AU660180B2 - 1-acylpiperidine compounds - Google Patents

Info

Publication number

AU660180B2

AU660180B2 AU20965/92A AU2096592A AU660180B2 AU 660180 B2 AU660180 B2 AU 660180B2 AU 20965/92 A AU20965/92 A AU 20965/92A AU 2096592 A AU2096592 A AU 2096592A AU 660180 B2 AU660180 B2 AU 660180B2

Authority

AU

Australia

Prior art keywords

piperidinamine

benzyl

salt

dimethylbenzoyl

radical

Prior art date

1991-08-12

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Ceased

Links

• Espacenet
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 302
• -1 heteroaroyl Chemical group 0.000 claims abstract description 237
• 150000003839 salts Chemical class 0.000 claims abstract description 171
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 59
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 57
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 56
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 51
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 45
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 44
• 239000001257 hydrogen Substances 0.000 claims abstract description 44
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 39
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 24
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 18
• 239000013543 active substance Substances 0.000 claims abstract description 16
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 16
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims abstract description 13
• 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 13
• 125000003435 aroyl group Chemical group 0.000 claims abstract description 12
• 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 9
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 9
• 208000035475 disorder Diseases 0.000 claims abstract description 9
• IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims abstract description 7
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims abstract description 7
• 125000004475 heteroaralkyl group Chemical group 0.000 claims abstract description 6
• QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 claims abstract description 5
• 102100024304 Protachykinin-1 Human genes 0.000 claims abstract description 5
• 101800003906 Substance P Proteins 0.000 claims abstract description 5
• 125000001589 carboacyl group Chemical group 0.000 claims abstract 18
• 239000003814 drug Substances 0.000 claims abstract 2
• 239000000203 mixture Substances 0.000 claims description 78
• 229910052736 halogen Inorganic materials 0.000 claims description 70
• 150000002367 halogens Chemical class 0.000 claims description 68
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 49
• 150000003254 radicals Chemical class 0.000 claims description 43
• 238000000034 method Methods 0.000 claims description 39
• 125000003545 alkoxy group Chemical group 0.000 claims description 38
