSEXGKCCSA-N 0.000 claims 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- VMUXSMXIQBNMGZ-UHFFFAOYSA-N 3,4-dihydrocoumarin Chemical class C1=CC=C2OC(=O)CCC2=C1 VMUXSMXIQBNMGZ-UHFFFAOYSA-N 0.000 claims 1
- ZPYKCHLSGXFWLC-AREMUKBSSA-N 3-(2-benzylphenyl)-1-[(2r)-2-benzylpiperazin-1-yl]propan-1-one Chemical compound N1([C@@H](CNCC1)CC=1C=CC=CC=1)C(=O)CCC1=CC=CC=C1CC1=CC=CC=C1 ZPYKCHLSGXFWLC-AREMUKBSSA-N 0.000 claims 1
- YMTMGPRPDTVCGV-HSZRJFAPSA-N 3-(2-phenoxyphenyl)-1-[(2r)-2-[[4-(2h-tetrazol-5-ylmethoxy)phenyl]methyl]piperazin-1-yl]propan-1-one Chemical compound N1([C@@H](CNCC1)CC=1C=CC(OCC=2NN=NN=2)=CC=1)C(=O)CCC1=CC=CC=C1OC1=CC=CC=C1 YMTMGPRPDTVCGV-HSZRJFAPSA-N 0.000 claims 1
- ADODFQBMFXDJMO-RUZDIDTESA-N 3-[2-(3-acetylphenoxy)phenyl]-1-[(2r)-2-benzylpiperazin-1-yl]propan-1-one Chemical compound CC(=O)C1=CC=CC(OC=2C(=CC=CC=2)CCC(=O)N2[C@@H](CNCC2)CC=2C=CC=CC=2)=C1 ADODFQBMFXDJMO-RUZDIDTESA-N 0.000 claims 1
- XMZDDAFHHPZSFK-RUZDIDTESA-N 3-[2-[3-[(2r)-2-benzylpiperazin-1-yl]-3-oxopropyl]phenoxy]-n-ethylbenzamide Chemical compound CCNC(=O)C1=CC=CC(OC=2C(=CC=CC=2)CCC(=O)N2[C@@H](CNCC2)CC=2C=CC=CC=2)=C1 XMZDDAFHHPZSFK-RUZDIDTESA-N 0.000 claims 1
- MFTFQHQVGBKBTP-QGZVFWFLSA-N 3-[3-[(2r)-2-benzylpiperazin-1-yl]-3-oxopropyl]-1,4-benzoxazin-2-one Chemical compound C([C@@H]1CNCCN1C(CCC=1C(OC2=CC=CC=C2N=1)=O)=O)C1=CC=CC=C1 MFTFQHQVGBKBTP-QGZVFWFLSA-N 0.000 claims 1
- WDXTWLBAHVKOFS-RUZDIDTESA-N 4-[(2r)-2-benzylpiperazin-1-yl]-4-oxo-n,n-diphenylbutanamide Chemical compound C([C@@H]1CNCCN1C(=O)CCC(=O)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 WDXTWLBAHVKOFS-RUZDIDTESA-N 0.000 claims 1
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- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 206010060891 General symptom Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 claims 1
- MHVGVYNBJJBXNB-XMMPIXPASA-N [2-[3-[(2r)-2-benzylpiperazin-1-yl]-3-oxopropyl]phenyl] benzoate Chemical compound N1([C@@H](CNCC1)CC=1C=CC=CC=1)C(=O)CCC1=CC=CC=C1OC(=O)C1=CC=CC=C1 MHVGVYNBJJBXNB-XMMPIXPASA-N 0.000 claims 1
- CQEJYQKOODYVCQ-HXUWFJFHSA-N [4-[3-[(2r)-2-benzylpiperazin-1-yl]-3-oxopropyl]-2-methoxyphenyl] acetate Chemical compound C1=C(OC(C)=O)C(OC)=CC(CCC(=O)N2[C@@H](CNCC2)CC=2C=CC=CC=2)=C1 CQEJYQKOODYVCQ-HXUWFJFHSA-N 0.000 claims 1
- URAOOBLTZJEGCK-HHHXNRCGSA-N [4-[[(2r)-1-[3-(2-phenoxyphenyl)propanoyl]piperazin-2-yl]methyl]phenyl] 4-methylpiperazine-1-carboxylate Chemical compound C1CN(C)CCN1C(=O)OC(C=C1)=CC=C1C[C@H]1N(C(=O)CCC=2C(=CC=CC=2)OC=2C=CC=CC=2)CCNC1 URAOOBLTZJEGCK-HHHXNRCGSA-N 0.000 claims 1
- AQQLPCCTGGXDLI-SSEXGKCCSA-N [4-[[(2r)-1-[3-[2-[2-(2-acetamidoethyl)phenoxy]phenyl]propanoyl]piperazin-2-yl]methyl]phenyl] morpholine-4-carboxylate Chemical compound CC(=O)NCCC1=CC=CC=C1OC1=CC=CC=C1CCC(=O)N1[C@H](CC=2C=CC(OC(=O)N3CCOCC3)=CC=2)CNCC1 AQQLPCCTGGXDLI-SSEXGKCCSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000003796 beauty Effects 0.000 claims 1
