NO317343B1 - Piperazinderivater og deres anvendelse som anti-inflammatoriske midler - Google Patents
Piperazinderivater og deres anvendelse som anti-inflammatoriske midler Download PDFInfo
- Publication number
- NO317343B1 NO317343B1 NO19996068A NO996068A NO317343B1 NO 317343 B1 NO317343 B1 NO 317343B1 NO 19996068 A NO19996068 A NO 19996068A NO 996068 A NO996068 A NO 996068A NO 317343 B1 NO317343 B1 NO 317343B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- carbonyl
- fluorobenzyl
- piperazine
- alkyl
- Prior art date
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- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title abstract description 12
- 229940121363 anti-inflammatory agent Drugs 0.000 title abstract description 7
- 239000002260 anti-inflammatory agent Substances 0.000 title abstract description 7
- 150000004885 piperazines Chemical class 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 288
- -1 acyl piperazine derivatives Chemical class 0.000 claims abstract description 151
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 258
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 116
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 102
- 239000000203 mixture Substances 0.000 claims description 76
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 65
- 229910052736 halogen Inorganic materials 0.000 claims description 63
- 150000002367 halogens Chemical group 0.000 claims description 63
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 55
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 52
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 49
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 47
- 125000003545 alkoxy group Chemical group 0.000 claims description 44
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 42
- 125000001424 substituent group Chemical group 0.000 claims description 42
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 39
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 125000005281 alkyl ureido group Chemical group 0.000 claims description 29
- 125000003282 alkyl amino group Chemical group 0.000 claims description 28
- 239000000460 chlorine Substances 0.000 claims description 26
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 24
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 20
- 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 claims description 16
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000005544 phthalimido group Chemical group 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000005091 alkenylcarbonylamino group Chemical group 0.000 claims description 7
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 7
- VHMATGIRIRDCHP-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[4-[(4-fluorophenyl)methyl]-3-(2-hydroxyethyl)piperazin-1-yl]ethanone Chemical compound OCCC1CN(C(=O)COC=2C=CC(Cl)=CC=2)CCN1CC1=CC=C(F)C=C1 VHMATGIRIRDCHP-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- SMRLSRWFCUILQH-CVEARBPZSA-N 2-(4-chloro-3,5-dimethoxyphenoxy)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound COC1=C(Cl)C(OC)=CC(OCC(=O)N2[C@H](CN(CC=3C=CC(F)=CC=3)[C@H](C)C2)C)=C1 SMRLSRWFCUILQH-CVEARBPZSA-N 0.000 claims description 5
- KOEWNZKNNOOJSM-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[2-ethyl-4-[(4-fluorophenyl)methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)COC=2C=CC(Cl)=CC=2)C(CC)CN1CC1=CC=C(F)C=C1 KOEWNZKNNOOJSM-UHFFFAOYSA-N 0.000 claims description 5
- POQNXYUBXCEGFG-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[4-[(4-fluorophenyl)methyl]-3-methylpiperazin-1-yl]ethanone Chemical compound CC1CN(C(=O)COC=2C=CC(Cl)=CC=2)CCN1CC1=CC=C(F)C=C1 POQNXYUBXCEGFG-UHFFFAOYSA-N 0.000 claims description 5
- PGBPKSSYIVMNRH-CVEARBPZSA-N 2-[2-(aminomethyl)-4-chlorophenoxy]-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)CN)N1CC1=CC=C(F)C=C1 PGBPKSSYIVMNRH-CVEARBPZSA-N 0.000 claims description 5
- QPIGMXAZMSKBNF-MSOLQXFVSA-N 2-[4-chloro-2-(ethylaminomethyl)phenoxy]-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound CCNCC1=CC(Cl)=CC=C1OCC(=O)N1[C@@H](C)CN(CC=2C=CC(F)=CC=2)[C@H](C)C1 QPIGMXAZMSKBNF-MSOLQXFVSA-N 0.000 claims description 5
- PPSHXTNGQPNPSD-UXHICEINSA-N 2-[4-chloro-2-(piperazin-1-ylmethyl)phenoxy]-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)CN2CCNCC2)N1CC1=CC=C(F)C=C1 PPSHXTNGQPNPSD-UXHICEINSA-N 0.000 claims description 5
- GHUDTVBWOURQRN-LSDHHAIUSA-N 5-chloro-2-[2-[(2r,5s)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]benzamide Chemical compound C([C@@H](C)N(C[C@@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)C(N)=O)N1CC1=CC=C(F)C=C1 GHUDTVBWOURQRN-LSDHHAIUSA-N 0.000 claims description 5
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 5
- UYYINTMMVIJIRI-DNVCBOLYSA-N 2-(4-chlorophenoxy)-1-[(2r,5r)-4-[(4-fluorophenyl)methyl]-5-(hydroxymethyl)-2-methylpiperazin-1-yl]ethanone Chemical compound C([C@H](N(C[C@@H]1CO)C(=O)COC=2C=CC(Cl)=CC=2)C)N1CC1=CC=C(F)C=C1 UYYINTMMVIJIRI-DNVCBOLYSA-N 0.000 claims description 4
- PAUQWKUMTWIOME-CVEARBPZSA-N 2-(4-chlorophenoxy)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C=CC(Cl)=CC=2)N1CC1=CC=C(F)C=C1 PAUQWKUMTWIOME-CVEARBPZSA-N 0.000 claims description 4
- FQMHVOZYYBVGNN-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[4-[(4-fluorophenyl)methyl]-2-(2-hydroxyethyl)piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)COC=2C=CC(Cl)=CC=2)C(CCO)CN1CC1=CC=C(F)C=C1 FQMHVOZYYBVGNN-UHFFFAOYSA-N 0.000 claims description 4
- MNFOTYUAQGGSMJ-CABCVRRESA-N 5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]benzoic acid Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)C(O)=O)N1CC1=CC=C(F)C=C1 MNFOTYUAQGGSMJ-CABCVRRESA-N 0.000 claims description 4
- TVMZRLZDWASDGW-CVEARBPZSA-N 5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]benzonitrile Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)C#N)N1CC1=CC=C(F)C=C1 TVMZRLZDWASDGW-CVEARBPZSA-N 0.000 claims description 4
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- NQJGLLOQSAIHGC-BATLZEKGSA-N 1-(2-chloroethyl)-1-[1-(4-chlorophenyl)-3-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-3-oxopropyl]urea Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)CC(N(CCCl)C(N)=O)C=2C=CC(Cl)=CC=2)N1CC1=CC=C(F)C=C1 NQJGLLOQSAIHGC-BATLZEKGSA-N 0.000 claims description 3