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 34
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 34
• 230000002829 reductive effect Effects 0.000 claims description 34
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
• 150000002431 hydrogen Chemical class 0.000 claims description 25
• 125000004043 oxo group Chemical group O=* 0.000 claims description 20
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 19
• BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 claims description 19
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
• 238000002360 preparation method Methods 0.000 claims description 17
• 125000001624 naphthyl group Chemical group 0.000 claims description 16
• LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 claims description 16
• 239000003795 chemical substances by application Substances 0.000 claims description 15
• VRJHQPZVIGNGMX-UHFFFAOYSA-N piperidine-4-one Natural products O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 claims description 15
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
• 125000002950 monocyclic group Chemical group 0.000 claims description 12
• 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 9
• 125000004076 pyridyl group Chemical group 0.000 claims description 9
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 8
• 229940127557 pharmaceutical product Drugs 0.000 claims description 8
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
• 125000002619 bicyclic group Chemical group 0.000 claims description 7
• 125000005493 quinolyl group Chemical group 0.000 claims description 7
• 125000001041 indolyl group Chemical group 0.000 claims description 6
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
• 125000005843 halogen group Chemical group 0.000 claims description 5
• 125000001425 triazolyl group Chemical group 0.000 claims description 5
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 4
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 4
• 108090000765 processed proteins & peptides Proteins 0.000 claims description 4
• 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims description 4
• 239000000654 additive Substances 0.000 claims description 3
• 150000005840 aryl radicals Chemical class 0.000 claims description 3
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 241001465754 Metazoa Species 0.000 claims description 2
• TUJAYMPVNFTEHA-LOSJGSFVSA-N [(2r,4s)-2-benzyl-4-(1h-indol-3-ylmethylamino)piperidin-1-yl]-(3,5-dichlorophenyl)methanone Chemical compound ClC1=CC(Cl)=CC(C(=O)N2[C@@H](C[C@H](CC2)NCC=2C3=CC=CC=C3NC=2)CC=2C=CC=CC=2)=C1 TUJAYMPVNFTEHA-LOSJGSFVSA-N 0.000 claims description 2
• HLGUXCWJAHTKJK-RRPNLBNLSA-N [(2r,4s)-2-benzyl-4-(quinolin-3-ylmethylamino)piperidin-1-yl]-[3,5-bis(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C(=O)N2[C@@H](C[C@H](CC2)NCC=2C=C3C=CC=CC3=NC=2)CC=2C=CC=CC=2)=C1 HLGUXCWJAHTKJK-RRPNLBNLSA-N 0.000 claims description 2
