JP3857270B2 - ケモカイン受容体活性のモジュレーターとして有用なピペリジン誘導体 - Google Patents

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Publication number

JP3857270B2

JP3857270B2 JP2003510654A JP2003510654A JP3857270B2 JP 3857270 B2 JP3857270 B2 JP 3857270B2 JP 2003510654 A JP2003510654 A JP 2003510654A JP 2003510654 A JP2003510654 A JP 2003510654A JP 3857270 B2 JP3857270 B2 JP 3857270B2

Authority

JP

Japan

Prior art keywords

carbonyl

alkyl

bipiperidin

dichlorophenoxy

benzenesulfonamide

Prior art date

2001-07-02

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.)

Expired - Fee Related

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• 230000000694 effects Effects 0.000 title description 13
• 102000009410 Chemokine receptor Human genes 0.000 title description 5
• 108050000299 Chemokine receptor Proteins 0.000 title description 5
• 150000003053 piperidines Chemical class 0.000 title description 3
• 125000000217 alkyl group Chemical group 0.000 claims description 278
• 150000001875 compounds Chemical class 0.000 claims description 208
• -1 nitro, hydroxy Chemical group 0.000 claims description 72
• 238000000034 method Methods 0.000 claims description 63
• 229910052739 hydrogen Inorganic materials 0.000 claims description 60
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 46
• 239000001257 hydrogen Substances 0.000 claims description 45
• 239000002904 solvent Substances 0.000 claims description 43
• 125000003545 alkoxy group Chemical group 0.000 claims description 35
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
• 150000003839 salts Chemical class 0.000 claims description 33
• 229910052736 halogen Inorganic materials 0.000 claims description 30
• 150000002367 halogens Chemical class 0.000 claims description 30
• 125000000623 heterocyclic group Chemical group 0.000 claims description 25
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
• 238000004519 manufacturing process Methods 0.000 claims description 14
• 239000012453 solvate Substances 0.000 claims description 12
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 11
• 239000000460 chlorine Substances 0.000 claims description 11
• 150000002431 hydrogen Chemical class 0.000 claims description 11
• 229910052757 nitrogen Inorganic materials 0.000 claims description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 9
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
• 125000001072 heteroaryl group Chemical group 0.000 claims description 9
• 125000004043 oxo group Chemical group O=* 0.000 claims description 9
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
• 125000003118 aryl group Chemical group 0.000 claims description 7
• 229910052801 chlorine Inorganic materials 0.000 claims description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• QVLZVRFIGXNZMN-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 QVLZVRFIGXNZMN-UHFFFAOYSA-N 0.000 claims description 6
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
• 125000003107 substituted aryl group Chemical group 0.000 claims description 6
• 150000001204 N-oxides Chemical class 0.000 claims description 5
• KINKZEDQCGUBRF-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 KINKZEDQCGUBRF-UHFFFAOYSA-N 0.000 claims description 5
• YRYUWEQXLZBDLN-UHFFFAOYSA-N 3-cyano-n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonylbenzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C=2C=C(C=CC=2)C#N)CC1 YRYUWEQXLZBDLN-UHFFFAOYSA-N 0.000 claims description 4
• ZDWNUSDUXVXKFB-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-propan-2-ylsulfonylpiperidine-1-carboxamide Chemical compound C1CN(C(=O)NS(=O)(=O)C(C)C)CCC1N1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 ZDWNUSDUXVXKFB-UHFFFAOYSA-N 0.000 claims description 4