- NJEMIRQBWQUDOL-DLBZAZTESA-N 1-[(2r,5s)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-(3-hydroxy-5-methylphenoxy)ethanone Chemical compound C([C@@H](C)N(C[C@@H]1C)C(=O)COC=2C=C(O)C=C(C)C=2)N1CC1=CC=C(F)C=C1 NJEMIRQBWQUDOL-DLBZAZTESA-N 0.000 claims description 3
- ILILPLHOHYABCS-CALCHBBNSA-N 1-[(2r,6s)-4-[(4-fluorophenyl)methyl]-2,6-dimethylpiperazin-1-yl]-2-(3,4,5-trimethoxyphenoxy)ethanone Chemical compound COC1=C(OC)C(OC)=CC(OCC(=O)N2[C@@H](CN(CC=3C=CC(F)=CC=3)C[C@@H]2C)C)=C1 ILILPLHOHYABCS-CALCHBBNSA-N 0.000 claims description 3
- HANUAQHDFZZDNZ-SJORKVTESA-N 1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-(2-methyl-5-nitrophenoxy)ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC=C(C=2)[N+]([O-])=O)C)N1CC1=CC=C(F)C=C1 HANUAQHDFZZDNZ-SJORKVTESA-N 0.000 claims description 3
- PPDHCVDSNRPCNK-SJORKVTESA-N 1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-(3-methoxyphenoxy)ethanone Chemical compound COC1=CC=CC(OCC(=O)N2[C@H](CN(CC=3C=CC(F)=CC=3)[C@H](C)C2)C)=C1 PPDHCVDSNRPCNK-SJORKVTESA-N 0.000 claims description 3
- NOTQGAMXXQSESA-SJORKVTESA-N 1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-(3-methyl-4-nitrophenoxy)ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C=C(C)C(=CC=2)[N+]([O-])=O)N1CC1=CC=C(F)C=C1 NOTQGAMXXQSESA-SJORKVTESA-N 0.000 claims description 3
- FFMARGYVCAYQPF-CVEARBPZSA-N 1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-(3-nitrophenoxy)ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C=C(C=CC=2)[N+]([O-])=O)N1CC1=CC=C(F)C=C1 FFMARGYVCAYQPF-CVEARBPZSA-N 0.000 claims description 3
- HTSXITVXMUUAIJ-MSOLQXFVSA-N 1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-[2-(2-hydroxyethoxy)phenoxy]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC=CC=2)OCCO)N1CC1=CC=C(F)C=C1 HTSXITVXMUUAIJ-MSOLQXFVSA-N 0.000 claims description 3
- KBLJEHQKSVWETK-UHFFFAOYSA-N 1-[2-(2-azidoethyl)-4-[(4-fluorophenyl)methyl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C1=CC(F)=CC=C1CN1CC(CCN=[N+]=[N-])N(C(=O)COC=2C=CC(Cl)=CC=2)CC1 KBLJEHQKSVWETK-UHFFFAOYSA-N 0.000 claims description 3
- NLKSZJRECWDOHT-ZCQKWSGTSA-N 1-[2-(4-chlorophenyl)-4-[(2S,5R)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-4-oxobutyl]-1-(3-chloropropyl)urea Chemical compound ClC1=CC=C(C=C1)C(CC(=O)N1[C@H](CN([C@@H](C1)C)CC1=CC=C(C=C1)F)C)CN(C(=O)N)CCCCl NLKSZJRECWDOHT-ZCQKWSGTSA-N 0.000 claims description 3
- WMDUDOZEYMZACX-UHFFFAOYSA-N 1-[4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-2-(3,4,5-trimethoxyphenoxy)ethanone Chemical compound COC1=C(OC)C(OC)=CC(OCC(=O)N2C(CN(CC=3C=CC(F)=CC=3)CC2)C)=C1 WMDUDOZEYMZACX-UHFFFAOYSA-N 0.000 claims description 3
- UHMPEYATHUWEOB-UHFFFAOYSA-N 1-[4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-2-phenoxyethanone Chemical compound C1CN(C(=O)COC=2C=CC=CC=2)C(C)CN1CC1=CC=C(F)C=C1 UHMPEYATHUWEOB-UHFFFAOYSA-N 0.000 claims description 3
- MDNYDCUJOSHMFV-FTJBHMTQSA-N 1-[4-[[5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]phenyl]methyl]piperazin-1-yl]-2-phenylethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)CN2CCN(CC2)C(=O)CC=2C=CC=CC=2)N1CC1=CC=C(F)C=C1 MDNYDCUJOSHMFV-FTJBHMTQSA-N 0.000 claims description 3
- MXXOPDCCTDGOJK-SJORKVTESA-N 1-[5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]phenyl]pyrrole-2,5-dione Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)N2C(C=CC2=O)=O)N1CC1=CC=C(F)C=C1 MXXOPDCCTDGOJK-SJORKVTESA-N 0.000 claims description 3
- QFTZOCUOIZCQBZ-MOPGFXCFSA-N 2-(2-acetyl-4,5-dimethylphenoxy)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(C)=C(C)C=2)C(C)=O)N1CC1=CC=C(F)C=C1 QFTZOCUOIZCQBZ-MOPGFXCFSA-N 0.000 claims description 3
- UMEWDZGRJUGUFT-CVEARBPZSA-N 2-(2-acetyl-4-chlorophenoxy)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)C(C)=O)N1CC1=CC=C(F)C=C1 UMEWDZGRJUGUFT-CVEARBPZSA-N 0.000 claims description 3
- HMZIGHJMFPRRJM-SJORKVTESA-N 2-(2-acetyl-4-methoxyphenoxy)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound CC(=O)C1=CC(OC)=CC=C1OCC(=O)N1[C@@H](C)CN(CC=2C=CC(F)=CC=2)[C@H](C)C1 HMZIGHJMFPRRJM-SJORKVTESA-N 0.000 claims description 3
- OYYDVFFJVPZOGU-MSOLQXFVSA-N 2-(2-acetyl-4-methylphenoxy)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(C)=CC=2)C(C)=O)N1CC1=CC=C(F)C=C1 OYYDVFFJVPZOGU-MSOLQXFVSA-N 0.000 claims description 3
- YXSDFJMJUGHSMK-SJORKVTESA-N 2-(2-acetyl-5-methoxyphenoxy)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound COC1=CC=C(C(C)=O)C(OCC(=O)N2[C@H](CN(CC=3C=CC(F)=CC=3)[C@H](C)C2)C)=C1 YXSDFJMJUGHSMK-SJORKVTESA-N 0.000 claims description 3
- MMUYKPOLYWHQLP-CABCVRRESA-N 2-(2-amino-4-chlorophenoxy)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)N)N1CC1=CC=C(F)C=C1 MMUYKPOLYWHQLP-CABCVRRESA-N 0.000 claims description 3
- PMFDTQBSJLHLIU-UHFFFAOYSA-N 2-(2-amino-4-chlorophenoxy)-1-[4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]ethanone Chemical compound C1CN(C(=O)COC=2C(=CC(Cl)=CC=2)N)C(C)CN1CC1=CC=C(F)C=C1 PMFDTQBSJLHLIU-UHFFFAOYSA-N 0.000 claims description 3
- PRLZXRDAPUUSMJ-SJORKVTESA-N 2-(2-amino-4-methylphenoxy)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(C)=CC=2)N)N1CC1=CC=C(F)C=C1 PRLZXRDAPUUSMJ-SJORKVTESA-N 0.000 claims description 3
- BSOXIWBRLWTRAN-CABCVRRESA-N 2-(2-amino-5-nitrophenoxy)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC=C(C=2)[N+]([O-])=O)N)N1CC1=CC=C(F)C=C1 BSOXIWBRLWTRAN-CABCVRRESA-N 0.000 claims description 3
- DUPYWSYBADQWMU-CVEARBPZSA-N 2-(2-aminophenoxy)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC=CC=2)N)N1CC1=CC=C(F)C=C1 DUPYWSYBADQWMU-CVEARBPZSA-N 0.000 claims description 3
- PTIGVIAHTZQBRM-CABCVRRESA-N 2-(3-chloro-4-fluorophenoxy)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C=C(Cl)C(F)=CC=2)N1CC1=CC=C(F)C=C1 PTIGVIAHTZQBRM-CABCVRRESA-N 0.000 claims description 3
- NGMRQQZDOJGABT-CABCVRRESA-N 2-(4-amino-3-nitrophenoxy)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C=C(C(N)=CC=2)[N+]([O-])=O)N1CC1=CC=C(F)C=C1 NGMRQQZDOJGABT-CABCVRRESA-N 0.000 claims description 3
- IBAYFIKREMDYKM-SJORKVTESA-N 2-(4-chloro-2-methylphenoxy)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)C)N1CC1=CC=C(F)C=C1 IBAYFIKREMDYKM-SJORKVTESA-N 0.000 claims description 3
- RKIURRQAUDEMOF-UHFFFAOYSA-N 2-(4-chloro-3-nitrophenoxy)-1-[4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]ethanone Chemical compound C1CN(C(=O)COC=2C=C(C(Cl)=CC=2)[N+]([O-])=O)C(C)CN1CC1=CC=C(F)C=C1 RKIURRQAUDEMOF-UHFFFAOYSA-N 0.000 claims description 3