- 229940047583 cetamide Drugs 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 238000001361 intraarterial administration Methods 0.000 claims 1
- 238000007918 intramuscular administration Methods 0.000 claims 1
- 238000007912 intraperitoneal administration Methods 0.000 claims 1
- 238000007913 intrathecal administration Methods 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- 239000002502 liposome Substances 0.000 claims 1
- ZMUZSNGKNCFYGD-XMMPIXPASA-N methyl 2-[4-[[(2r)-1-[3-(2-phenoxyphenyl)propanoyl]piperazin-2-yl]methyl]phenoxy]acetate Chemical compound C1=CC(OCC(=O)OC)=CC=C1C[C@H]1N(C(=O)CCC=2C(=CC=CC=2)OC=2C=CC=CC=2)CCNC1 ZMUZSNGKNCFYGD-XMMPIXPASA-N 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- JPNIJSADDGWOID-HSZRJFAPSA-N n-[1-[2-[(2r)-2-benzylpiperazin-1-yl]-2-oxoethyl]cyclohexyl]benzamide Chemical compound N1([C@@H](CNCC1)CC=1C=CC=CC=1)C(=O)CC1(NC(=O)C=2C=CC=CC=2)CCCCC1 JPNIJSADDGWOID-HSZRJFAPSA-N 0.000 claims 1
- ORZGNWOJQXZXMT-GDLZYMKVSA-N n-[2-[2-[2-[3-[(2r)-2-benzylpiperazin-1-yl]-3-oxopropyl]-4-methylphenoxy]-5-methylphenyl]ethyl]acetamide Chemical compound CC(=O)NCCC1=CC(C)=CC=C1OC1=CC=C(C)C=C1CCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 ORZGNWOJQXZXMT-GDLZYMKVSA-N 0.000 claims 1
- UOCVIUUTUZSEJL-GDLZYMKVSA-N n-[2-[2-[2-[3-[(2r)-2-benzylpiperazin-1-yl]-3-oxopropyl]-5-methylphenoxy]-5-methylphenyl]ethyl]acetamide Chemical compound CC(=O)NCCC1=CC(C)=CC=C1OC1=CC(C)=CC=C1CCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 UOCVIUUTUZSEJL-GDLZYMKVSA-N 0.000 claims 1
- WBUNNOBOGLXMRX-MUUNZHRXSA-N n-[2-[2-[2-[3-[(2r)-2-benzylpiperazin-1-yl]-3-oxopropyl]-5-methylphenoxy]phenyl]ethyl]acetamide Chemical compound CC(=O)NCCC1=CC=CC=C1OC1=CC(C)=CC=C1CCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 WBUNNOBOGLXMRX-MUUNZHRXSA-N 0.000 claims 1
- ABGPZZYBVXRMGC-MUUNZHRXSA-N n-[2-[2-[2-[3-[(2r)-2-benzylpiperazin-1-yl]-3-oxopropyl]phenoxy]-5-methylphenyl]ethyl]acetamide Chemical compound CC(=O)NCCC1=CC(C)=CC=C1OC1=CC=CC=C1CCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 ABGPZZYBVXRMGC-MUUNZHRXSA-N 0.000 claims 1
- DXGGRMQJTAFSGG-HHHXNRCGSA-N n-[2-[2-[2-[3-[(2r)-2-benzylpiperazin-1-yl]-3-oxopropyl]phenoxy]phenyl]ethyl]acetamide Chemical compound CC(=O)NCCC1=CC=CC=C1OC1=CC=CC=C1CCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 DXGGRMQJTAFSGG-HHHXNRCGSA-N 0.000 claims 1
- OIZZCQSDYYLDHR-HHHXNRCGSA-N n-[2-[2-[2-[3-[(2r)-2-benzylpiperazin-1-yl]-3-oxopropyl]phenoxy]phenyl]ethyl]propanamide Chemical compound CCC(=O)NCCC1=CC=CC=C1OC1=CC=CC=C1CCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 OIZZCQSDYYLDHR-HHHXNRCGSA-N 0.000 claims 1
- OYUBATUGACPUSL-GDLZYMKVSA-N n-[2-[2-[[2-[3-[(2r)-2-[(4-hydroxyphenyl)methyl]piperazin-1-yl]-3-oxopropyl]phenyl]methyl]phenyl]ethyl]acetamide Chemical compound CC(=O)NCCC1=CC=CC=C1CC1=CC=CC=C1CCC(=O)N1[C@H](CC=2C=CC(O)=CC=2)CNCC1 OYUBATUGACPUSL-GDLZYMKVSA-N 0.000 claims 1