• NVKOAYGOEXSEII-WGSAOQKQSA-N C1=CC(C)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 NVKOAYGOEXSEII-WGSAOQKQSA-N 0.000 claims description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
• 150000001266 acyl halides Chemical class 0.000 claims description 4
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 229940124530 sulfonamide Drugs 0.000 claims description 4
• WKHAUPVZXUOYTL-UHFFFAOYSA-N 2-chloro-n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonylbenzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C=2C(=CC=CC=2)Cl)CC1 WKHAUPVZXUOYTL-UHFFFAOYSA-N 0.000 claims description 3
• REIZYHKXRGEBEI-UHFFFAOYSA-N 4-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]-n-(2-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=C(C)C(Cl)=CC=2)Cl)CC1 REIZYHKXRGEBEI-UHFFFAOYSA-N 0.000 claims description 3
• HZUZFBPRVMJMHT-UHFFFAOYSA-N 4-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]-n-(4-fluorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=C(Cl)C=CC(OC2CCN(CC2)C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=CC(F)=CC=2)=C1Cl HZUZFBPRVMJMHT-UHFFFAOYSA-N 0.000 claims description 3
• FHLJNJSZPGMALO-UHFFFAOYSA-N 4-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=C(Cl)C(Cl)=CC=2)C)CC1 FHLJNJSZPGMALO-UHFFFAOYSA-N 0.000 claims description 3
• IUWXMHJXYHLXSR-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(2,4,5-trifluorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=C(F)C(F)=CC(F)=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 IUWXMHJXYHLXSR-UHFFFAOYSA-N 0.000 claims description 3
• YISQPKPMJJVCCU-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(2,5-dichlorothiophen-3-yl)sulfonylpiperidine-1-carboxamide Chemical compound S1C(Cl)=CC(S(=O)(=O)NC(=O)N2CCC(CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1Cl YISQPKPMJJVCCU-UHFFFAOYSA-N 0.000 claims description 3
• SWEHCFKMAYPEHK-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(2,5-difluorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound FC1=CC=C(F)C(S(=O)(=O)NC(=O)N2CCC(CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 SWEHCFKMAYPEHK-UHFFFAOYSA-N 0.000 claims description 3
• IGLADUDHPDHSRD-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(2-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 IGLADUDHPDHSRD-UHFFFAOYSA-N 0.000 claims description 3
• CPGNWUXPMNXYJX-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(3,5-dichlorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound ClC1=CC(Cl)=CC(S(=O)(=O)NC(=O)N2CCC(CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 CPGNWUXPMNXYJX-UHFFFAOYSA-N 0.000 claims description 3
• FRYRCDHNALIZSR-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-[2-(trifluoromethoxy)phenyl]sulfonylpiperidine-1-carboxamide Chemical compound FC(F)(F)OC1=CC=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 FRYRCDHNALIZSR-UHFFFAOYSA-N 0.000 claims description 3
• HHYBIQJOLMHLOC-UHFFFAOYSA-N 4-[4-(4-chloro-2-methylphenoxy)piperidin-1-yl]-n-(2-chlorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)CC1 HHYBIQJOLMHLOC-UHFFFAOYSA-N 0.000 claims description 3
• IGCXNQLEJAPTMB-UHFFFAOYSA-N 4-[4-(4-chloro-2-methylphenoxy)piperidin-1-yl]-n-(2-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)CC1 IGCXNQLEJAPTMB-UHFFFAOYSA-N 0.000 claims description 3
• OFFJHZRFEDVMAQ-UHFFFAOYSA-N 4-[4-(4-chloro-2-methylphenoxy)piperidin-1-yl]-n-(4-chlorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=CC(Cl)=CC=2)CC1 OFFJHZRFEDVMAQ-UHFFFAOYSA-N 0.000 claims description 3
• IGXXJZSHANKJAD-UHFFFAOYSA-N 4-[4-(4-chloro-2-methylphenoxy)piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=CC(Cl)=CC=2)C)CC1 IGXXJZSHANKJAD-UHFFFAOYSA-N 0.000 claims description 3
• VHUHQRQHGZKQJL-UHFFFAOYSA-N 4-chloro-n-[4-[4-(4-chloro-2-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonylbenzamide Chemical compound CC1=CC(Cl)=CC=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C=2C=CC(Cl)=CC=2)CC1 VHUHQRQHGZKQJL-UHFFFAOYSA-N 0.000 claims description 3