- HWWATAKTEAWFDN-CVEARBPZSA-N 2-(4-chloroanilino)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)CNC=2C=CC(Cl)=CC=2)N1CC1=CC=C(F)C=C1 HWWATAKTEAWFDN-CVEARBPZSA-N 0.000 claims description 3
- ROWPYOBDGRMKET-UHFFFAOYSA-N 2-(4-chloroanilino)-1-[4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]ethanone Chemical compound C1CN(C(=O)CNC=2C=CC(Cl)=CC=2)C(C)CN1CC1=CC=C(F)C=C1 ROWPYOBDGRMKET-UHFFFAOYSA-N 0.000 claims description 3
- HQLNLEFFXBXJIW-OAHLLOKOSA-N 2-(4-chlorophenoxy)-1-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]ethanone Chemical compound C([C@H](N(CC1)C(=O)COC=2C=CC(Cl)=CC=2)C)N1CC1=CC=C(F)C=C1 HQLNLEFFXBXJIW-OAHLLOKOSA-N 0.000 claims description 3
- ADGBGESQLGKQMG-HXUWFJFHSA-N 2-(4-chlorophenoxy)-1-[(2r)-4-[(4-fluorophenyl)methyl]-2-propylpiperazin-1-yl]ethanone Chemical compound C([C@H](N(CC1)C(=O)COC=2C=CC(Cl)=CC=2)CCC)N1CC1=CC=C(F)C=C1 ADGBGESQLGKQMG-HXUWFJFHSA-N 0.000 claims description 3
- JZSWMZLRVSDUDU-UTKZUKDTSA-N 2-(4-chlorophenoxy)-1-[(2r,5r)-4-[(4-fluorophenyl)methyl]-2-methyl-5-(1,2,4-triazol-1-ylmethyl)piperazin-1-yl]ethanone Chemical compound C([C@H](N(C[C@@H]1CN2N=CN=C2)C(=O)COC=2C=CC(Cl)=CC=2)C)N1CC1=CC=C(F)C=C1 JZSWMZLRVSDUDU-UTKZUKDTSA-N 0.000 claims description 3
- DBZWXRLAWVPNPL-DNVCBOLYSA-N 2-(4-chlorophenoxy)-1-[(2r,5r)-4-[(4-fluorophenyl)methyl]-2-methyl-5-(2h-tetrazol-5-ylmethyl)piperazin-1-yl]ethanone Chemical compound C([C@H](N(C[C@H]1CC=2NN=NN=2)C(=O)COC=2C=CC(Cl)=CC=2)C)N1CC1=CC=C(F)C=C1 DBZWXRLAWVPNPL-DNVCBOLYSA-N 0.000 claims description 3
- UXYFXAJJVLCSEE-QFQXNSOFSA-N 2-(4-chlorophenoxy)-1-[(2r,5r)-4-[(4-fluorophenyl)methyl]-2-methyl-5-(phenylmethoxymethyl)piperazin-1-yl]ethanone Chemical compound C([C@H](N(C[C@@H]1COCC=2C=CC=CC=2)C(=O)COC=2C=CC(Cl)=CC=2)C)N1CC1=CC=C(F)C=C1 UXYFXAJJVLCSEE-QFQXNSOFSA-N 0.000 claims description 3
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- VZOXJRVVLAECMX-OXQOHEQNSA-N 2-(4-chlorophenoxy)-1-[(2r,5r)-4-[(4-fluorophenyl)methyl]-5-(methoxymethyl)-2-methylpiperazin-1-yl]ethanone Chemical compound C([C@@H](C)N(C[C@@H]1COC)C(=O)COC=2C=CC(Cl)=CC=2)N1CC1=CC=C(F)C=C1 VZOXJRVVLAECMX-OXQOHEQNSA-N 0.000 claims description 3
- PAUQWKUMTWIOME-JKSUJKDBSA-N 2-(4-chlorophenoxy)-1-[(2r,5s)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@@H](C)N(C[C@@H]1C)C(=O)COC=2C=CC(Cl)=CC=2)N1CC1=CC=C(F)C=C1 PAUQWKUMTWIOME-JKSUJKDBSA-N 0.000 claims description 3
- RBIXDGADUXIOOC-OXJNMPFZSA-N 2-(4-chlorophenoxy)-1-[(2r,5s)-4-[(4-fluorophenyl)methyl]-2-(2-hydroxyethyl)-5-methylpiperazin-1-yl]ethanone Chemical compound C([C@@H](CCO)N(C[C@@H]1C)C(=O)COC=2C=CC(Cl)=CC=2)N1CC1=CC=C(F)C=C1 RBIXDGADUXIOOC-OXJNMPFZSA-N 0.000 claims description 3
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- CLNSXWXGALTRGZ-CVEARBPZSA-N 2-(5-chloro-2-methoxyphenoxy)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound COC1=CC=C(Cl)C=C1OCC(=O)N1[C@@H](C)CN(CC=2C=CC(F)=CC=2)[C@H](C)C1 CLNSXWXGALTRGZ-CVEARBPZSA-N 0.000 claims description 3
- GVMAYQBKXXWFRI-CVEARBPZSA-N 2-(carbamoylamino)-n-[5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]phenyl]acetamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)NC(=O)CNC(N)=O)N1CC1=CC=C(F)C=C1 GVMAYQBKXXWFRI-CVEARBPZSA-N 0.000 claims description 3
- OKMRIFDDFUDCHL-UZLBHIALSA-N 2-[(2s,5r)-4-[2-(4-chlorophenoxy)acetyl]-1-[(4-fluorophenyl)methyl]-5-methylpiperazin-2-yl]acetonitrile Chemical compound C([C@H](N(C[C@@H]1CC#N)C(=O)COC=2C=CC(Cl)=CC=2)C)N1CC1=CC=C(F)C=C1 OKMRIFDDFUDCHL-UZLBHIALSA-N 0.000 claims description 3
- PEJBGFVJIARBLH-RTWAWAEBSA-N 2-[2-(anilinomethyl)-4-chlorophenoxy]-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)CNC=2C=CC=CC=2)N1CC1=CC=C(F)C=C1 PEJBGFVJIARBLH-RTWAWAEBSA-N 0.000 claims description 3
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- SWAZJQQUYSYYBW-MSOLQXFVSA-N 2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]-n-(2-hydroxyethyl)benzamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC=CC=2)C(=O)NCCO)N1CC1=CC=C(F)C=C1 SWAZJQQUYSYYBW-MSOLQXFVSA-N 0.000 claims description 3
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- GQMDZOJEHDMYSW-LFPSWIHMSA-N 2-[4-chloro-2-(1-imidazol-1-ylethyl)phenoxy]-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound N1([C@H](C)CN([C@H](C1)C)C(=O)COC1=CC=C(Cl)C=C1C(C)N1C=NC=C1)CC1=CC=C(F)C=C1 GQMDZOJEHDMYSW-LFPSWIHMSA-N 0.000 claims description 3
- XAWYVEUJMWOPLA-MOPGFXCFSA-N 2-[4-chloro-2-(diethylamino)phenoxy]-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound CCN(CC)C1=CC(Cl)=CC=C1OCC(=O)N1[C@@H](C)CN(CC=2C=CC(F)=CC=2)[C@H](C)C1 XAWYVEUJMWOPLA-MOPGFXCFSA-N 0.000 claims description 3
- KALJELAGERDQKZ-UXHICEINSA-N 2-[4-chloro-2-(diethylaminomethyl)phenoxy]-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound CCN(CC)CC1=CC(Cl)=CC=C1OCC(=O)N1[C@@H](C)CN(CC=2C=CC(F)=CC=2)[C@H](C)C1 KALJELAGERDQKZ-UXHICEINSA-N 0.000 claims description 3
- MREYLDAZJNPDCT-MOPGFXCFSA-N 2-[4-chloro-2-(imidazol-1-ylmethyl)phenoxy]-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)CN2C=NC=C2)N1CC1=CC=C(F)C=C1 MREYLDAZJNPDCT-MOPGFXCFSA-N 0.000 claims description 3
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- DXZQBSFTEQBERC-UXHICEINSA-N 2-[4-chloro-2-(morpholin-4-ylmethyl)phenoxy]-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)CN2CCOCC2)N1CC1=CC=C(F)C=C1 DXZQBSFTEQBERC-UXHICEINSA-N 0.000 claims description 3
- HJSJCIWPZCDSFV-UHFFFAOYSA-N 2-[4-chloro-2-(morpholin-4-ylmethyl)phenoxy]-1-[4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]ethanone Chemical compound C1CN(C(=O)COC=2C(=CC(Cl)=CC=2)CN2CCOCC2)C(C)CN1CC1=CC=C(F)C=C1 HJSJCIWPZCDSFV-UHFFFAOYSA-N 0.000 claims description 3
- MPGIOPZIGAYCJA-HUSUDBNBSA-N 2-[4-chloro-2-(pentan-2-ylamino)phenoxy]-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound CCCC(C)NC1=CC(Cl)=CC=C1OCC(=O)N1[C@@H](C)CN(CC=2C=CC(F)=CC=2)[C@H](C)C1 MPGIOPZIGAYCJA-HUSUDBNBSA-N 0.000 claims description 3
- CURJICFKDXJFII-MSOLQXFVSA-N 2-[4-chloro-2-(triazol-1-ylmethyl)phenoxy]-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)CN2N=NC=C2)N1CC1=CC=C(F)C=C1 CURJICFKDXJFII-MSOLQXFVSA-N 0.000 claims description 3
- VKUOLMHVCZBJPL-MSOLQXFVSA-N 2-[4-chloro-2-[(1,3-oxazol-2-ylamino)methyl]phenoxy]-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)CNC=2OC=CN=2)N1CC1=CC=C(F)C=C1 VKUOLMHVCZBJPL-MSOLQXFVSA-N 0.000 claims description 3