- YMQQENDWBUNWGN-SSEXGKCCSA-N n-[2-[2-[[2-[3-[(2r)-2-benzylpiperazin-1-yl]-3-oxopropyl]phenyl]methyl]phenyl]ethyl]acetamide Chemical compound CC(=O)NCCC1=CC=CC=C1CC1=CC=CC=C1CCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 YMQQENDWBUNWGN-SSEXGKCCSA-N 0.000 claims 1
- PXFWMLMFLYEOEO-RUZDIDTESA-N n-[3-[2-[3-[(2r)-2-benzylpiperazin-1-yl]-3-oxopropyl]phenoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(OC=2C(=CC=CC=2)CCC(=O)N2[C@@H](CNCC2)CC=2C=CC=CC=2)=C1 PXFWMLMFLYEOEO-RUZDIDTESA-N 0.000 claims 1
- XKZDDCKYDJLERX-HHHXNRCGSA-N n-[[2-[2-[3-[(2r)-2-benzylpiperazin-1-yl]-3-oxopropyl]-4-methylphenoxy]-5-(trifluoromethyl)phenyl]methyl]acetamide Chemical compound CC(=O)NCC1=CC(C(F)(F)F)=CC=C1OC1=CC=C(C)C=C1CCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 XKZDDCKYDJLERX-HHHXNRCGSA-N 0.000 claims 1
- BLAREQPOZKIUAB-MUUNZHRXSA-N n-[[2-[2-[3-[(2r)-2-benzylpiperazin-1-yl]-3-oxopropyl]-4-methylphenoxy]-5-methylphenyl]methyl]acetamide Chemical compound CC(=O)NCC1=CC(C)=CC=C1OC1=CC=C(C)C=C1CCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 BLAREQPOZKIUAB-MUUNZHRXSA-N 0.000 claims 1
- IXMGEEWSKFFYLH-HHHXNRCGSA-N n-[[2-[2-[3-[(2r)-2-benzylpiperazin-1-yl]-3-oxopropyl]-4-methylphenoxy]-6-methylpyridin-3-yl]methyl]acetamide Chemical compound CC(=O)NCC1=CC=C(C)N=C1OC1=CC=C(C)C=C1CCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 IXMGEEWSKFFYLH-HHHXNRCGSA-N 0.000 claims 1
- MIIRZIPMIORJIZ-MUUNZHRXSA-N n-[[2-[2-[3-[(2r)-2-benzylpiperazin-1-yl]-3-oxopropyl]-5-methylphenoxy]-5-methylphenyl]methyl]acetamide Chemical compound CC(=O)NCC1=CC(C)=CC=C1OC1=CC(C)=CC=C1CCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 MIIRZIPMIORJIZ-MUUNZHRXSA-N 0.000 claims 1
- PTFIEBFSPMNJEA-HHHXNRCGSA-N n-[[2-[2-[3-[(2r)-2-benzylpiperazin-1-yl]-3-oxopropyl]-5-methylphenoxy]-6-methylpyridin-3-yl]methyl]acetamide Chemical compound CC(=O)NCC1=CC=C(C)N=C1OC1=CC(C)=CC=C1CCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 PTFIEBFSPMNJEA-HHHXNRCGSA-N 0.000 claims 1
- IVHUZCZZYXIYHS-AREMUKBSSA-N n-[[2-[2-[3-[(2r)-2-benzylpiperazin-1-yl]-3-oxopropyl]phenoxy]-4,6-dimethylpyridin-3-yl]methyl]acetamide Chemical compound CC(=O)NCC1=C(C)C=C(C)N=C1OC1=CC=CC=C1CCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 IVHUZCZZYXIYHS-AREMUKBSSA-N 0.000 claims 1
- FPLNZOMAFVPMGB-AREMUKBSSA-N n-[[2-[2-[3-[(2r)-2-benzylpiperazin-1-yl]-3-oxopropyl]phenoxy]-5-methoxyphenyl]methyl]acetamide Chemical compound CC(=O)NCC1=CC(OC)=CC=C1OC1=CC=CC=C1CCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 FPLNZOMAFVPMGB-AREMUKBSSA-N 0.000 claims 1
- WEUWLMSICWIQTM-AREMUKBSSA-N n-[[2-[2-[3-[(2r)-2-benzylpiperazin-1-yl]-3-oxopropyl]phenoxy]phenyl]methyl]acetamide Chemical compound CC(=O)NCC1=CC=CC=C1OC1=CC=CC=C1CCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 WEUWLMSICWIQTM-AREMUKBSSA-N 0.000 claims 1