• PFTLOBQREFSYPO-IZZNHLLZSA-N [(2r,4s)-2-benzyl-4-(quinolin-4-ylmethylamino)piperidin-1-yl]-(3,5-dimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(C(=O)N2[C@@H](C[C@H](CC2)NCC=2C3=CC=CC=C3N=CC=2)CC=2C=CC=CC=2)=C1 PFTLOBQREFSYPO-IZZNHLLZSA-N 0.000 claims description 2
• WYWZULLPWPXJOX-RRPNLBNLSA-N [(2r,4s)-2-benzyl-4-[(2,3-dimethoxyphenyl)methylamino]piperidin-1-yl]-(3,5-dimethylphenyl)methanone Chemical compound COC1=CC=CC(CN[C@@H]2C[C@@H](CC=3C=CC=CC=3)N(CC2)C(=O)C=2C=C(C)C=C(C)C=2)=C1OC WYWZULLPWPXJOX-RRPNLBNLSA-N 0.000 claims description 2
• PCNBIVOAEVUXQV-IZZNHLLZSA-N [(2r,4s)-2-benzyl-4-[(2,6-dimethoxyphenyl)methylamino]piperidin-1-yl]-(3,5-dimethylphenyl)methanone Chemical compound COC1=CC=CC(OC)=C1CN[C@@H]1C[C@@H](CC=2C=CC=CC=2)N(C(=O)C=2C=C(C)C=C(C)C=2)CC1 PCNBIVOAEVUXQV-IZZNHLLZSA-N 0.000 claims description 2
• WUGVOQASTNTNGI-RRPNLBNLSA-N [(2r,4s)-2-benzyl-4-[(2-methoxyphenyl)methylamino]piperidin-1-yl]-(3,5-dimethylphenyl)methanone Chemical compound COC1=CC=CC=C1CN[C@@H]1C[C@@H](CC=2C=CC=CC=2)N(C(=O)C=2C=C(C)C=C(C)C=2)CC1 WUGVOQASTNTNGI-RRPNLBNLSA-N 0.000 claims description 2
• PQSYSEWPJRXXCO-LOSJGSFVSA-N [(2r,4s)-2-benzyl-4-[(4-chlorophenyl)methylamino]piperidin-1-yl]-(3,5-dichlorophenyl)methanone Chemical compound C1=CC(Cl)=CC=C1CN[C@@H]1C[C@@H](CC=2C=CC=CC=2)N(C(=O)C=2C=C(Cl)C=C(Cl)C=2)CC1 PQSYSEWPJRXXCO-LOSJGSFVSA-N 0.000 claims description 2
• DIYXLNGZTJKRBH-SVBPBHIXSA-N [(2s,4s)-2-benzyl-4-(quinolin-3-ylmethylamino)piperidin-1-yl]-(3,5-dimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(C(=O)N2[C@H](C[C@H](CC2)NCC=2C=C3C=CC=CC3=NC=2)CC=2C=CC=CC=2)=C1 DIYXLNGZTJKRBH-SVBPBHIXSA-N 0.000 claims description 2
• KDWUAXPZIZPYHY-NSOVKSMOSA-N [(2s,4s)-2-benzyl-4-[2-(2-methoxyphenyl)ethylamino]piperidin-1-yl]-(3,5-dimethylphenyl)methanone Chemical compound COC1=CC=CC=C1CCN[C@@H]1C[C@H](CC=2C=CC=CC=2)N(C(=O)C=2C=C(C)C=C(C)C=2)CC1 KDWUAXPZIZPYHY-NSOVKSMOSA-N 0.000 claims description 2
• PDYPBTDIGRMZNK-SVBPBHIXSA-N [(2s,4s)-2-benzyl-4-[3-(3-chlorophenyl)propylamino]piperidin-1-yl]-(3,5-dimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(C(=O)N2[C@H](C[C@H](CC2)NCCCC=2C=C(Cl)C=CC=2)CC=2C=CC=CC=2)=C1 PDYPBTDIGRMZNK-SVBPBHIXSA-N 0.000 claims description 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
• 229910052705 radium Inorganic materials 0.000 claims description 2
• 229910052701 rubidium Inorganic materials 0.000 claims description 2
• 239000008194 pharmaceutical composition Substances 0.000 claims 2
• PJDOVGDUMXUTHB-IZZNHLLZSA-N (2R,4S)-2-benzyl-1-[(2,4-dichlorophenyl)methyl]-N-(quinolin-4-ylmethyl)piperidin-4-amine Chemical compound ClC1=CC(Cl)=CC=C1CN1[C@H](CC=2C=CC=CC=2)C[C@@H](NCC=2C3=CC=CC=C3N=CC=2)CC1 PJDOVGDUMXUTHB-IZZNHLLZSA-N 0.000 claims 1