- QZCBSKJPWFFFSO-RTWAWAEBSA-N 2-[4-chloro-2-[(4-methylpiperazin-1-yl)methyl]phenoxy]-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)CN2CCN(C)CC2)N1CC1=CC=C(F)C=C1 QZCBSKJPWFFFSO-RTWAWAEBSA-N 0.000 claims description 3
- FMZDCRVVOQNCOP-MSOLQXFVSA-N 2-[4-chloro-2-[(cyclopropylamino)methyl]phenoxy]-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)CNC2CC2)N1CC1=CC=C(F)C=C1 FMZDCRVVOQNCOP-MSOLQXFVSA-N 0.000 claims description 3
- JHQLLJJURFOGJZ-MOPGFXCFSA-N 2-[4-chloro-2-[(cyclopropylmethylamino)methyl]phenoxy]-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)CNCC2CC2)N1CC1=CC=C(F)C=C1 JHQLLJJURFOGJZ-MOPGFXCFSA-N 0.000 claims description 3
- VJKDAKLSTRJMLR-MSOLQXFVSA-N 2-[4-chloro-2-[(dimethylamino)methyl]phenoxy]-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)CN(C)C)N1CC1=CC=C(F)C=C1 VJKDAKLSTRJMLR-MSOLQXFVSA-N 0.000 claims description 3
- WRQIECRISNJLQO-YTYFACEESA-N 2-[4-chloro-2-[1-(dimethylamino)ethyl]phenoxy]-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound CN(C)C(C)C1=CC(Cl)=CC=C1OCC(=O)N1[C@@H](C)CN(CC=2C=CC(F)=CC=2)[C@H](C)C1 WRQIECRISNJLQO-YTYFACEESA-N 0.000 claims description 3
- AYWDDNDEGCQCRD-LFPSWIHMSA-N 2-[4-chloro-2-[1-[ethyl(methyl)amino]ethyl]phenoxy]-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound CCN(C)C(C)C1=CC(Cl)=CC=C1OCC(=O)N1[C@@H](C)CN(CC=2C=CC(F)=CC=2)[C@H](C)C1 AYWDDNDEGCQCRD-LFPSWIHMSA-N 0.000 claims description 3
- AQOHDFFVGYUOEZ-IHHKOXMGSA-N 2-[4-chloro-2-[2-(methylamino)-1-methylsulfonylethyl]phenoxy]-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound CNCC(S(C)(=O)=O)C1=CC(Cl)=CC=C1OCC(=O)N1[C@@H](C)CN(CC=2C=CC(F)=CC=2)[C@H](C)C1 AQOHDFFVGYUOEZ-IHHKOXMGSA-N 0.000 claims description 3
- SONRDGCRZBJREB-JKSUJKDBSA-N 2-[4-chloro-3-(hydroxymethyl)phenoxy]-1-[(2r,5s)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@@H](C)N(C[C@@H]1C)C(=O)COC=2C=C(CO)C(Cl)=CC=2)N1CC1=CC=C(F)C=C1 SONRDGCRZBJREB-JKSUJKDBSA-N 0.000 claims description 3
- SBYXRUJKWQYLSM-MOPGFXCFSA-N 2-[5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]phenyl]isoindole-1,3-dione Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)N2C(C3=CC=CC=C3C2=O)=O)N1CC1=CC=C(F)C=C1 SBYXRUJKWQYLSM-MOPGFXCFSA-N 0.000 claims description 3
- OGCRPMAWSHREKZ-SJORKVTESA-N 2-[carbamoyl(methyl)amino]-n-[5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]phenyl]acetamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)NC(=O)CN(C)C(N)=O)N1CC1=CC=C(F)C=C1 OGCRPMAWSHREKZ-SJORKVTESA-N 0.000 claims description 3
- GVIKXLKPTUHXED-MSOLQXFVSA-N 2-hydroxyethyl 2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]benzoate Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC=CC=2)C(=O)OCCO)N1CC1=CC=C(F)C=C1 GVIKXLKPTUHXED-MSOLQXFVSA-N 0.000 claims description 3
- FTPKKPFWSWQONK-SJORKVTESA-N 3-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]benzonitrile Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C=C(C=CC=2)C#N)N1CC1=CC=C(F)C=C1 FTPKKPFWSWQONK-SJORKVTESA-N 0.000 claims description 3
- LOUIQIRIQFRHAP-IHHKOXMGSA-N 3-[5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]phenyl]-4-(methylamino)butan-2-one Chemical compound CNCC(C(C)=O)C1=CC(Cl)=CC=C1OCC(=O)N1[C@@H](C)CN(CC=2C=CC(F)=CC=2)[C@H](C)C1 LOUIQIRIQFRHAP-IHHKOXMGSA-N 0.000 claims description 3
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 3
- BGUMERZVCOCUKQ-CVEARBPZSA-N 5-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]-2-nitrobenzaldehyde Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C=C(C=O)C(=CC=2)[N+]([O-])=O)N1CC1=CC=C(F)C=C1 BGUMERZVCOCUKQ-CVEARBPZSA-N 0.000 claims description 3
- VVOKHLLJTWHERE-CVEARBPZSA-N 5-acetyl-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]benzamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(=CC=2)C(C)=O)C(N)=O)N1CC1=CC=C(F)C=C1 VVOKHLLJTWHERE-CVEARBPZSA-N 0.000 claims description 3
- XGOARMHKUKEIMT-CVEARBPZSA-N 5-bromo-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]benzaldehyde Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Br)=CC=2)C=O)N1CC1=CC=C(F)C=C1 XGOARMHKUKEIMT-CVEARBPZSA-N 0.000 claims description 3
- HBWNYZOMZGDQPN-OAHLLOKOSA-N 5-chloro-2-[2-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-2-oxoethoxy]benzaldehyde Chemical compound C([C@H](N(CC1)C(=O)COC=2C(=CC(Cl)=CC=2)C=O)C)N1CC1=CC=C(F)C=C1 HBWNYZOMZGDQPN-OAHLLOKOSA-N 0.000 claims description 3
- MNVXSJCMBNIGEM-CQSZACIVSA-N 5-chloro-2-[2-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-2-oxoethoxy]benzamide Chemical compound C([C@H](N(CC1)C(=O)COC=2C(=CC(Cl)=CC=2)C(N)=O)C)N1CC1=CC=C(F)C=C1 MNVXSJCMBNIGEM-CQSZACIVSA-N 0.000 claims description 3
- BBSLUNNJFYBMTP-JKSUJKDBSA-N 5-chloro-2-[2-[(2r,5s)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]benzaldehyde Chemical compound C([C@@H](C)N(C[C@@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)C=O)N1CC1=CC=C(F)C=C1 BBSLUNNJFYBMTP-JKSUJKDBSA-N 0.000 claims description 3
- NRDGKRYQNVRZJL-CABCVRRESA-N 5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]-n'-hydroxybenzenecarboximidamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)C(=N)NO)N1CC1=CC=C(F)C=C1 NRDGKRYQNVRZJL-CABCVRRESA-N 0.000 claims description 3
- BBSLUNNJFYBMTP-CVEARBPZSA-N 5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]benzaldehyde Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)C=O)N1CC1=CC=C(F)C=C1 BBSLUNNJFYBMTP-CVEARBPZSA-N 0.000 claims description 3
- MNVXSJCMBNIGEM-UHFFFAOYSA-N 5-chloro-2-[2-[4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-2-oxoethoxy]benzamide Chemical compound C1CN(C(=O)COC=2C(=CC(Cl)=CC=2)C(N)=O)C(C)CN1CC1=CC=C(F)C=C1 MNVXSJCMBNIGEM-UHFFFAOYSA-N 0.000 claims description 3
- YBTMNUXCBVWSCX-UHFFFAOYSA-N 5-chloro-2-[[2-[4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-2-oxoethyl]amino]benzamide Chemical compound C1CN(C(=O)CNC=2C(=CC(Cl)=CC=2)C(N)=O)C(C)CN1CC1=CC=C(F)C=C1 YBTMNUXCBVWSCX-UHFFFAOYSA-N 0.000 claims description 3
- NYWUDDNQNSJFDO-SJORKVTESA-N 7-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]chromen-2-one Chemical group C([C@H](C)N(C[C@H]1C)C(=O)COC=2C=C3OC(=O)C=CC3=CC=2)N1CC1=CC=C(F)C=C1 NYWUDDNQNSJFDO-SJORKVTESA-N 0.000 claims description 3
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 3
- INPFALVFXCHPCN-ZQIYAJFXSA-N [1-(4-chlorophenyl)-3-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-3-oxopropyl]urea Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)CC(NC(N)=O)C=2C=CC(Cl)=CC=2)N1CC1=CC=C(F)C=C1 INPFALVFXCHPCN-ZQIYAJFXSA-N 0.000 claims description 3
