PT2066659E - Derivados de sulfonamida substituídos - Google Patents

Info

Publication number

PT2066659E

PT2066659E PT78185006T PT07818500T PT2066659E PT 2066659 E PT2066659 E PT 2066659E PT 78185006 T PT78185006 T PT 78185006T PT 07818500 T PT07818500 T PT 07818500T PT 2066659 E PT2066659 E PT 2066659E

Authority

PT

Portugal

Prior art keywords

methoxy

ethanone

piperidin

piperazin

pyrrolidin

Prior art date

2006-09-29

Links

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• 150000003456 sulfonamides Chemical class 0.000 title claims abstract description 35
• 229940124530 sulfonamide Drugs 0.000 title claims abstract description 31
• -1 aminocarbonyl-methoxyethyl groups Chemical group 0.000 claims abstract description 572
• 239000000203 mixture Substances 0.000 claims abstract description 122
• 125000003118 aryl group Chemical group 0.000 claims abstract description 57
• 229920006395 saturated elastomer Polymers 0.000 claims abstract description 46
• 239000002253 acid Substances 0.000 claims abstract description 41
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 41
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 29
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 18
• 239000003814 drug Substances 0.000 claims abstract description 17
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 17
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 16
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 14
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 14
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 10
• 238000004519 manufacturing process Methods 0.000 claims abstract description 9
• 150000003839 salts Chemical class 0.000 claims abstract description 9
• 150000007513 acids Chemical class 0.000 claims abstract description 7
• 239000004480 active ingredient Substances 0.000 claims abstract description 4
• 239000000654 additive Substances 0.000 claims abstract description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 318
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 165
• 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims description 70
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 59
• 150000003254 radicals Chemical group 0.000 claims description 49
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 39
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 36
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 27
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 24
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 23
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 22
• 229910052794 bromium Inorganic materials 0.000 claims description 22
• 238000011282 treatment Methods 0.000 claims description 22
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
• 229910052739 hydrogen Inorganic materials 0.000 claims description 15
• HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical class O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 claims description 14
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 13
