ES2527688T3 - Derivados de morfolin-acetamida para el tratamiento de enfermedades inflamatorias - Google Patents

Info

Publication number

ES2527688T3

ES2527688T3 ES01970023.6T ES01970023T ES2527688T3 ES 2527688 T3 ES2527688 T3 ES 2527688T3 ES 01970023 T ES01970023 T ES 01970023T ES 2527688 T3 ES2527688 T3 ES 2527688T3

Authority

ES

Spain

Prior art keywords

methyl

morpholin

acetamide

dichlorobenzyl

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 10
• BWRNWWSQZROEOA-UHFFFAOYSA-N 2-morpholin-4-ylacetamide Chemical class NC(=O)CN1CCOCC1 BWRNWWSQZROEOA-UHFFFAOYSA-N 0.000 title description 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 360
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims abstract description 334
• 150000001875 compounds Chemical class 0.000 claims abstract description 215
• 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims abstract description 210
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims abstract description 90
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 52
• 150000003839 salts Chemical class 0.000 claims abstract description 34
• 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 abstract description 26
• 235000019253 formic acid Nutrition 0.000 claims abstract description 26
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims abstract description 25
• 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 abstract description 4
• 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 abstract description 4
• 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 abstract description 4
• 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 abstract description 4
• 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 abstract description 4
• VZXHCMDYUZPSNQ-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-[[4-[(3,4-dichlorophenyl)methyl]-5,5-dimethylmorpholin-2-yl]methyl]acetamide Chemical compound C1N(CC=2C=C(Cl)C(Cl)=CC=2)C(C)(C)COC1CNC(=O)CC1=CC=C(Cl)C=C1 VZXHCMDYUZPSNQ-UHFFFAOYSA-N 0.000 claims abstract description 4
• 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 abstract description 4
• 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 abstract description 4
• 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 abstract description 4
• 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 abstract 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 abstract description 4
• 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 abstract description 4
• 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 abstract description 4
• 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 abstract description 4
• GLLIZTBQMBJXFI-UHFFFAOYSA-N n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-2-(4-methylphenyl)acetamide Chemical compound C1=CC(C)=CC=C1CC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 GLLIZTBQMBJXFI-UHFFFAOYSA-N 0.000 claims abstract description 4
• 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 abstract description 4
• USILSJUHUPHFFZ-UHFFFAOYSA-N n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-2-(5-methyl-1-phenylpyrazol-4-yl)acetamide Chemical compound C1=NN(C=2C=CC=CC=2)C(C)=C1CC(=O)NCC(OCC1)CN1CC1=CC=C(Cl)C(Cl)=C1 USILSJUHUPHFFZ-UHFFFAOYSA-N 0.000 claims abstract description 4
• FGUIUYGIZLOOHE-UHFFFAOYSA-N n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)acetamide Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CC(=O)NCC(OCC1)CN1CC1=CC=C(Cl)C(Cl)=C1 FGUIUYGIZLOOHE-UHFFFAOYSA-N 0.000 claims abstract description 4
• 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 abstract description 4
• ZRPWFIGWYJCROJ-UHFFFAOYSA-N n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-2-phenoxyacetamide Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)COC=2C=CC=CC=2)OCC1 ZRPWFIGWYJCROJ-UHFFFAOYSA-N 0.000 claims abstract description 4
• 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 abstract description 4
• ZMGHLJFRSADFNU-UHFFFAOYSA-N n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-2-thiophen-3-ylacetamide Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)CC2=CSC=C2)OCC1 ZMGHLJFRSADFNU-UHFFFAOYSA-N 0.000 claims abstract description 4
• PIGPZJQOGGOVGR-UHFFFAOYSA-N n-[[4-[3-(3,4-dichlorophenyl)propyl]morpholin-2-yl]methyl]-2-phenylacetamide Chemical compound C1=C(Cl)C(Cl)=CC=C1CCCN1CC(CNC(=O)CC=2C=CC=CC=2)OCC1 PIGPZJQOGGOVGR-UHFFFAOYSA-N 0.000 claims abstract description 4