- AHRMKPWSQVUKNA-LIHHCBPRSA-N [2-(4-chlorophenyl)-4-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-4-oxobutyl]urea Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)CC(CNC(N)=O)C=2C=CC(Cl)=CC=2)N1CC1=CC=C(F)C=C1 AHRMKPWSQVUKNA-LIHHCBPRSA-N 0.000 claims description 3
- XQYASZNUFDVMFH-CQSZACIVSA-N [5-chloro-2-[2-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-2-oxoethoxy]phenyl]urea Chemical compound C([C@H](N(CC1)C(=O)COC=2C(=CC(Cl)=CC=2)NC(N)=O)C)N1CC1=CC=C(F)C=C1 XQYASZNUFDVMFH-CQSZACIVSA-N 0.000 claims description 3
- NIVZHDPWEOPUAK-LSDHHAIUSA-N [5-chloro-2-[2-[(2r,5s)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]phenyl]urea Chemical compound C([C@@H](C)N(C[C@@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)NC(N)=O)N1CC1=CC=C(F)C=C1 NIVZHDPWEOPUAK-LSDHHAIUSA-N 0.000 claims description 3
- XQYASZNUFDVMFH-AWEZNQCLSA-N [5-chloro-2-[2-[(2s)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-2-oxoethoxy]phenyl]urea Chemical compound C([C@@H](N(CC1)C(=O)COC=2C(=CC(Cl)=CC=2)NC(N)=O)C)N1CC1=CC=C(F)C=C1 XQYASZNUFDVMFH-AWEZNQCLSA-N 0.000 claims description 3
- CLTNACSCOXCXEB-CVEARBPZSA-N [5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]phenyl]methylurea Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)CNC(N)=O)N1CC1=CC=C(F)C=C1 CLTNACSCOXCXEB-CVEARBPZSA-N 0.000 claims description 3
- NIVZHDPWEOPUAK-CABCVRRESA-N [5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]phenyl]urea Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)NC(N)=O)N1CC1=CC=C(F)C=C1 NIVZHDPWEOPUAK-CABCVRRESA-N 0.000 claims description 3
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- WLJSCSKFBQCIKC-SJORKVTESA-N methyl 2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]-4-methoxybenzoate Chemical compound COC(=O)C1=CC=C(OC)C=C1OCC(=O)N1[C@@H](C)CN(CC=2C=CC(F)=CC=2)[C@H](C)C1 WLJSCSKFBQCIKC-SJORKVTESA-N 0.000 claims description 3
- HOBHUAOJUKEQST-SJORKVTESA-N methyl 2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]benzoate Chemical compound COC(=O)C1=CC=CC=C1OCC(=O)N1[C@@H](C)CN(CC=2C=CC(F)=CC=2)[C@H](C)C1 HOBHUAOJUKEQST-SJORKVTESA-N 0.000 claims description 3
- QRTDSDITRSAIQH-MSOLQXFVSA-N methyl 4-[5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]anilino]-4-oxobutanoate Chemical compound COC(=O)CCC(=O)NC1=CC(Cl)=CC=C1OCC(=O)N1[C@@H](C)CN(CC=2C=CC(F)=CC=2)[C@H](C)C1 QRTDSDITRSAIQH-MSOLQXFVSA-N 0.000 claims description 3
- UZEARUXBKBDPOX-CVEARBPZSA-N methyl 5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]benzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1OCC(=O)N1[C@@H](C)CN(CC=2C=CC(F)=CC=2)[C@H](C)C1 UZEARUXBKBDPOX-CVEARBPZSA-N 0.000 claims description 3
- ALFVJAPREKBBDD-UHFFFAOYSA-N methyl 5-chloro-2-[2-[4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-2-oxoethoxy]benzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1OCC(=O)N1C(C)CN(CC=2C=CC(F)=CC=2)CC1 ALFVJAPREKBBDD-UHFFFAOYSA-N 0.000 claims description 3
- LDTGCHHJRLKARY-SJORKVTESA-N n-(2-aminoethyl)-5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]benzamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)C(=O)NCCN)N1CC1=CC=C(F)C=C1 LDTGCHHJRLKARY-SJORKVTESA-N 0.000 claims description 3
- CIDBCCVYALUWKL-MOPGFXCFSA-N n-(4-carbamoylphenyl)-5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]benzamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(=CC=2)C(N)=O)N1CC1=CC=C(F)C=C1 CIDBCCVYALUWKL-MOPGFXCFSA-N 0.000 claims description 3
- ROUYCNLLYLRAQM-VSVPBVKKSA-N n-[1-(4-chlorophenyl)-3-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-3-oxopropyl]-2,4-dinitrobenzenesulfonamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)CC(NS(=O)(=O)C=2C(=CC(=CC=2)[N+]([O-])=O)[N+]([O-])=O)C=2C=CC(Cl)=CC=2)N1CC1=CC=C(F)C=C1 ROUYCNLLYLRAQM-VSVPBVKKSA-N 0.000 claims description 3
- BMCHVRSQGSGPMY-QQRJRCLASA-N n-[1-(4-chlorophenyl)-3-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-3-oxopropyl]-2-(4-methoxyphenyl)acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)NC(C=1C=CC(Cl)=CC=1)CC(=O)N1[C@@H](C)CN(CC=2C=CC(F)=CC=2)[C@H](C)C1 BMCHVRSQGSGPMY-QQRJRCLASA-N 0.000 claims description 3
- UXXRBHPOCIHLAA-YJIDZIMYSA-N n-[1-(4-chlorophenyl)-3-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-3-oxopropyl]-2-nitrobenzamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)CC(NC(=O)C=2C(=CC=CC=2)[N+]([O-])=O)C=2C=CC(Cl)=CC=2)N1CC1=CC=C(F)C=C1 UXXRBHPOCIHLAA-YJIDZIMYSA-N 0.000 claims description 3
- VGUUUCGKZWIORD-YJIDZIMYSA-N n-[1-(4-chlorophenyl)-3-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-3-oxopropyl]-3-cyclopropylpropanamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)CC(NC(=O)CCC2CC2)C=2C=CC(Cl)=CC=2)N1CC1=CC=C(F)C=C1 VGUUUCGKZWIORD-YJIDZIMYSA-N 0.000 claims description 3
- UCIJNLVOXVWTOC-RQJVYDMZSA-N n-[1-(4-chlorophenyl)-3-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-3-oxopropyl]acetamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)CC(NC(C)=O)C=2C=CC(Cl)=CC=2)N1CC1=CC=C(F)C=C1 UCIJNLVOXVWTOC-RQJVYDMZSA-N 0.000 claims description 3
- UNHGZQBFJDHZJI-IHHKOXMGSA-N n-[1-(4-chlorophenyl)-3-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-3-oxopropyl]cyclopropanecarboxamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)CC(NC(=O)C2CC2)C=2C=CC(Cl)=CC=2)N1CC1=CC=C(F)C=C1 UNHGZQBFJDHZJI-IHHKOXMGSA-N 0.000 claims description 3
- SMAQUOGQQBGJGR-KDPSSXBDSA-N n-[1-(4-chlorophenyl)-3-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-3-oxopropyl]methanesulfonamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)CC(NS(C)(=O)=O)C=2C=CC(Cl)=CC=2)N1CC1=CC=C(F)C=C1 SMAQUOGQQBGJGR-KDPSSXBDSA-N 0.000 claims description 3
- TUBNYRKJQRVZQE-HVHHGIHYSA-N n-[2-(4-chlorophenyl)-4-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-4-oxobutyl]acetamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)CC(CNC(C)=O)C=2C=CC(Cl)=CC=2)N1CC1=CC=C(F)C=C1 TUBNYRKJQRVZQE-HVHHGIHYSA-N 0.000 claims description 3
- MZEADHQKBRSTDI-GJAAFAAWSA-N n-[2-(4-chlorophenyl)-4-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-4-oxobutyl]cyclopentanecarboxamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)CC(CNC(=O)C2CCCC2)C=2C=CC(Cl)=CC=2)N1CC1=CC=C(F)C=C1 MZEADHQKBRSTDI-GJAAFAAWSA-N 0.000 claims description 3
- TYODPDHNFBMJBI-IZKAZRHKSA-N n-[2-(4-chlorophenyl)-4-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-4-oxobutyl]methanesulfonamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)CC(CNS(C)(=O)=O)C=2C=CC(Cl)=CC=2)N1CC1=CC=C(F)C=C1 TYODPDHNFBMJBI-IZKAZRHKSA-N 0.000 claims description 3