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 13
• 208000002193 Pain Diseases 0.000 claims description 13
• ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 11
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
• QPMLSUSACCOBDK-UHFFFAOYSA-N diazepane Chemical compound C1CCNNCC1 QPMLSUSACCOBDK-UHFFFAOYSA-N 0.000 claims description 8
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 125000001544 thienyl group Chemical group 0.000 claims description 8
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 201000010099 disease Diseases 0.000 claims description 7
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 7
• 125000002541 furyl group Chemical group 0.000 claims description 6
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
• MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 5
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 4
• 208000000094 Chronic Pain Diseases 0.000 claims description 4
• WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 4
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
• 208000008589 Obesity Diseases 0.000 claims description 4
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
• 206010040070 Septic Shock Diseases 0.000 claims description 4
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 4
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 208000004296 neuralgia Diseases 0.000 claims description 4
• 208000021722 neuropathic pain Diseases 0.000 claims description 4
• 235000020824 obesity Nutrition 0.000 claims description 4
• 125000003386 piperidinyl group Chemical group 0.000 claims description 4
• 230000036303 septic shock Effects 0.000 claims description 4
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• SQENTLPYJNQWPR-UHFFFAOYSA-N Cl.Cl.Cl.Cl.C(C)=O Chemical compound Cl.Cl.Cl.Cl.C(C)=O SQENTLPYJNQWPR-UHFFFAOYSA-N 0.000 claims description 3
• 206010061218 Inflammation Diseases 0.000 claims description 3
• 208000012902 Nervous system disease Diseases 0.000 claims description 3
• 208000025966 Neurological disease Diseases 0.000 claims description 3
• BXOBQDOEBJELFC-UHFFFAOYSA-N acetaldehyde;dihydrochloride Chemical compound Cl.Cl.CC=O BXOBQDOEBJELFC-UHFFFAOYSA-N 0.000 claims description 3
• 230000001154 acute effect Effects 0.000 claims description 3
• 208000005298 acute pain Diseases 0.000 claims description 3
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
• 230000004054 inflammatory process Effects 0.000 claims description 3
• 125000005936 piperidyl group Chemical group 0.000 claims description 3
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
• 208000009935 visceral pain Diseases 0.000 claims description 3
• SFRRCJIATFQRAU-UHFFFAOYSA-N 1-(4-benzylpiperazin-1-yl)-2-[[1-(2,6-dichlorophenyl)sulfonylpiperidin-2-yl]methoxy]ethanone Chemical compound ClC1=CC=CC(Cl)=C1S(=O)(=O)N1C(COCC(=O)N2CCN(CC=3C=CC=CC=3)CC2)CCCC1 SFRRCJIATFQRAU-UHFFFAOYSA-N 0.000 claims description 2
• MTDJYBHLNVJDKT-UHFFFAOYSA-N 1-[2-(5-bromopyridin-3-yl)piperidin-1-yl]-2-[[1-[3-(trifluoromethyl)phenyl]sulfonylpiperidin-2-yl]methoxy]ethanone Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)N2C(CCCC2)COCC(=O)N2C(CCCC2)C=2C=C(Br)C=NC=2)=C1 MTDJYBHLNVJDKT-UHFFFAOYSA-N 0.000 claims description 2