• GZORDCHPGPLJNH-WUFINQPMSA-N (2R,4S)-2-benzyl-N,1-bis(quinolin-4-ylmethyl)piperidin-4-amine Chemical compound C([C@H]1N(CC=2C3=CC=CC=C3N=CC=2)CC[C@@H](C1)NCC=1C2=CC=CC=C2N=CC=1)C1=CC=CC=C1 GZORDCHPGPLJNH-WUFINQPMSA-N 0.000 claims 1
• KCHZSHRRZWMRFQ-RRPNLBNLSA-N (2r,4s)-2-benzyl-1-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-(quinolin-4-ylmethyl)piperidin-4-amine Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(CN2[C@@H](C[C@H](CC2)NCC=2C3=CC=CC=C3N=CC=2)CC=2C=CC=CC=2)=C1 KCHZSHRRZWMRFQ-RRPNLBNLSA-N 0.000 claims 1
• VJUXBLWRJQYXEJ-UHFFFAOYSA-N (3,5-dimethylphenyl)-[2-phenyl-4-(quinolin-4-ylmethylamino)piperidin-1-yl]methanone Chemical compound CC1=CC(C)=CC(C(=O)N2C(CC(CC2)NCC=2C3=CC=CC=C3N=CC=2)C=2C=CC=CC=2)=C1 VJUXBLWRJQYXEJ-UHFFFAOYSA-N 0.000 claims 1
• UNGLLXYYFQWJQO-RRPNLBNLSA-N 1-[(2R,4S)-2-benzyl-4-(quinolin-4-ylmethylamino)piperidin-1-yl]-2-(4-chlorophenyl)ethanone Chemical compound C1=CC(Cl)=CC=C1CC(=O)N1[C@H](CC=2C=CC=CC=2)C[C@@H](NCC=2C3=CC=CC=C3N=CC=2)CC1 UNGLLXYYFQWJQO-RRPNLBNLSA-N 0.000 claims 1
• QEDDFVHLAFIWMP-IZZNHLLZSA-N 1-[(2R,4S)-2-benzyl-4-(quinolin-4-ylmethylamino)piperidin-1-yl]-2-pyridin-2-ylethanone Chemical compound N1([C@@H](C[C@H](CC1)NCC=1C2=CC=CC=C2N=CC=1)CC=1C=CC=CC=1)C(=O)CC1=CC=CC=N1 QEDDFVHLAFIWMP-IZZNHLLZSA-N 0.000 claims 1
• HVFGGKAAGSRBLP-IZZNHLLZSA-N 1-[(2R,4S)-2-benzyl-4-(quinolin-4-ylmethylamino)piperidin-1-yl]-2-pyridin-4-ylethanone Chemical compound N1([C@@H](C[C@H](CC1)NCC=1C2=CC=CC=C2N=CC=1)CC=1C=CC=CC=1)C(=O)CC1=CC=NC=C1 HVFGGKAAGSRBLP-IZZNHLLZSA-N 0.000 claims 1
• FUJSJWRORKKPAI-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)acetyl chloride Chemical compound ClC(=O)COC1=CC=C(Cl)C=C1Cl FUJSJWRORKKPAI-UHFFFAOYSA-N 0.000 claims 1
• 125000000301 2-(3-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
• VQUMPBVNOGTKDC-XZOQPEGZSA-N N-[(2R,4S)-2-benzyl-1-(3,5-dichlorobenzoyl)piperidin-4-yl]-1H-indole-3-carboxamide Chemical compound ClC1=CC(Cl)=CC(C(=O)N2[C@@H](C[C@H](CC2)NC(=O)C=2C3=CC=CC=C3NC=2)CC=2C=CC=CC=2)=C1 VQUMPBVNOGTKDC-XZOQPEGZSA-N 0.000 claims 1
• 150000007945 N-acyl ureas Chemical class 0.000 claims 1
• HSSZIZURYDLFBR-IZZNHLLZSA-N [(2R,4S)-2-benzyl-4-(2-phenylethylamino)piperidin-1-yl]-(3,5-dichlorophenyl)methanone Chemical compound ClC1=CC(Cl)=CC(C(=O)N2[C@@H](C[C@H](CC2)NCCC=2C=CC=CC=2)CC=2C=CC=CC=2)=C1 HSSZIZURYDLFBR-IZZNHLLZSA-N 0.000 claims 1
• GMRGTANIXBAITC-BJKOFHAPSA-N [(2R,4S)-2-benzyl-4-(quinolin-4-ylmethylamino)piperidin-1-yl]-(2,4-dichlorophenyl)methanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)N1[C@H](CC=2C=CC=CC=2)C[C@@H](NCC=2C3=CC=CC=C3N=CC=2)CC1 GMRGTANIXBAITC-BJKOFHAPSA-N 0.000 claims 1
• LEUPFBCFTGVXOL-RRPNLBNLSA-N [(2R,4S)-2-benzyl-4-(quinolin-4-ylmethylamino)piperidin-1-yl]-(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)N2[C@@H](C[C@H](CC2)NCC=2C3=CC=CC=C3N=CC=2)CC=2C=CC=CC=2)=C1 LEUPFBCFTGVXOL-RRPNLBNLSA-N 0.000 claims 1