- AHXWUOJXZMPWCJ-JBAPTLGWSA-N n-[2-(4-chlorophenyl)-4-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-4-oxobutyl]morpholine-4-carboxamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)CC(CNC(=O)N2CCOCC2)C=2C=CC(Cl)=CC=2)N1CC1=CC=C(F)C=C1 AHXWUOJXZMPWCJ-JBAPTLGWSA-N 0.000 claims description 3
- LILUKMWDPYRJQC-SJORKVTESA-N n-[5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]phenyl]-2-methoxyacetamide Chemical compound COCC(=O)NC1=CC(Cl)=CC=C1OCC(=O)N1[C@@H](C)CN(CC=2C=CC(F)=CC=2)[C@H](C)C1 LILUKMWDPYRJQC-SJORKVTESA-N 0.000 claims description 3
- LRSJENLSGSVZCP-CVEARBPZSA-N n-[5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]phenyl]acetamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)NC(C)=O)N1CC1=CC=C(F)C=C1 LRSJENLSGSVZCP-CVEARBPZSA-N 0.000 claims description 3
- ZQBLLKCRNYQFTQ-UXHICEINSA-N n-[5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]phenyl]benzamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)NC(=O)C=2C=CC=CC=2)N1CC1=CC=C(F)C=C1 ZQBLLKCRNYQFTQ-UXHICEINSA-N 0.000 claims description 3
- BXQUURBTEUMRPJ-SJORKVTESA-N n-[5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]phenyl]cyclopropanecarboxamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)NC(=O)C2CC2)N1CC1=CC=C(F)C=C1 BXQUURBTEUMRPJ-SJORKVTESA-N 0.000 claims description 3
- TXALKMNLNMSWIR-MSOLQXFVSA-N n-[5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]phenyl]furan-2-carboxamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)NC(=O)C=2OC=CC=2)N1CC1=CC=C(F)C=C1 TXALKMNLNMSWIR-MSOLQXFVSA-N 0.000 claims description 3
- RIKOCIWUJNRMQZ-CVEARBPZSA-N n-[5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]phenyl]methanesulfonamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)NS(C)(=O)=O)N1CC1=CC=C(F)C=C1 RIKOCIWUJNRMQZ-CVEARBPZSA-N 0.000 claims description 3
- OJAWLAKCVZZXTG-SJORKVTESA-N n-[5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]phenyl]propanamide Chemical compound CCC(=O)NC1=CC(Cl)=CC=C1OCC(=O)N1[C@@H](C)CN(CC=2C=CC(F)=CC=2)[C@H](C)C1 OJAWLAKCVZZXTG-SJORKVTESA-N 0.000 claims description 3
- AGBFQMDEUSMFQF-UHFFFAOYSA-N n-[5-chloro-2-[2-[4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]-2-oxoethoxy]phenyl]acetamide Chemical compound C1CN(C(=O)COC=2C(=CC(Cl)=CC=2)NC(C)=O)C(C)CN1CC1=CC=C(F)C=C1 AGBFQMDEUSMFQF-UHFFFAOYSA-N 0.000 claims description 3
- SJQMAZOEKMQCER-UXHICEINSA-N n-[[5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]phenyl]methyl]-2-iodobenzamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)CNC(=O)C=2C(=CC=CC=2)I)N1CC1=CC=C(F)C=C1 SJQMAZOEKMQCER-UXHICEINSA-N 0.000 claims description 3
- YKKQPYFWYIAICA-UXHICEINSA-N n-[[5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]phenyl]methyl]-3-fluorobenzamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)CNC(=O)C=2C=C(F)C=CC=2)N1CC1=CC=C(F)C=C1 YKKQPYFWYIAICA-UXHICEINSA-N 0.000 claims description 3
- MHUIABAOFUMEJJ-SJORKVTESA-N n-[[5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]phenyl]methyl]acetamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)CNC(C)=O)N1CC1=CC=C(F)C=C1 MHUIABAOFUMEJJ-SJORKVTESA-N 0.000 claims description 3
- ITWNKJOZWFGURS-ZCQKWSGTSA-N tert-butyl n-[2-(4-chlorophenyl)-4-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-4-oxobutyl]carbamate Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)CC(CNC(=O)OC(C)(C)C)C=2C=CC(Cl)=CC=2)N1CC1=CC=C(F)C=C1 ITWNKJOZWFGURS-ZCQKWSGTSA-N 0.000 claims description 3
- WTUWYVFKYVJHAL-IKGGRYGDSA-N (2s)-2-amino-n-[5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]phenyl]propanamide Chemical compound C[C@H](N)C(=O)NC1=CC(Cl)=CC=C1OCC(=O)N1[C@@H](C)CN(CC=2C=CC(F)=CC=2)[C@H](C)C1 WTUWYVFKYVJHAL-IKGGRYGDSA-N 0.000 claims description 2
- ABGBFRAKYHAVJU-CVEARBPZSA-N 1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-(2-methoxy-5-nitrophenoxy)ethanone Chemical compound COC1=CC=C([N+]([O-])=O)C=C1OCC(=O)N1[C@@H](C)CN(CC=2C=CC(F)=CC=2)[C@H](C)C1 ABGBFRAKYHAVJU-CVEARBPZSA-N 0.000 claims description 2
- QQEISCVKADSFQN-MSOLQXFVSA-N 1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-(2-methylphenoxy)ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC=CC=2)C)N1CC1=CC=C(F)C=C1 QQEISCVKADSFQN-MSOLQXFVSA-N 0.000 claims description 2
- NJSJEKWWVBEXDN-SJORKVTESA-N 1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-[2-(hydroxymethyl)phenoxy]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC=CC=2)CO)N1CC1=CC=C(F)C=C1 NJSJEKWWVBEXDN-SJORKVTESA-N 0.000 claims description 2
- NHDLZVOORQSYDR-DKPCLATOSA-N 1-[2-(4-chlorophenyl)-4-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-4-oxobutyl]-3-ethylurea Chemical compound N1([C@H](C)CN([C@H](C1)C)C(=O)CC(CNC(=O)NCC)C=1C=CC(Cl)=CC=1)CC1=CC=C(F)C=C1 NHDLZVOORQSYDR-DKPCLATOSA-N 0.000 claims description 2
- ONVGAPYYLNXVRC-UHFFFAOYSA-N 1-[2-ethyl-4-[(4-fluorophenyl)methyl]piperazin-1-yl]-2-phenoxyethanone Chemical compound C1CN(C(=O)COC=2C=CC=CC=2)C(CC)CN1CC1=CC=C(F)C=C1 ONVGAPYYLNXVRC-UHFFFAOYSA-N 0.000 claims description 2
- RXVCXZLAPQWSTQ-UHFFFAOYSA-N 1-[4-[2-(4-chlorophenoxy)acetyl]-1-[(4-fluorophenyl)methyl]piperazin-2-yl]propan-2-one Chemical compound CC(=O)CC1CN(C(=O)COC=2C=CC(Cl)=CC=2)CCN1CC1=CC=C(F)C=C1 RXVCXZLAPQWSTQ-UHFFFAOYSA-N 0.000 claims description 2
- OEKNQPBWBIFMAG-MSOLQXFVSA-N 1-[5-chloro-2-[2-[(2S,5R)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]phenyl]-1-(2,4-dichlorophenyl)urea Chemical compound ClC1=CC(=C(OCC(=O)N2[C@H](CN([C@@H](C2)C)CC2=CC=C(C=C2)F)C)C=C1)N(C(=O)N)C1=C(C=C(C=C1)Cl)Cl OEKNQPBWBIFMAG-MSOLQXFVSA-N 0.000 claims description 2
- WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 claims description 2
- BYZCHSMJYRPVAP-ZCQKWSGTSA-N 1-tert-butyl-3-[2-(4-chlorophenyl)-4-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-4-oxobutyl]urea Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)CC(CNC(=O)NC(C)(C)C)C=2C=CC(Cl)=CC=2)N1CC1=CC=C(F)C=C1 BYZCHSMJYRPVAP-ZCQKWSGTSA-N 0.000 claims description 2
- LXQIAFOVWYILFO-CVEARBPZSA-N 2-(3-chloro-5-methoxyphenoxy)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound COC1=CC(Cl)=CC(OCC(=O)N2[C@H](CN(CC=3C=CC(F)=CC=3)[C@H](C)C2)C)=C1 LXQIAFOVWYILFO-CVEARBPZSA-N 0.000 claims description 2
- BBPPAILTZCQWOZ-CVEARBPZSA-N 2-(4-bromo-3,5-dimethoxyphenoxy)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound COC1=C(Br)C(OC)=CC(OCC(=O)N2[C@H](CN(CC=3C=CC(F)=CC=3)[C@H](C)C2)C)=C1 BBPPAILTZCQWOZ-CVEARBPZSA-N 0.000 claims description 2