• -1 {4 - [(5-chlorothien-2-yl) methyl] morpholin-2-yl} methyl Chemical group 0.000 claims description 164
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 70
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 42
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 28
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 24
• 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 22
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 18
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 18
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 16
• 239000012453 solvate Substances 0.000 claims description 16
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 13
• METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 13
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 12
• 239000002253 acid Substances 0.000 claims description 12
• 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 description 11
• 239000003814 drug Substances 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 6
• 125000006317 cyclopropyl amino group Chemical group 0.000 claims description 6
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 4
• MKCWTWOIIWRROF-UHFFFAOYSA-N 1-[2-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]benzotriazole-5-carboxylic acid Chemical compound OC(=O)c1ccc2n(CC(=O)NCC3CN(Cc4ccc(Cl)c(Cl)c4)CCO3)nnc2c1 MKCWTWOIIWRROF-UHFFFAOYSA-N 0.000 claims description 3
• KQJLAVQBOMJGFC-UHFFFAOYSA-N 2-(4-bromo-3,5-dimethylpyrazol-1-yl)-n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]acetamide Chemical compound CC1=C(Br)C(C)=NN1CC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 KQJLAVQBOMJGFC-UHFFFAOYSA-N 0.000 claims description 3
• UQVDLUQACOPECV-UGNFMNBCSA-N 2-[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]-n-[[(2s)-4-(1-phenylethyl)morpholin-2-yl]methyl]acetamide Chemical compound C([C@@H]1OCCN(C1)C(C)C=1C=CC=CC=1)NC(=O)CC(=C(O1)C)N=C1C1=CC=C(F)C=C1 UQVDLUQACOPECV-UGNFMNBCSA-N 0.000 claims description 3
• CEOMCIZJEQMSPD-UHFFFAOYSA-N 2-cyclohexyl-n-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]acetamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)CC2CCCCC2)OCC1 CEOMCIZJEQMSPD-UHFFFAOYSA-N 0.000 claims description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 3
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 claims description 3
• HFUNQLVTMBETML-UHFFFAOYSA-N methyl 2-[2-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]benzotriazole-5-carboxylate Chemical compound N1=C2C=C(C(=O)OC)C=CC2=NN1CC(=O)NCC(OCC1)CN1CC1=CC=C(Cl)C(Cl)=C1 HFUNQLVTMBETML-UHFFFAOYSA-N 0.000 claims description 3
• BTLXBJBBTNKZOW-UHFFFAOYSA-N methyl 3-[2-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]benzoate Chemical compound COC(=O)C1=CC=CC(CC(=O)NCC2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C1 BTLXBJBBTNKZOW-UHFFFAOYSA-N 0.000 claims description 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 description 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 description 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 description 3
• FGUIUYGIZLOOHE-LJQANCHMSA-N n-[[(2r)-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-LJQANCHMSA-N 0.000 claims description 3
• VOSAXWZFOHNAKO-MRXNPFEDSA-N n-[[(2r)-4-[(5-chlorothiophen-2-yl)methyl]morpholin-2-yl]methyl]-2-[3-(methanesulfonamido)phenyl]acetamide Chemical compound CS(=O)(=O)NC1=CC=CC(CC(=O)NC[C@H]2OCCN(CC=3SC(Cl)=CC=3)C2)=C1 VOSAXWZFOHNAKO-MRXNPFEDSA-N 0.000 claims description 3
• HBMKGJJZOMSKFC-SFHVURJKSA-N n-[[(2s)-4-(3,4-dichlorobenzoyl)morpholin-2-yl]methyl]-2-[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]acetamide Chemical compound C([C@@H](OCC1)CNC(=O)CC=2N=C(OC=2C)C=2C=CC(F)=CC=2)N1C(=O)C1=CC=C(Cl)C(Cl)=C1 HBMKGJJZOMSKFC-SFHVURJKSA-N 0.000 claims description 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 description 3
• IRPHGDKGHNCXIA-HNNXBMFYSA-N n-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-4-methylpentanamide Chemical compound C1CO[C@@H](CNC(=O)CCC(C)C)CN1CC1=CC=C(Cl)C(Cl)=C1 IRPHGDKGHNCXIA-HNNXBMFYSA-N 0.000 claims description 3
• STEXWNBVZFVLID-ZDUSSCGKSA-N n-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]cyclopropanecarboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1C[C@H](CNC(=O)C2CC2)OCC1 STEXWNBVZFVLID-ZDUSSCGKSA-N 0.000 claims description 3
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