JP5089846B2 - 炎症性疾患を処置するためのモルホリン−アセトアミド誘導体 - Google Patents

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Publication number

JP5089846B2

JP5089846B2 JP2002531106A JP2002531106A JP5089846B2 JP 5089846 B2 JP5089846 B2 JP 5089846B2 JP 2002531106 A JP2002531106 A JP 2002531106A JP 2002531106 A JP2002531106 A JP 2002531106A JP 5089846 B2 JP5089846 B2 JP 5089846B2

Authority

JP

Japan

Prior art keywords

methyl

morpholin

dichlorobenzyl

acetamide

phenyl

Prior art date

2000-09-29

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 - Lifetime

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• 208000027866 inflammatory disease Diseases 0.000 title claims description 7
• BWRNWWSQZROEOA-UHFFFAOYSA-N 2-morpholin-4-ylacetamide Chemical class NC(=O)CN1CCOCC1 BWRNWWSQZROEOA-UHFFFAOYSA-N 0.000 title 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 426
• 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 241
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 173
• 125000000217 alkyl group Chemical group 0.000 claims description 155
• 150000001875 compounds Chemical class 0.000 claims description 141
• -1 2,3-dichlorobenzyl Chemical group 0.000 claims description 126
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 100
• 229910052739 hydrogen Inorganic materials 0.000 claims description 96
• 239000001257 hydrogen Substances 0.000 claims description 96
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 77
• 125000001072 heteroaryl group Chemical group 0.000 claims description 55
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 54
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 54
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 53
• 229910052757 nitrogen Inorganic materials 0.000 claims description 51
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 44
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 44
• 150000003839 salts Chemical class 0.000 claims description 43
• 229910052760 oxygen Inorganic materials 0.000 claims description 41
• 239000001301 oxygen Substances 0.000 claims description 41
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 40
• 125000003118 aryl group Chemical group 0.000 claims description 39
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 37
• 229910052717 sulfur Inorganic materials 0.000 claims description 37
• 239000011593 sulfur Substances 0.000 claims description 37
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 33
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 31
• 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 30
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 27
• 235000019253 formic acid Nutrition 0.000 claims description 27
• 229920006395 saturated elastomer Polymers 0.000 claims description 25
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 22
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• 150000002367 halogens Chemical class 0.000 claims description 21
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 18
• 239000012453 solvate Substances 0.000 claims description 18
• 150000002431 hydrogen Chemical class 0.000 claims description 17
• 208000006673 asthma Diseases 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 16
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 15
• 229910052799 carbon Inorganic materials 0.000 claims description 15
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 15
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 13
• 125000005843 halogen group Chemical group 0.000 claims description 13
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 12
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 12
• 239000005977 Ethylene Substances 0.000 claims description 12