- FAHQAIFGDUIFKU-CABCVRRESA-N 2-(4-chloro-2-hydroxyphenoxy)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)O)N1CC1=CC=C(F)C=C1 FAHQAIFGDUIFKU-CABCVRRESA-N 0.000 claims description 2
- SNWXUHYGYBOTCU-CABCVRRESA-N 2-(4-chloro-3-nitrophenoxy)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C=C(C(Cl)=CC=2)[N+]([O-])=O)N1CC1=CC=C(F)C=C1 SNWXUHYGYBOTCU-CABCVRRESA-N 0.000 claims description 2
- QBCVYDLJRSIWDI-HZPDHXFCSA-N 2-(4-chlorophenoxy)-1-[(2r,3r)-4-[(4-fluorophenyl)methyl]-2,3-dimethylpiperazin-1-yl]ethanone Chemical compound C=1C=C(Cl)C=CC=1OCC(=O)N([C@H](C)[C@H]1C)CCN1CC1=CC=C(F)C=C1 QBCVYDLJRSIWDI-HZPDHXFCSA-N 0.000 claims description 2
- NJJKVXLCHMJTQQ-AUSIDOKSSA-N 2-(4-chlorophenoxy)-1-[(2r,5r)-4-[(4-fluorophenyl)methyl]-2-methyl-5-(piperazin-1-ylmethyl)piperazin-1-yl]ethanone Chemical compound C([C@H](N(C[C@H]1CN2CCNCC2)C(=O)COC=2C=CC(Cl)=CC=2)C)N1CC1=CC=C(F)C=C1 NJJKVXLCHMJTQQ-AUSIDOKSSA-N 0.000 claims description 2
- PAZKLODKSQAXRF-VRTSCDAPSA-N 2-(4-chlorophenoxy)-1-[(2r,5r)-4-[(4-fluorophenyl)methyl]-5-(1-hydroxyethyl)-2-methylpiperazin-1-yl]ethanone Chemical compound C([C@@H](C)N(C[C@@H]1C(O)C)C(=O)COC=2C=CC(Cl)=CC=2)N1CC1=CC=C(F)C=C1 PAZKLODKSQAXRF-VRTSCDAPSA-N 0.000 claims description 2
- YPFJUGDHYRXKKS-AYGPBQIHSA-N 2-(4-chlorophenoxy)-1-[(2r,5r)-4-[(4-fluorophenyl)methyl]-5-[hydroxy(phenyl)methyl]-2-methylpiperazin-1-yl]ethanone Chemical compound C([C@H](N(C[C@@H]1C(O)C=2C=CC=CC=2)C(=O)COC=2C=CC(Cl)=CC=2)C)N1CC1=CC=C(F)C=C1 YPFJUGDHYRXKKS-AYGPBQIHSA-N 0.000 claims description 2
- NFZOHNGKYIRFQX-VGSWGCGISA-N 2-(4-chlorophenoxy)-1-[(2r,5s)-5-[(cyclopropylamino)methyl]-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]ethanone Chemical compound C([C@H](N(C[C@@H]1CNC2CC2)C(=O)COC=2C=CC(Cl)=CC=2)C)N1CC1=CC=C(F)C=C1 NFZOHNGKYIRFQX-VGSWGCGISA-N 0.000 claims description 2
- IGKBJHMYMNMMOX-HZPDHXFCSA-N 2-(4-chlorophenoxy)-1-[(2r,6r)-4-[(4-fluorophenyl)methyl]-2,6-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](N([C@H](C)C1)C(=O)COC=2C=CC(Cl)=CC=2)C)N1CC1=CC=C(F)C=C1 IGKBJHMYMNMMOX-HZPDHXFCSA-N 0.000 claims description 2
- HQLNLEFFXBXJIW-HNNXBMFYSA-N 2-(4-chlorophenoxy)-1-[(2s)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]ethanone Chemical compound C([C@@H](N(CC1)C(=O)COC=2C=CC(Cl)=CC=2)C)N1CC1=CC=C(F)C=C1 HQLNLEFFXBXJIW-HNNXBMFYSA-N 0.000 claims description 2
- QBCVYDLJRSIWDI-CVEARBPZSA-N 2-(4-chlorophenoxy)-1-[(2s,3r)-4-[(4-fluorophenyl)methyl]-2,3-dimethylpiperazin-1-yl]ethanone Chemical compound C=1C=C(Cl)C=CC=1OCC(=O)N([C@@H](C)[C@H]1C)CCN1CC1=CC=C(F)C=C1 QBCVYDLJRSIWDI-CVEARBPZSA-N 0.000 claims description 2
- PAUQWKUMTWIOME-HOTGVXAUSA-N 2-(4-chlorophenoxy)-1-[(2s,5s)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@@H]1C)C(=O)COC=2C=CC(Cl)=CC=2)N1CC1=CC=C(F)C=C1 PAUQWKUMTWIOME-HOTGVXAUSA-N 0.000 claims description 2
- UMJRDZUVCDLZOO-HOTGVXAUSA-N 2-(4-chlorophenoxy)-1-[(3s,5s)-4-[(4-fluorophenyl)methyl]-3,5-dimethylpiperazin-1-yl]ethanone Chemical compound N1([C@@H](C)CN(C[C@@H]1C)C(=O)COC=1C=CC(Cl)=CC=1)CC1=CC=C(F)C=C1 UMJRDZUVCDLZOO-HOTGVXAUSA-N 0.000 claims description 2
- GOAFPEYYYMTTTH-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[4-[(4-fluorophenyl)methyl]-2-(hydroxymethyl)piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)COC=2C=CC(Cl)=CC=2)C(CO)CN1CC1=CC=C(F)C=C1 GOAFPEYYYMTTTH-UHFFFAOYSA-N 0.000 claims description 2
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- XNPQXKVAPSQCRS-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[4-[(4-fluorophenyl)methyl]-2-[2-(2-hydroxyethylamino)ethyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)COC=2C=CC(Cl)=CC=2)C(CCNCCO)CN1CC1=CC=C(F)C=C1 XNPQXKVAPSQCRS-UHFFFAOYSA-N 0.000 claims description 2
- JQARHMDDGRDBIS-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[4-[(4-fluorophenyl)methyl]-2-[2-(methylamino)ethyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)COC=2C=CC(Cl)=CC=2)C(CCNC)CN1CC1=CC=C(F)C=C1 JQARHMDDGRDBIS-UHFFFAOYSA-N 0.000 claims description 2
- OKLYCOIISPKTCG-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[4-[(4-fluorophenyl)methyl]-2-[2-[(4-fluorophenyl)methylamino]ethyl]piperazin-1-yl]ethanone Chemical compound C1=CC(F)=CC=C1CNCCC1N(C(=O)COC=2C=CC(Cl)=CC=2)CCN(CC=2C=CC(F)=CC=2)C1 OKLYCOIISPKTCG-UHFFFAOYSA-N 0.000 claims description 2
- VDBCNPPZXMJWTQ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[4-[(4-fluorophenyl)methyl]-3-(2-hydroxy-2-methylpropyl)piperazin-1-yl]ethanone Chemical compound CC(C)(O)CC1CN(C(=O)COC=2C=CC(Cl)=CC=2)CCN1CC1=CC=C(F)C=C1 VDBCNPPZXMJWTQ-UHFFFAOYSA-N 0.000 claims description 2
- HDQMYXHCDVZATI-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[4-[(4-fluorophenyl)methyl]-3-[2-(2-hydroxyethylamino)ethyl]piperazin-1-yl]ethanone Chemical compound OCCNCCC1CN(C(=O)COC=2C=CC(Cl)=CC=2)CCN1CC1=CC=C(F)C=C1 HDQMYXHCDVZATI-UHFFFAOYSA-N 0.000 claims description 2
- IGKRHQPPXDGJRO-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[4-[(4-fluorophenyl)methyl]-3-[2-hydroxy-2-(4-methylphenyl)ethyl]piperazin-1-yl]ethanone Chemical compound C1=CC(C)=CC=C1C(O)CC1N(CC=2C=CC(F)=CC=2)CCN(C(=O)COC=2C=CC(Cl)=CC=2)C1 IGKRHQPPXDGJRO-UHFFFAOYSA-N 0.000 claims description 2
- ZSEOLRYUWAEEMP-CVEARBPZSA-N 2-[4-chloro-2-(hydroxymethyl)phenoxy]-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)CO)N1CC1=CC=C(F)C=C1 ZSEOLRYUWAEEMP-CVEARBPZSA-N 0.000 claims description 2
- VGDCVBHIPBVFGW-UHFFFAOYSA-N 2-[4-chloro-2-(hydroxymethyl)phenoxy]-1-[4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]ethanone Chemical compound C1CN(C(=O)COC=2C(=CC(Cl)=CC=2)CO)C(C)CN1CC1=CC=C(F)C=C1 VGDCVBHIPBVFGW-UHFFFAOYSA-N 0.000 claims description 2
- CYPCBIXIOMGJTM-LJQANCHMSA-N 2-[4-chloro-2-(piperazin-1-ylmethyl)phenoxy]-1-[(2r)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]ethanone Chemical compound C([C@H](N(CC1)C(=O)COC=2C(=CC(Cl)=CC=2)CN2CCNCC2)C)N1CC1=CC=C(F)C=C1 CYPCBIXIOMGJTM-LJQANCHMSA-N 0.000 claims description 2
- PPSHXTNGQPNPSD-VQTJNVASSA-N 2-[4-chloro-2-(piperazin-1-ylmethyl)phenoxy]-1-[(2r,5s)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound C([C@@H](C)N(C[C@@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)CN2CCNCC2)N1CC1=CC=C(F)C=C1 PPSHXTNGQPNPSD-VQTJNVASSA-N 0.000 claims description 2