• UWVZRKJCJDZAHZ-UHFFFAOYSA-N 1-[4-(3,5-dimethoxyphenyl)piperazin-1-yl]-2-[[1-(4-methoxy-2,6-dimethylphenyl)sulfonylpyrrolidin-2-yl]methoxy]ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(COCC(=O)N2CCN(CC2)C=2C=C(OC)C=C(OC)C=2)CCC1 UWVZRKJCJDZAHZ-UHFFFAOYSA-N 0.000 claims description 2
• HWAUSIFSYKFJRL-UHFFFAOYSA-N 1-[4-(3-methoxyphenyl)piperazin-1-yl]ethanone Chemical compound COC1=CC=CC(N2CCN(CC2)C(C)=O)=C1 HWAUSIFSYKFJRL-UHFFFAOYSA-N 0.000 claims description 2
• NZRPPZMMHAPCNW-UHFFFAOYSA-N 1-[4-(4-methoxyphenyl)piperazin-1-yl]-2-[[1-(2,4,6-trichlorophenyl)sulfonylpyrrolidin-2-yl]methoxy]ethanone Chemical compound C1=CC(OC)=CC=C1N1CCN(C(=O)COCC2N(CCC2)S(=O)(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)CC1 NZRPPZMMHAPCNW-UHFFFAOYSA-N 0.000 claims description 2
• AZDXOXWFGNQSPC-UHFFFAOYSA-N 2-(piperidin-1-ylmethyl)morpholine Chemical compound C1CCCCN1CC1CNCCO1 AZDXOXWFGNQSPC-UHFFFAOYSA-N 0.000 claims description 2
• KUNOECHYRSAZOR-UHFFFAOYSA-N 2-[[1-(1-benzothiophen-3-ylsulfonyl)piperidin-2-yl]methoxy]-1-[4-(1-methylpiperidin-4-yl)piperazin-1-yl]ethanone Chemical compound C1CN(C)CCC1N1CCN(C(=O)COCC2N(CCCC2)S(=O)(=O)C=2C3=CC=CC=C3SC=2)CC1 KUNOECHYRSAZOR-UHFFFAOYSA-N 0.000 claims description 2
• LVGAVVPJUDXUEA-UHFFFAOYSA-N 2-[[1-(2,6-dichlorophenyl)sulfonylpiperidin-2-yl]methoxy]-1-(2-pyridin-3-ylpyrrolidin-1-yl)ethanone Chemical compound ClC1=CC=CC(Cl)=C1S(=O)(=O)N1C(COCC(=O)N2C(CCC2)C=2C=NC=CC=2)CCCC1 LVGAVVPJUDXUEA-UHFFFAOYSA-N 0.000 claims description 2
• OACYPNOMTJCOIL-UHFFFAOYSA-N 2-[[1-(2,6-dichlorophenyl)sulfonylpiperidin-2-yl]methoxy]-1-[2-[(4,6-dimethylpyridin-2-yl)methyl]pyrrolidin-1-yl]ethanone Chemical compound CC1=CC(C)=NC(CC2N(CCC2)C(=O)COCC2N(CCCC2)S(=O)(=O)C=2C(=CC=CC=2Cl)Cl)=C1 OACYPNOMTJCOIL-UHFFFAOYSA-N 0.000 claims description 2
• LAOQNIXJKBRRGO-UHFFFAOYSA-N 2-[[1-(2,6-dichlorophenyl)sulfonylpiperidin-2-yl]methoxy]-1-[2-[4-(dimethylamino)phenyl]pyrrolidin-1-yl]ethanone Chemical compound C1=CC(N(C)C)=CC=C1C1N(C(=O)COCC2N(CCCC2)S(=O)(=O)C=2C(=CC=CC=2Cl)Cl)CCC1 LAOQNIXJKBRRGO-UHFFFAOYSA-N 0.000 claims description 2
• XIFFKZLEMPJMIO-UHFFFAOYSA-N 2-[[1-(4-methoxy-2,6-dimethylphenyl)sulfonylpiperidin-2-yl]methoxy]-1-(4-methyl-1,4-diazepan-1-yl)ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(COCC(=O)N2CCN(C)CCC2)CCCC1 XIFFKZLEMPJMIO-UHFFFAOYSA-N 0.000 claims description 2
• KLQDJZKFAIJFSQ-UHFFFAOYSA-N 2-[[1-(4-methoxy-2,6-dimethylphenyl)sulfonylpyrrolidin-2-yl]methoxy]-1-[4-(2-pyrrolidin-1-ylethyl)piperidin-1-yl]ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(COCC(=O)N2CCC(CCN3CCCC3)CC2)CCC1 KLQDJZKFAIJFSQ-UHFFFAOYSA-N 0.000 claims description 2
• NKUPNJVGUPAMEB-UHFFFAOYSA-N 3-[4-[2-[[1-(4-methoxy-2,6-dimethylphenyl)sulfonylpiperidin-2-yl]methoxy]acetyl]piperazin-1-yl]propanenitrile Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(COCC(=O)N2CCN(CCC#N)CC2)CCCC1 NKUPNJVGUPAMEB-UHFFFAOYSA-N 0.000 claims description 2
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
• GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 2
• 206010019233 Headaches Diseases 0.000 claims description 2
• 208000019695 Migraine disease Diseases 0.000 claims description 2
• 206010063837 Reperfusion injury Diseases 0.000 claims description 2
• 206010012601 diabetes mellitus Diseases 0.000 claims description 2
• 231100000869 headache Toxicity 0.000 claims description 2
• 239000003112 inhibitor Substances 0.000 claims description 2
• 230000002981 neuropathic effect Effects 0.000 claims description 2
• FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 2
• 208000023504 respiratory system disease Diseases 0.000 claims description 2
• 230000009278 visceral effect Effects 0.000 claims description 2
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 3
• 125000005605 benzo group Chemical group 0.000 claims 3
• DQXQUKDSAZJXCW-UHFFFAOYSA-N 1-[4-(2-phenylethyl)piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CCC1=CC=CC=C1 DQXQUKDSAZJXCW-UHFFFAOYSA-N 0.000 claims 2
• AVCQLYXAEKNILW-UHFFFAOYSA-N 1-[4-(4-methoxyphenyl)piperazin-1-yl]ethanone Chemical compound C1=CC(OC)=CC=C1N1CCN(C(C)=O)CC1 AVCQLYXAEKNILW-UHFFFAOYSA-N 0.000 claims 2
• MGJTXSWKPWFOSV-UHFFFAOYSA-N 1-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]ethanone Chemical compound C1CN(C)CCN1C1CCN(C(C)=O)CC1 MGJTXSWKPWFOSV-UHFFFAOYSA-N 0.000 claims 2
• FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims 1
• NQGFJWAVGAGVQF-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)sulfonylpiperidine Chemical compound ClC1=CC=CC(Cl)=C1S(=O)(=O)N1CCCCC1 NQGFJWAVGAGVQF-UHFFFAOYSA-N 0.000 claims 1
• VHAUCVJHIHPFAN-UHFFFAOYSA-N 1-(3-pyridin-3-ylpyrrolidin-1-yl)-2-[[1-(2,4,6-trichlorophenyl)sulfonylpiperidin-2-yl]methoxy]ethanone Chemical compound ClC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)N1C(COCC(=O)N2CC(CC2)C=2C=NC=CC=2)CCCC1 VHAUCVJHIHPFAN-UHFFFAOYSA-N 0.000 claims 1
• OVUXTRAZRQORKY-UHFFFAOYSA-N 1-(4-benzylpiperazin-1-yl)-2-[[1-(2,5-dichlorothiophen-3-yl)sulfonylpyrrolidin-2-yl]methoxy]ethanone Chemical compound S1C(Cl)=CC(S(=O)(=O)N2C(CCC2)COCC(=O)N2CCN(CC=3C=CC=CC=3)CC2)=C1Cl OVUXTRAZRQORKY-UHFFFAOYSA-N 0.000 claims 1
• DUIMATYBNXNRMU-UHFFFAOYSA-N 1-(4-pyridin-4-ylpiperazin-1-yl)ethanone Chemical compound C1CN(C(=O)C)CCN1C1=CC=NC=C1 DUIMATYBNXNRMU-UHFFFAOYSA-N 0.000 claims 1
• SKJVKUHWDKQIRY-UHFFFAOYSA-N 1-(4-pyrrolidin-1-ylpiperidin-1-yl)ethanone Chemical compound C1CN(C(=O)C)CCC1N1CCCC1 SKJVKUHWDKQIRY-UHFFFAOYSA-N 0.000 claims 1
• QNQOWXDUWRCXPB-MRTLOADZSA-N 1-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]-2-[[1-(4-methoxy-2,6-dimethylphenyl)sulfonylpyrrolidin-2-yl]methoxy]ethanone Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(COCC(=O)N2C[C@@H](CC2)N(C)C)CCC1 QNQOWXDUWRCXPB-MRTLOADZSA-N 0.000 claims 1
• SOWQZPBJILIBDL-UHFFFAOYSA-N 1-[2-(6-methoxypyridin-3-yl)piperidin-1-yl]-2-[[1-(2,4,6-trimethylphenyl)sulfonylpiperidin-2-yl]methoxy]ethanone Chemical compound C1=NC(OC)=CC=C1C1N(C(=O)COCC2N(CCCC2)S(=O)(=O)C=2C(=CC(C)=CC=2C)C)CCCC1 SOWQZPBJILIBDL-UHFFFAOYSA-N 0.000 claims 1