• 125000003342 alkenyl group Chemical group 0.000 claims description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
• 125000005842 heteroatom Chemical group 0.000 claims description 9
• 125000002950 monocyclic group Chemical group 0.000 claims description 9
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
• IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
• 239000002253 acid Substances 0.000 claims description 7
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 7
• 206010039083 rhinitis Diseases 0.000 claims description 7
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 7
• 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• PTUBNTVRWLDJBP-MAUKXSAKSA-N n-[[(2r,5s)-4-[(3,4-dichlorophenyl)methyl]-5-methylmorpholin-2-yl]methyl]-2-phenylacetamide Chemical compound C([C@H]1OC[C@@H](N(C1)CC=1C=C(Cl)C(Cl)=CC=1)C)NC(=O)CC1=CC=CC=C1 PTUBNTVRWLDJBP-MAUKXSAKSA-N 0.000 claims description 4
• ANCDHBXLDURTHN-UHFFFAOYSA-N 2-phenoxypropanamide Chemical compound NC(=O)C(C)OC1=CC=CC=C1 ANCDHBXLDURTHN-UHFFFAOYSA-N 0.000 claims description 3
• KHRWSTKNTPHEIX-UHFFFAOYSA-N n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-2-(2,6-difluorophenyl)acetamide Chemical compound FC1=CC=CC(F)=C1CC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 KHRWSTKNTPHEIX-UHFFFAOYSA-N 0.000 claims description 3
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims 321
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 38
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 28
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 17
• 125000004432 carbon atom Chemical group C* 0.000 claims 13
• 125000000304 alkynyl group Chemical group 0.000 claims 10
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 6
• QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 6
• 125000006317 cyclopropyl amino group Chemical group 0.000 claims 6
• 229940095102 methyl benzoate Drugs 0.000 claims 6
• FGUIUYGIZLOOHE-IBGZPJMESA-N n-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)acetamide Chemical compound C([C@@H](OCC1)CNC(=O)CC=2N=C(OC=2C)C=2C=CC=CC=2)N1CC1=CC=C(Cl)C(Cl)=C1 FGUIUYGIZLOOHE-IBGZPJMESA-N 0.000 claims 4
• AKUWDPJOHNKNMX-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]acetamide Chemical compound ClC1=CC(Cl)=CC=C1CC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 AKUWDPJOHNKNMX-UHFFFAOYSA-N 0.000 claims 3
• JYFNSZDTDYRIHG-UHFFFAOYSA-N 2-(2,5-dichlorophenyl)-n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]acetamide Chemical compound ClC1=CC=C(Cl)C(CC(=O)NCC2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C1 JYFNSZDTDYRIHG-UHFFFAOYSA-N 0.000 claims 3
• JYJSYZYBAVZUHV-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]acetamide Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)CC=2C(=CC=CC=2Cl)Cl)OCC1 JYJSYZYBAVZUHV-UHFFFAOYSA-N 0.000 claims 3
• LZKQBIBTGJUICE-UHFFFAOYSA-N 2-(2-chlorophenyl)-n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]acetamide Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)CC=2C(=CC=CC=2)Cl)OCC1 LZKQBIBTGJUICE-UHFFFAOYSA-N 0.000 claims 3
• UIZQMDGRYJFZQK-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]acetamide Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)CC=2C=C(Cl)C(Cl)=CC=2)OCC1 UIZQMDGRYJFZQK-UHFFFAOYSA-N 0.000 claims 3
• LDDDEDCDPPPQFT-UHFFFAOYSA-N 2-(3-chlorophenyl)-n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]acetamide Chemical compound ClC1=CC=CC(CC(=O)NCC2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C1 LDDDEDCDPPPQFT-UHFFFAOYSA-N 0.000 claims 3
• JHMXPUCRTAYCDZ-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]acetamide Chemical compound C1=CC(Cl)=CC=C1CC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 JHMXPUCRTAYCDZ-UHFFFAOYSA-N 0.000 claims 3