• PQHXPPICWGPBON-IYARVYRRSA-N C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C=2C=CC=CC=2)CC1 Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C=2C=CC=CC=2)CC1 PQHXPPICWGPBON-IYARVYRRSA-N 0.000 claims description 3
• DCPZHBDTBOMBAJ-SAABIXHNSA-N C1=CC(Cl)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 DCPZHBDTBOMBAJ-SAABIXHNSA-N 0.000 claims description 3
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
• PAEZTKREROBBNB-WGSAOQKQSA-N CC1=CC=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 PAEZTKREROBBNB-WGSAOQKQSA-N 0.000 claims description 3
• XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 3
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 3
• 239000007822 coupling agent Substances 0.000 claims description 3
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
• 239000012948 isocyanate Substances 0.000 claims description 3
• 150000002513 isocyanates Chemical class 0.000 claims description 3
• SMIYSQCMVAZNCD-UHFFFAOYSA-N n-(2-bromophenyl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)Br)CC1 SMIYSQCMVAZNCD-UHFFFAOYSA-N 0.000 claims description 3
• INFQIOWPORYTNN-UHFFFAOYSA-N n-(2-chlorophenyl)sulfonyl-4-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound CC1=C(Cl)C=CC(OC2CCN(CC2)C2CCN(CC2)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=C1Cl INFQIOWPORYTNN-UHFFFAOYSA-N 0.000 claims description 3
• OQGRVNBEJUFCBU-UHFFFAOYSA-N n-(2-chlorophenyl)sulfonyl-4-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=CC(Cl)=C(Cl)C(C)=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)CC1 OQGRVNBEJUFCBU-UHFFFAOYSA-N 0.000 claims description 3
• XMLJPFPDQATYIF-UHFFFAOYSA-N n-(4-bromophenyl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=CC(Br)=CC=2)CC1 XMLJPFPDQATYIF-UHFFFAOYSA-N 0.000 claims description 3
• CXBGWBYHXGZMTD-UHFFFAOYSA-N n-(4-bromothiophen-2-yl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2SC=C(Br)C=2)CC1 CXBGWBYHXGZMTD-UHFFFAOYSA-N 0.000 claims description 3
• BGBZPKPXJHATBP-UHFFFAOYSA-N n-(4-chloro-2,5-difluorophenyl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(F)=CC(S(=O)(=O)NC(=O)N2CCC(CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1F BGBZPKPXJHATBP-UHFFFAOYSA-N 0.000 claims description 3
• HBRSFVOYUOMDPA-UHFFFAOYSA-N n-(4-chloro-2,5-dimethylphenyl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(C)=CC(S(=O)(=O)NC(=O)N2CCC(CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1C HBRSFVOYUOMDPA-UHFFFAOYSA-N 0.000 claims description 3
• ZFLFDJDKLXKKDY-UHFFFAOYSA-N n-(5-chloro-2,4-difluorophenyl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(F)=CC(F)=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 ZFLFDJDKLXKKDY-UHFFFAOYSA-N 0.000 claims description 3
• RYOAZTXPWXIRGP-UHFFFAOYSA-N n-(5-chlorothiophen-2-yl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound S1C(Cl)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 RYOAZTXPWXIRGP-UHFFFAOYSA-N 0.000 claims description 3
• MFJWXRIWIGLCGD-UHFFFAOYSA-N n-(benzenesulfonyl)-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=CC=CC=2)CC1 MFJWXRIWIGLCGD-UHFFFAOYSA-N 0.000 claims description 3
• BVFZDVXLSAKDGN-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-1-oxo-2h-isoquinoline-4-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C=2C3=CC=CC=C3C(=O)NC=2)CC1 BVFZDVXLSAKDGN-UHFFFAOYSA-N 0.000 claims description 3
• YRQBSYRJUNLWLK-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 YRQBSYRJUNLWLK-UHFFFAOYSA-N 0.000 claims description 3
• PPPFEIVSKMCULR-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-2-methylpropanamide Chemical compound C1CN(S(=O)(=O)NC(=O)C(C)C)CCC1N1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 PPPFEIVSKMCULR-UHFFFAOYSA-N 0.000 claims description 3