• CXAMYWCVLTUBSH-RRPNLBNLSA-N [(2R,4S)-2-benzyl-4-(quinolin-4-ylmethylamino)piperidin-1-yl]-quinolin-2-ylmethanone Chemical compound C([C@@H]1C[C@H](CCN1C(=O)C=1N=C2C=CC=CC2=CC=1)NCC=1C2=CC=CC=C2N=CC=1)C1=CC=CC=C1 CXAMYWCVLTUBSH-RRPNLBNLSA-N 0.000 claims 1
• YKVYHVHNCZRXFP-LOSJGSFVSA-N [(2R,4S)-2-benzyl-4-[(2-methoxyphenyl)methylamino]piperidin-1-yl]-(3,5-dichlorophenyl)methanone Chemical compound COC1=CC=CC=C1CN[C@@H]1C[C@@H](CC=2C=CC=CC=2)N(C(=O)C=2C=C(Cl)C=C(Cl)C=2)CC1 YKVYHVHNCZRXFP-LOSJGSFVSA-N 0.000 claims 1
• MGZFVRUXZAEKNI-XZWHSSHBSA-N [(2R,4S)-4-(benzhydrylamino)-2-benzylpiperidin-1-yl]-(3,5-dichlorophenyl)methanone Chemical compound ClC1=CC(Cl)=CC(C(=O)N2[C@@H](C[C@H](CC2)NC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC=2C=CC=CC=2)=C1 MGZFVRUXZAEKNI-XZWHSSHBSA-N 0.000 claims 1
• PKPKUYSFERUYMH-KAYWLYCHSA-N [(2r,4r)-2-benzyl-4-(benzylamino)piperidin-1-yl]-(3,5-dimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C(=O)N2[C@@H](C[C@@H](CC2)NCC=2C=CC=CC=2)CC=2C=CC=CC=2)=C1 PKPKUYSFERUYMH-KAYWLYCHSA-N 0.000 claims 1
• JDQGLMDJXLPFTR-CLJLJLNGSA-N [(2r,4r)-2-benzyl-4-(pyridin-3-ylmethylamino)piperidin-1-yl]-(3,5-dimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C(=O)N2[C@@H](C[C@@H](CC2)NCC=2C=NC=CC=2)CC=2C=CC=CC=2)=C1 JDQGLMDJXLPFTR-CLJLJLNGSA-N 0.000 claims 1
• ZUVRLHQMDUAXKL-CLJLJLNGSA-N [(2r,4r)-2-benzyl-4-(pyridin-4-ylmethylamino)piperidin-1-yl]-(3,5-dimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C(=O)N2[C@@H](C[C@@H](CC2)NCC=2C=CN=CC=2)CC=2C=CC=CC=2)=C1 ZUVRLHQMDUAXKL-CLJLJLNGSA-N 0.000 claims 1
• PQZHGICZAUJLST-AZGAKELHSA-N [(2r,4s)-2-benzyl-4-(1h-indol-2-ylmethylamino)piperidin-1-yl]-[3,5-bis(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C(=O)N2[C@@H](C[C@H](CC2)NCC=2NC3=CC=CC=C3C=2)CC=2C=CC=CC=2)=C1 PQZHGICZAUJLST-AZGAKELHSA-N 0.000 claims 1
• APRYEVDETHQGAN-LOSJGSFVSA-N [(2r,4s)-2-benzyl-4-(2,3-dihydro-1,4-benzodioxin-6-ylmethylamino)piperidin-1-yl]-(3,5-dichlorophenyl)methanone Chemical compound ClC1=CC(Cl)=CC(C(=O)N2[C@@H](C[C@H](CC2)NCC=2C=C3OCCOC3=CC=2)CC=2C=CC=CC=2)=C1 APRYEVDETHQGAN-LOSJGSFVSA-N 0.000 claims 1
• VOVHTUDFAWJPKO-LOSJGSFVSA-N [(2r,4s)-2-benzyl-4-(2,3-dihydro-1,4-benzodioxin-6-ylmethylamino)piperidin-1-yl]-(3,5-dimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(C(=O)N2[C@@H](C[C@H](CC2)NCC=2C=C3OCCOC3=CC=2)CC=2C=CC=CC=2)=C1 VOVHTUDFAWJPKO-LOSJGSFVSA-N 0.000 claims 1
• KQIGNERNDOIJSB-AHKZPQOWSA-N [(2r,4s)-2-benzyl-4-(quinolin-2-ylmethylamino)piperidin-1-yl]-[3,5-bis(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C(=O)N2[C@@H](C[C@H](CC2)NCC=2N=C3C=CC=CC3=CC=2)CC=2C=CC=CC=2)=C1 KQIGNERNDOIJSB-AHKZPQOWSA-N 0.000 claims 1
• DOXKBIISJMVOAL-BJKOFHAPSA-N [(2r,4s)-2-benzyl-4-(quinolin-4-ylmethylamino)piperidin-1-yl]-(3,5-dihydroxyphenyl)methanone Chemical compound OC1=CC(O)=CC(C(=O)N2[C@@H](C[C@H](CC2)NCC=2C3=CC=CC=C3N=CC=2)CC=2C=CC=CC=2)=C1 DOXKBIISJMVOAL-BJKOFHAPSA-N 0.000 claims 1