• OUXCRTKKJLVYBY-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]acetamide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(CC(=O)NCC2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C1 OUXCRTKKJLVYBY-UHFFFAOYSA-N 0.000 claims 3
• LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 3
• NHOITSTWCDUYAQ-QFIPXVFZSA-N 3-[2-[[(2s)-4-[(3-chlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]-n-cyclopropylbenzamide Chemical compound ClC1=CC=CC(CN2C[C@H](CNC(=O)CC=3C=C(C=CC=3)C(=O)NC3CC3)OCC2)=C1 NHOITSTWCDUYAQ-QFIPXVFZSA-N 0.000 claims 3
• FTTPPVDVQPABRK-UHFFFAOYSA-N 3-[2-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC(CC(=O)NCC2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C1 FTTPPVDVQPABRK-UHFFFAOYSA-N 0.000 claims 3
• OJQGJGGPRSOVAM-UHFFFAOYSA-N 3-[2-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]-n-ethylbenzamide Chemical compound CCNC(=O)C1=CC=CC(CC(=O)NCC2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C1 OJQGJGGPRSOVAM-UHFFFAOYSA-N 0.000 claims 3
• LJJGPPAFVHTUBZ-UHFFFAOYSA-N 3-[2-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(CC(=O)NCC2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C1 LJJGPPAFVHTUBZ-UHFFFAOYSA-N 0.000 claims 3
• CPTHFDQFZLWHSN-UHFFFAOYSA-N 4-[2-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]-n,n-dimethylbenzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1CC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 CPTHFDQFZLWHSN-UHFFFAOYSA-N 0.000 claims 3
• YIMJPSBXMJBMCH-UHFFFAOYSA-N 4-[2-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]-n-ethylbenzamide Chemical compound C1=CC(C(=O)NCC)=CC=C1CC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 YIMJPSBXMJBMCH-UHFFFAOYSA-N 0.000 claims 3
• RBCYAHOMYPCVHJ-UHFFFAOYSA-N 4-[2-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1CC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 RBCYAHOMYPCVHJ-UHFFFAOYSA-N 0.000 claims 3
• UVGVPEKRWGKGKZ-UHFFFAOYSA-N 4-[2-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]-n-propan-2-ylbenzamide Chemical compound C1=CC(C(=O)NC(C)C)=CC=C1CC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 UVGVPEKRWGKGKZ-UHFFFAOYSA-N 0.000 claims 3
• QAAZDCGSSWACNU-UHFFFAOYSA-N 4-[2-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1CC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 QAAZDCGSSWACNU-UHFFFAOYSA-N 0.000 claims 3
• PTUBNTVRWLDJBP-CRAIPNDOSA-N ClC=1C=C(CN2C[C@H](OC[C@H]2C)CNC(CC2=CC=CC=C2)=O)C=CC=1Cl Chemical compound ClC=1C=C(CN2C[C@H](OC[C@H]2C)CNC(CC2=CC=CC=C2)=O)C=CC=1Cl PTUBNTVRWLDJBP-CRAIPNDOSA-N 0.000 claims 3
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 3
• PIZQTSMNGFLAOU-UHFFFAOYSA-N n-[3-[2-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]phenyl]-2-methylpropanamide Chemical compound CC(C)C(=O)NC1=CC=CC(CC(=O)NCC2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C1 PIZQTSMNGFLAOU-UHFFFAOYSA-N 0.000 claims 3
• IXFWJWZFPVVHBE-UHFFFAOYSA-N n-[4-[2-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]phenyl]-2-methylpropanamide Chemical compound C1=CC(NC(=O)C(C)C)=CC=C1CC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 IXFWJWZFPVVHBE-UHFFFAOYSA-N 0.000 claims 3
• MIJQXFRSAOOOTI-QGZVFWFLSA-N n-[[(2r)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-2-(4-methylsulfonylphenyl)acetamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CC(=O)NC[C@H]1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 MIJQXFRSAOOOTI-QGZVFWFLSA-N 0.000 claims 3
• MIJQXFRSAOOOTI-KRWDZBQOSA-N n-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-2-(4-methylsulfonylphenyl)acetamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CC(=O)NC[C@@H]1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 MIJQXFRSAOOOTI-KRWDZBQOSA-N 0.000 claims 3