- XHTFZVPXKOFJNT-DVKDBIPTSA-N 2-[4-chloro-2-[1-(methylamino)ethyl]phenoxy]-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]ethanone Chemical compound CNC(C)C1=CC(Cl)=CC=C1OCC(=O)N1[C@@H](C)CN(CC=2C=CC(F)=CC=2)[C@H](C)C1 XHTFZVPXKOFJNT-DVKDBIPTSA-N 0.000 claims description 2
- ITSIKNOBUDJYAF-JKSUJKDBSA-N 2-amino-n-[5-chloro-2-[2-[(2r,5s)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]phenyl]acetamide Chemical compound C([C@@H](C)N(C[C@@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)NC(=O)CN)N1CC1=CC=C(F)C=C1 ITSIKNOBUDJYAF-JKSUJKDBSA-N 0.000 claims description 2
- ITSIKNOBUDJYAF-CVEARBPZSA-N 2-amino-n-[5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]phenyl]acetamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)NC(=O)CN)N1CC1=CC=C(F)C=C1 ITSIKNOBUDJYAF-CVEARBPZSA-N 0.000 claims description 2
- OLWFWMWIVIAJJE-ZQIYAJFXSA-N 3-amino-3-(4-chlorophenyl)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]propan-1-one Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)CC(N)C=2C=CC(Cl)=CC=2)N1CC1=CC=C(F)C=C1 OLWFWMWIVIAJJE-ZQIYAJFXSA-N 0.000 claims description 2
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- QYCCZNUUPIATOP-RPWUZVMVSA-N 4-[[5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]phenyl]methyl]-n-(2-fluorophenyl)piperazine-1-carboxamide Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)COC=2C(=CC(Cl)=CC=2)CN2CCN(CC2)C(=O)NC=2C(=CC=CC=2)F)N1CC1=CC=C(F)C=C1 QYCCZNUUPIATOP-RPWUZVMVSA-N 0.000 claims description 2
- LBKXYZQGASUAAK-LIHHCBPRSA-N 4-amino-3-(4-chlorophenyl)-1-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]butan-1-one Chemical compound C([C@H](C)N(C[C@H]1C)C(=O)CC(CN)C=2C=CC(Cl)=CC=2)N1CC1=CC=C(F)C=C1 LBKXYZQGASUAAK-LIHHCBPRSA-N 0.000 claims description 2
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- BJHPQYADERQBIO-CVEARBPZSA-N 5-chloro-2-[2-[(2s,5r)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]-n-methylbenzamide Chemical compound CNC(=O)C1=CC(Cl)=CC=C1OCC(=O)N1[C@@H](C)CN(CC=2C=CC(F)=CC=2)[C@H](C)C1 BJHPQYADERQBIO-CVEARBPZSA-N 0.000 claims description 2
- YXHJEEYJZHVTMD-BEFAXECRSA-N [(2s,5r)-4-[2-(4-chlorophenoxy)acetyl]-1-[(4-fluorophenyl)methyl]-5-methylpiperazin-2-yl]methyl carbamate Chemical compound C([C@H](N(C[C@H]1COC(N)=O)C(=O)COC=2C=CC(Cl)=CC=2)C)N1CC1=CC=C(F)C=C1 YXHJEEYJZHVTMD-BEFAXECRSA-N 0.000 claims description 2
- PCHWJEBNTIAEKW-UHFFFAOYSA-N [4-[2-(4-chlorophenoxy)acetyl]-1-[(4-fluorophenyl)methyl]-6-methylpiperazin-2-yl]methyl 2-(4-chlorophenoxy)acetate Chemical compound C=1C=C(F)C=CC=1CN1C(C)CN(C(=O)COC=2C=CC(Cl)=CC=2)CC1COC(=O)COC1=CC=C(Cl)C=C1 PCHWJEBNTIAEKW-UHFFFAOYSA-N 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- WDCLHPZCPXMTBN-UHFFFAOYSA-N ethyl 4-[2-(4-chlorophenoxy)acetyl]-1-[(4-fluorophenyl)methyl]piperazine-2-carboxylate Chemical compound CCOC(=O)C1CN(C(=O)COC=2C=CC(Cl)=CC=2)CCN1CC1=CC=C(F)C=C1 WDCLHPZCPXMTBN-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/18—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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US87359997A | 1997-06-12 | 1997-06-12 | |
US09/094,397 US6207665B1 (en) | 1997-06-12 | 1998-06-09 | Piperazine derivatives and their use as anti-inflammatory agents |
PCT/EP1998/003503 WO1998056771A2 (en) | 1997-06-12 | 1998-06-11 | Piperazine derivatives and their use as anti-inflammatory agents |
Publications (3)
Publication Number | Publication Date |
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NO996068D0 NO996068D0 (no) | 1999-12-09 |
NO996068L NO996068L (no) | 2000-02-11 |
NO317343B1 true NO317343B1 (no) | 2004-10-11 |
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NO19996068A NO317343B1 (no) | 1997-06-12 | 1999-12-09 | Piperazinderivater og deres anvendelse som anti-inflammatoriske midler |
NO20031373A NO20031373D0 (no) | 1997-06-12 | 2003-03-26 | Piperazinderivater og deres anvendelse som antiinflammatoriske midler |
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NO20031373A NO20031373D0 (no) | 1997-06-12 | 2003-03-26 | Piperazinderivater og deres anvendelse som antiinflammatoriske midler |
Country Status (22)
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- 1998-06-11 DE DE69811363T patent/DE69811363T2/de not_active Expired - Fee Related
- 1998-06-11 KR KR1019997011718A patent/KR100549137B1/ko not_active IP Right Cessation
- 1998-06-11 CA CA002293382A patent/CA2293382C/en not_active Expired - Fee Related
- 1998-06-11 JP JP50161199A patent/JP2002503239A/ja not_active Ceased
- 1998-06-11 AT AT98937467T patent/ATE232522T1/de not_active IP Right Cessation
- 1998-06-11 EE EEP200200682A patent/EE200200682A/xx unknown
- 1998-06-11 EE EEP200200683A patent/EE200200683A/xx unknown
- 1998-06-11 WO PCT/EP1998/003503 patent/WO1998056771A2/en active IP Right Grant
- 1998-06-11 SK SK1713-99A patent/SK285162B6/sk unknown
- 1998-06-11 HU HU0003929A patent/HUP0003929A3/hu unknown
- 1998-06-11 DK DK02090193T patent/DK1254899T3/da active
- 1998-06-11 EP EP98937467A patent/EP0988292B1/en not_active Expired - Lifetime
- 1998-06-11 ES ES02090193T patent/ES2242824T3/es not_active Expired - Lifetime
- 1998-06-11 SK SK79-2005A patent/SK285445B6/sk unknown
- 1998-06-11 DE DE69830341T patent/DE69830341T2/de not_active Expired - Fee Related
- 1998-06-11 EE EEP200200684A patent/EE200200684A/xx unknown
- 1998-06-11 AU AU86258/98A patent/AU735462B2/en not_active Ceased
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1999
- 1999-11-19 IS IS5258A patent/IS2241B/is unknown
- 1999-12-09 NO NO19996068A patent/NO317343B1/no unknown
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2000
- 2000-11-14 US US09/713,606 patent/US6541476B1/en not_active Expired - Fee Related
- 2000-11-15 US US09/713,881 patent/US6534509B1/en not_active Expired - Fee Related
- 2000-11-16 US US09/714,937 patent/US6573266B1/en not_active Expired - Fee Related
- 2000-11-29 US US09/726,808 patent/US6555537B2/en not_active Expired - Fee Related
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2003
- 2003-01-17 US US10/347,529 patent/US6972290B2/en not_active Expired - Fee Related
- 2003-01-17 US US10/347,530 patent/US6977258B2/en not_active Expired - Fee Related
- 2003-03-26 NO NO20031373A patent/NO20031373D0/no not_active Application Discontinuation
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2005
- 2005-10-13 US US11/248,618 patent/US7268140B2/en not_active Expired - Fee Related
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