• MWWOEKASVSVWFT-IZZNHLLZSA-N [(2r,4s)-2-benzyl-4-(quinolin-4-ylmethylamino)piperidin-1-yl]-(3-chlorophenyl)methanone Chemical compound ClC1=CC=CC(C(=O)N2[C@@H](C[C@H](CC2)NCC=2C3=CC=CC=C3N=CC=2)CC=2C=CC=CC=2)=C1 MWWOEKASVSVWFT-IZZNHLLZSA-N 0.000 claims 1
• OLVLKOUBLOOVQV-BJKOFHAPSA-N [(2r,4s)-2-benzyl-4-[(2-chlorophenyl)methylamino]piperidin-1-yl]-(3,5-dimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(C(=O)N2[C@@H](C[C@H](CC2)NCC=2C(=CC=CC=2)Cl)CC=2C=CC=CC=2)=C1 OLVLKOUBLOOVQV-BJKOFHAPSA-N 0.000 claims 1
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• UWRUVZJQHIMCHS-LOSJGSFVSA-N [(2r,4s)-2-benzyl-4-[(3-chlorophenyl)methylamino]piperidin-1-yl]-[3,5-bis(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C(=O)N2[C@@H](C[C@H](CC2)NCC=2C=C(Cl)C=CC=2)CC=2C=CC=CC=2)=C1 UWRUVZJQHIMCHS-LOSJGSFVSA-N 0.000 claims 1
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• YOXWOVFZJFASQC-LOSJGSFVSA-N [(2r,4s)-2-benzyl-4-[(4-chlorophenyl)methylamino]piperidin-1-yl]-[3,5-bis(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C(=O)N2[C@@H](C[C@H](CC2)NCC=2C=CC(Cl)=CC=2)CC=2C=CC=CC=2)=C1 YOXWOVFZJFASQC-LOSJGSFVSA-N 0.000 claims 1
• OKUMOBQHPIRAKC-LOSJGSFVSA-N [(2r,4s)-2-benzyl-4-[2-(2-chlorophenyl)ethylamino]piperidin-1-yl]-(3,5-dichlorophenyl)methanone Chemical compound ClC1=CC(Cl)=CC(C(=O)N2[C@@H](C[C@H](CC2)NCCC=2C(=CC=CC=2)Cl)CC=2C=CC=CC=2)=C1 OKUMOBQHPIRAKC-LOSJGSFVSA-N 0.000 claims 1
• WFXCKZUOELVXBT-IZZNHLLZSA-N [(2r,4s)-2-benzyl-4-[2-(3-chlorophenyl)ethylamino]piperidin-1-yl]-[3,5-bis(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C(=O)N2[C@@H](C[C@H](CC2)NCCC=2C=C(Cl)C=CC=2)CC=2C=CC=CC=2)=C1 WFXCKZUOELVXBT-IZZNHLLZSA-N 0.000 claims 1
• GECWGHFATMZTQV-IZZNHLLZSA-N [(2r,4s)-2-benzyl-4-[2-(4-chlorophenyl)ethylamino]piperidin-1-yl]-(3,5-dichlorophenyl)methanone Chemical compound C1=CC(Cl)=CC=C1CCN[C@@H]1C[C@@H](CC=2C=CC=CC=2)N(C(=O)C=2C=C(Cl)C=C(Cl)C=2)CC1 GECWGHFATMZTQV-IZZNHLLZSA-N 0.000 claims 1
• SDGGPHPCGPDYIM-WUFINQPMSA-N [(2r,4s)-2-benzyl-4-[2-(4-chlorophenyl)ethylamino]piperidin-1-yl]-(3,5-dimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C(=O)N2[C@@H](C[C@H](CC2)NCCC=2C=CC(Cl)=CC=2)CC=2C=CC=CC=2)=C1 SDGGPHPCGPDYIM-WUFINQPMSA-N 0.000 claims 1
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• LTTUVDZBVBWCOM-SVBPBHIXSA-N [(2s,4s)-2-benzyl-4-[3-(3-chlorophenyl)propylamino]piperidin-1-yl]-[3,5-bis(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C(=O)N2[C@H](C[C@H](CC2)NCCCC=2C=C(Cl)C=CC=2)CC=2C=CC=CC=2)=C1 LTTUVDZBVBWCOM-SVBPBHIXSA-N 0.000 claims 1
• UPOSNCBVBMUMEF-NSOVKSMOSA-N [(2s,4s)-2-benzyl-4-[3-[2-(trifluoromethyl)phenyl]propylamino]piperidin-1-yl]-(3,5-dimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C(=O)N2[C@H](C[C@H](CC2)NCCCC=2C(=CC=CC=2)C(F)(F)F)CC=2C=CC=CC=2)=C1 UPOSNCBVBMUMEF-NSOVKSMOSA-N 0.000 claims 1
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