• HWQQEGAYPNCAQW-UHFFFAOYSA-N 1-[4-(4-benzyl-1,3-thiazol-2-yl)piperazin-1-yl]-2-[[1-(2,4,6-trimethylphenyl)sulfonylpiperidin-2-yl]methoxy]ethanone Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)N1C(COCC(=O)N2CCN(CC2)C=2SC=C(CC=3C=CC=CC=3)N=2)CCCC1 HWQQEGAYPNCAQW-UHFFFAOYSA-N 0.000 claims 1
• UZEZNYRFOKQIKJ-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C1=CC=C(F)C=C1 UZEZNYRFOKQIKJ-UHFFFAOYSA-N 0.000 claims 1
• FGTMGQCWVZCCGN-UHFFFAOYSA-N 1-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]-2-[[1-(2,4,6-trimethylphenyl)sulfonylpiperidin-2-yl]methoxy]ethanone Chemical compound C1CN(C)CCN1C1CCN(C(=O)COCC2N(CCCC2)S(=O)(=O)C=2C(=CC(C)=CC=2C)C)CC1 FGTMGQCWVZCCGN-UHFFFAOYSA-N 0.000 claims 1
• PQWDROLKDOSWOR-UHFFFAOYSA-N 1-[4-(5-chloro-2-methylphenyl)piperazin-1-yl]-2-[[1-(2,6-dichlorophenyl)sulfonylpiperidin-2-yl]methoxy]ethanone Chemical compound CC1=CC=C(Cl)C=C1N1CCN(C(=O)COCC2N(CCCC2)S(=O)(=O)C=2C(=CC=CC=2Cl)Cl)CC1 PQWDROLKDOSWOR-UHFFFAOYSA-N 0.000 claims 1
• MQEALGADWDWVDX-UHFFFAOYSA-N 1-[4-[(4-bromophenyl)methyl]piperazin-1-yl]-2-[[1-(2,6-dichlorophenyl)sulfonylpyrrolidin-2-yl]methoxy]ethanone Chemical compound ClC1=CC=CC(Cl)=C1S(=O)(=O)N1C(COCC(=O)N2CCN(CC=3C=CC(Br)=CC=3)CC2)CCC1 MQEALGADWDWVDX-UHFFFAOYSA-N 0.000 claims 1
• CRCOOFUBSJMQAQ-UHFFFAOYSA-N 1-[4-[2-[di(propan-2-yl)amino]ethyl]piperazin-1-yl]ethanone Chemical compound CC(C)N(C(C)C)CCN1CCN(C(C)=O)CC1 CRCOOFUBSJMQAQ-UHFFFAOYSA-N 0.000 claims 1
• KIJSDNVYUXPIFU-UHFFFAOYSA-N 1-[4-[5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C1=CC=C(C(F)(F)F)C=N1 KIJSDNVYUXPIFU-UHFFFAOYSA-N 0.000 claims 1
• HYJVAKPUVOTFJS-UHFFFAOYSA-N 2-[2-[1-(4-methoxyphenyl)sulfonylpiperidin-2-yl]ethoxy]-1-[4-(2-phenylethyl)piperazin-1-yl]ethanone Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C(CCOCC(=O)N2CCN(CCC=3C=CC=CC=3)CC2)CCCC1 HYJVAKPUVOTFJS-UHFFFAOYSA-N 0.000 claims 1
• SNDNJDXVHDHFSQ-UHFFFAOYSA-N 2-[4-[2-[[1-(4-methoxy-2,6-dimethylphenyl)sulfonylpiperidin-2-yl]methoxy]acetyl]piperazin-1-yl]pyridine-3-carbonitrile Chemical compound CC1=CC(OC)=CC(C)=C1S(=O)(=O)N1C(COCC(=O)N2CCN(CC2)C=2C(=CC=CN=2)C#N)CCCC1 SNDNJDXVHDHFSQ-UHFFFAOYSA-N 0.000 claims 1
• XFLMBMJDGOISPS-UHFFFAOYSA-N 2-[[1-(2,6-dichlorophenyl)sulfonylpiperidin-2-yl]methoxy]-1-[4-[(2-fluorophenyl)methyl]piperazin-1-yl]ethanone Chemical compound FC1=CC=CC=C1CN1CCN(C(=O)COCC2N(CCCC2)S(=O)(=O)C=2C(=CC=CC=2Cl)Cl)CC1 XFLMBMJDGOISPS-UHFFFAOYSA-N 0.000 claims 1
• VFHVQHSQJKDTJA-UHFFFAOYSA-N 2-[[1-(2,6-dichlorophenyl)sulfonylpiperidin-2-yl]methoxy]-1-[4-[(4-methylphenyl)methyl]piperazin-1-yl]ethanone Chemical compound C1=CC(C)=CC=C1CN1CCN(C(=O)COCC2N(CCCC2)S(=O)(=O)C=2C(=CC=CC=2Cl)Cl)CC1 VFHVQHSQJKDTJA-UHFFFAOYSA-N 0.000 claims 1
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• DZKWUAWRBJHCDA-UHFFFAOYSA-N 2-[[2-(4-methoxy-2,3,6-trimethylphenyl)sulfonyl-3,4-dihydro-1h-isoquinolin-3-yl]methoxy]-1-[4-[(1-methylpiperidin-4-yl)methyl]piperazin-1-yl]ethanone Chemical compound CC1=C(C)C(OC)=CC(C)=C1S(=O)(=O)N1C(COCC(=O)N2CCN(CC3CCN(C)CC3)CC2)CC2=CC=CC=C2C1 DZKWUAWRBJHCDA-UHFFFAOYSA-N 0.000 claims 1
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