• IHTMDVDZFSXHBH-BEFAXECRSA-N n-[[(2s,5r)-4-[(2,5-dichlorophenyl)methyl]-5-methylmorpholin-2-yl]methyl]-2-phenylacetamide Chemical compound C([C@@H]1OC[C@H](N(C1)CC=1C(=CC=C(Cl)C=1)Cl)C)NC(=O)CC1=CC=CC=C1 IHTMDVDZFSXHBH-BEFAXECRSA-N 0.000 claims 3
• PTUBNTVRWLDJBP-QAPCUYQASA-N n-[[(2s,5r)-4-[(3,4-dichlorophenyl)methyl]-5-methylmorpholin-2-yl]methyl]-2-phenylacetamide Chemical compound C([C@@H]1OC[C@H](N(C1)CC=1C=C(Cl)C(Cl)=CC=1)C)NC(=O)CC1=CC=CC=C1 PTUBNTVRWLDJBP-QAPCUYQASA-N 0.000 claims 3
• FCLWTLISXFHQEU-UHFFFAOYSA-N n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-2-(3,4-difluorophenyl)acetamide Chemical compound C1=C(F)C(F)=CC=C1CC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 FCLWTLISXFHQEU-UHFFFAOYSA-N 0.000 claims 3
• ROLSNQHXWUPMFL-UHFFFAOYSA-N n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-2-(3-fluorophenyl)acetamide Chemical compound FC1=CC=CC(CC(=O)NCC2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C1 ROLSNQHXWUPMFL-UHFFFAOYSA-N 0.000 claims 3
• IZOYGZNMKXARJZ-UHFFFAOYSA-N n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-2-(3-nitrophenyl)acetamide Chemical compound [O-][N+](=O)C1=CC=CC(CC(=O)NCC2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C1 IZOYGZNMKXARJZ-UHFFFAOYSA-N 0.000 claims 3
• DNZXWUUNTDBKFN-UHFFFAOYSA-N n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-2-(4-fluoro-2-methylphenyl)acetamide Chemical compound CC1=CC(F)=CC=C1CC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 DNZXWUUNTDBKFN-UHFFFAOYSA-N 0.000 claims 3
• QSVIELROKCBLGE-UHFFFAOYSA-N n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-2-(4-fluorophenyl)acetamide Chemical compound C1=CC(F)=CC=C1CC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 QSVIELROKCBLGE-UHFFFAOYSA-N 0.000 claims 3
• FWZOQJCUPXLSIO-UHFFFAOYSA-N n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-2-(4-methoxyphenyl)acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 FWZOQJCUPXLSIO-UHFFFAOYSA-N 0.000 claims 3
• KZFUBTRBLPLQIJ-UHFFFAOYSA-N n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-2-(4-methylsulfanylphenyl)acetamide Chemical compound C1=CC(SC)=CC=C1CC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 KZFUBTRBLPLQIJ-UHFFFAOYSA-N 0.000 claims 3
• FRZLJHUTGANTLG-UHFFFAOYSA-N n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-2-(4-nitrophenyl)acetamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1CC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 FRZLJHUTGANTLG-UHFFFAOYSA-N 0.000 claims 3
• UBCKTDOUXCDSSM-UHFFFAOYSA-N n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-2-[3-(methanesulfonamido)phenyl]acetamide Chemical compound CS(=O)(=O)NC1=CC=CC(CC(=O)NCC2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C1 UBCKTDOUXCDSSM-UHFFFAOYSA-N 0.000 claims 3
• XOUDBQNDBJIUDX-UHFFFAOYSA-N n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-2-[3-[methyl(methylsulfonyl)amino]phenyl]acetamide Chemical compound CS(=O)(=O)N(C)C1=CC=CC(CC(=O)NCC2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C1 XOUDBQNDBJIUDX-UHFFFAOYSA-N 0.000 claims 3
• AXAYMEOPQHXZBZ-UHFFFAOYSA-N n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-2-[4-(trifluoromethyl)phenyl]acetamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 AXAYMEOPQHXZBZ-UHFFFAOYSA-N 0.000 claims 3
• HMCGXXKIOWCREI-UHFFFAOYSA-N n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-2-phenylacetamide Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)CC=2C=CC=CC=2)OCC1 HMCGXXKIOWCREI-UHFFFAOYSA-N 0.000 claims 3
• CVXRGDUVLQHQIF-UHFFFAOYSA-N n-[[4-[(3-fluorophenyl)methyl]morpholin-2-yl]methyl]-2-[4-(methanesulfonamido)phenyl]acetamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1CC(=O)NCC1OCCN(CC=2C=C(F)C=CC=2)C1 CVXRGDUVLQHQIF-UHFFFAOYSA-N 0.000 claims 3
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