• IVQUMPVXWDQUTI-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-2-phenylacetamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)CC=2C=CC=CC=2)CC1 IVQUMPVXWDQUTI-UHFFFAOYSA-N 0.000 claims description 3
• PFONVERWXQYUJF-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-3-methylsulfonylbenzamide Chemical compound CS(=O)(=O)C1=CC=CC(C(=O)NS(=O)(=O)N2CCC(CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 PFONVERWXQYUJF-UHFFFAOYSA-N 0.000 claims description 3
• OTHSFIWXSYZYEU-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-4-fluorobenzamide Chemical compound C1=CC(F)=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 OTHSFIWXSYZYEU-UHFFFAOYSA-N 0.000 claims description 3
• FMRWQXJQGRYCHJ-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 FMRWQXJQGRYCHJ-UHFFFAOYSA-N 0.000 claims description 3
• TYJQOZIXCKQDQW-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonylcyclohexanecarboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C2CCCCC2)CC1 TYJQOZIXCKQDQW-UHFFFAOYSA-N 0.000 claims description 3
• VSDZDXBYHPHYLG-UHFFFAOYSA-N n-[4-[4-(4-chloro-2-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-3-methylsulfonylbenzamide Chemical compound CC1=CC(Cl)=CC=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C=2C=C(C=CC=2)S(C)(=O)=O)CC1 VSDZDXBYHPHYLG-UHFFFAOYSA-N 0.000 claims description 3
• HWWDVFCLZIAAPG-UHFFFAOYSA-N n-benzoyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NC(=O)C=2C=CC=CC=2)CC1 HWWDVFCLZIAAPG-UHFFFAOYSA-N 0.000 claims description 3
• SHRVEEBUQYOBLS-UHFFFAOYSA-N n-benzylsulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)CC=2C=CC=CC=2)CC1 SHRVEEBUQYOBLS-UHFFFAOYSA-N 0.000 claims description 3
• 229960005141 piperazine Drugs 0.000 claims description 3
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
• 125000001424 substituent group Chemical group 0.000 claims description 3
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
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• HZSIJCWSKQVTBQ-UHFFFAOYSA-N 4-[4-(2,4-dichloro-3-fluorophenoxy)piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=C(F)C(Cl)=CC=2)Cl)CC1 HZSIJCWSKQVTBQ-UHFFFAOYSA-N 0.000 claims description 2
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• 229940095102 methyl benzoate Drugs 0.000 claims description 2
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• DVGHIKBFVGZSDP-UHFFFAOYSA-N n-[4-[4-(2,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonylbenzamide Chemical compound ClC1=CC(Cl)=CC=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C=2C=CC=CC=2)CC1 DVGHIKBFVGZSDP-UHFFFAOYSA-N 0.000 claims description 2
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• SDPQHMHFTWVGGO-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonylbenzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C=2C=CC=CC=2)CC1 SDPQHMHFTWVGGO-UHFFFAOYSA-N 0.000 claims description 2
• 150000002829 nitrogen Chemical group 0.000 claims description 2
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• KIXDEPSHGUXOEE-UHFFFAOYSA-N 4-[4-(5-chloropyridin-2-yl)oxypiperidin-1-yl]-N-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound ClC=1C=CC(=NC=1)OC1CCN(CC1)C1CCN(CC1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)C KIXDEPSHGUXOEE-UHFFFAOYSA-N 0.000 claims 1
• AFCNCARTDLMXEF-UHFFFAOYSA-N N-[4-[4-(4-chloro-2-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonylbenzamide Chemical compound C(C1=CC=CC=C1)(=O)NS(=O)(=O)N1CCC(CC1)N1CCC(CC1)OC1=C(C=C(C=C1)Cl)C AFCNCARTDLMXEF-UHFFFAOYSA-N 0.000 claims 1
• RPKJHDQPAIGBDM-UHFFFAOYSA-N N-[4-[4-[(3,4-dichlorophenyl)methyl]piperidin-1-yl]piperidin-1-yl]sulfonylbenzamide Chemical compound C(C1=CC=CC=C1)(=O)NS(=O)(=O)N1CCC(CC1)N1CCC(CC1)CC1=CC(=C(C=C1)Cl)Cl RPKJHDQPAIGBDM-UHFFFAOYSA-N 0.000 claims 1
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
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