- DQGUIZZXOXJEQP-RUZDIDTESA-N n-[[2-[2-[3-[(2r)-2-benzylpiperazin-1-yl]-3-oxopropyl]phenoxy]pyridin-3-yl]methyl]acetamide Chemical compound CC(=O)NCC1=CC=CN=C1OC1=CC=CC=C1CCC(=O)N1[C@H](CC=2C=CC=CC=2)CNCC1 DQGUIZZXOXJEQP-RUZDIDTESA-N 0.000 claims 1
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- 238000007911 parenteral administration Methods 0.000 claims 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 238000007920 subcutaneous administration Methods 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- 230000000699 topical effect Effects 0.000 claims 1
- 0 CN(***I*)[C@](Cc1ccccc1)CN(*)I Chemical compound CN(***I*)[C@](Cc1ccccc1)CN(*)I 0.000 description 2
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78756406P | 2006-03-29 | 2006-03-29 | |
| PCT/US2007/064814 WO2007117961A2 (en) | 2006-03-29 | 2007-03-23 | Renin inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009534310A JP2009534310A (ja) | 2009-09-24 |
| JP2009534310A5 true JP2009534310A5 (enExample) | 2010-04-15 |
Family
ID=38529996
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009503181A Abandoned JP2009534310A (ja) | 2006-03-29 | 2007-03-23 | レニン阻害剤 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US20100210635A1 (enExample) |
| EP (1) | EP1999117A2 (enExample) |
| JP (1) | JP2009534310A (enExample) |
| WO (1) | WO2007117961A2 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090105251A1 (en) * | 2007-01-25 | 2009-04-23 | Benjamin Jones | Renin inhibitors |
| CN104031094A (zh) * | 2014-05-26 | 2014-09-10 | 上海应用技术学院 | 一种二茂铁哌嗪类衍生物及其制备方法和应用 |
| WO2019094856A1 (en) * | 2017-11-13 | 2019-05-16 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Atypical inhibitors of monoamine transporters; method of making; and use thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AUPO008396A0 (en) * | 1996-05-27 | 1996-06-20 | Fujisawa Pharmaceutical Co., Ltd. | New piperazine compounds |
| US6861424B2 (en) * | 2001-06-06 | 2005-03-01 | Schering Aktiengesellschaft | Platelet adenosine diphosphate receptor antagonists |
| CA2498272A1 (en) * | 2002-09-11 | 2004-03-25 | Merck & Co., Inc. | Piperazine urea derivatives as melanocortin-4 receptor agonists |
| US20040214832A1 (en) * | 2003-04-10 | 2004-10-28 | Cuiman Cai | Piperazine derivative renin inhibitors |
| TW200640877A (en) * | 2005-04-28 | 2006-12-01 | Actelion Pharmaceuticals Ltd | Pyrimidine derivatives |
| CA2638787A1 (en) * | 2006-02-16 | 2007-08-23 | Takeda Pharmaceutical Company Limited | Cyclic amine compound and use thereof for the prophylaxis or treatment of hypertension |
-
2007
- 2007-03-23 WO PCT/US2007/064814 patent/WO2007117961A2/en not_active Ceased
- 2007-03-23 EP EP07759273A patent/EP1999117A2/en not_active Withdrawn
- 2007-03-23 JP JP2009503181A patent/JP2009534310A/ja not_active Abandoned
- 2007-03-23 US US12/294,906 patent/US20100210635A1/en not_active Abandoned
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