CZ20031195A3 - Morfolinacetamidové deriváty - Google Patents

Info

Publication number

CZ20031195A3

CZ20031195A3 CZ20031195A CZ20031195A CZ20031195A3 CZ 20031195 A3 CZ20031195 A3 CZ 20031195A3 CZ 20031195 A CZ20031195 A CZ 20031195A CZ 20031195 A CZ20031195 A CZ 20031195A CZ 20031195 A3 CZ20031195 A3 CZ 20031195A3

Authority

CZ

Czechia

Prior art keywords

methyl

morpholin

acetamide

dichlorobenzyl

phenyl

Prior art date

2000-09-29

Links

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• BWRNWWSQZROEOA-UHFFFAOYSA-N 2-morpholin-4-ylacetamide Chemical class NC(=O)CN1CCOCC1 BWRNWWSQZROEOA-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 276
• 239000000203 mixture Substances 0.000 claims abstract description 182
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 103
• 238000000034 method Methods 0.000 claims abstract description 48
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 47
• 239000001257 hydrogen Substances 0.000 claims abstract description 47
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 37
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 19
• 230000008569 process Effects 0.000 claims abstract description 18
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 17
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 12
• 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 10
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 8
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 7
• 239000005977 Ethylene Substances 0.000 claims abstract description 7
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 6
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 6
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 227
• 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 172
• -1 {4 - [(5-chlorothien-2-yl) methyl] morpholin-2-yl} methyl Chemical group 0.000 claims description 161
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 147
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 81
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 64
• 125000001072 heteroaryl group Chemical group 0.000 claims description 45
• 125000003118 aryl group Chemical group 0.000 claims description 36
• BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 33
• 229910052757 nitrogen Inorganic materials 0.000 claims description 29
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 29
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 26
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 25
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
• 229920005989 resin Polymers 0.000 claims description 22
• 239000011347 resin Substances 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 20
• 229920006395 saturated elastomer Polymers 0.000 claims description 20
• 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 19
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 19
• 150000003839 salts Chemical class 0.000 claims description 19
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
• 238000002360 preparation method Methods 0.000 claims description 18
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
• ZMANZCXQSJIPKH-UHFFFAOYSA-N N,N-Diethylethanamine Substances CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 17
• 229910052736 halogen Inorganic materials 0.000 claims description 17
• 150000002367 halogens Chemical class 0.000 claims description 17
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 17
• 229910052717 sulfur Inorganic materials 0.000 claims description 17
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 16
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 14
• 208000006673 asthma Diseases 0.000 claims description 14
• 235000019253 formic acid Nutrition 0.000 claims description 14
• 239000012453 solvate Substances 0.000 claims description 14
• 201000010099 disease Diseases 0.000 claims description 13
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 13
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 13
• 125000006239 protecting group Chemical group 0.000 claims description 13
• 125000004434 sulfur atom Chemical group 0.000 claims description 13
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 11
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 10
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 10
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 8
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 8
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
• 125000005843 halogen group Chemical group 0.000 claims description 8
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
• 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 7
• 238000006243 chemical reaction Methods 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 239000001301 oxygen Substances 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 7
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 6
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
• 229910052794 bromium Inorganic materials 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 6
• 230000002757 inflammatory effect Effects 0.000 claims description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 6
• 239000007790 solid phase Substances 0.000 claims description 5
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
• 125000006317 cyclopropyl amino group Chemical group 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• 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 4
• 239000011593 sulfur Substances 0.000 claims description 4
• 150000002391 heterocyclic compounds Chemical class 0.000 claims description 3
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 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 description 2
• QFRPHXOFNBDLKV-SFHVURJKSA-N 2-[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]-n-[[(2s)-4-(2-methylprop-2-enyl)morpholin-2-yl]methyl]acetamide Chemical compound C1N(CC(=C)C)CCO[C@H]1CNC(=O)CC1=C(C)OC(C=2C=CC(F)=CC=2)=N1 QFRPHXOFNBDLKV-SFHVURJKSA-N 0.000 claims description 2
• 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 2
• 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 2
• 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 2
• 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 2
• 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 2
• OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims description 2
• IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 2
• 239000000969 carrier Substances 0.000 claims description 2
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 2
• 239000003085 diluting agent Substances 0.000 claims description 2
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
• 150000002466 imines Chemical class 0.000 claims description 2
• 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 2
• 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 2
• 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 2
• 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 description 2
• 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 description 2
• 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 description 2
• RKNZXYVPBNPYLD-FQEVSTJZSA-N n-cyclopropyl-3-[2-[[(2s)-4-[(3,4-difluorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]benzamide Chemical compound C1=C(F)C(F)=CC=C1CN1C[C@H](CNC(=O)CC=2C=C(C=CC=2)C(=O)NC2CC2)OCC1 RKNZXYVPBNPYLD-FQEVSTJZSA-N 0.000 claims description 2
• 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 claims description 2
• 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 2
• 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 claims 1
• KPPVNWGJXFMGAM-UUILKARUSA-N (e)-2-methyl-1-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)but-2-en-1-one Chemical compound CC1=CC=C2N(C(=O)C(/C)=C/C)CCCC2=C1 KPPVNWGJXFMGAM-UUILKARUSA-N 0.000 claims 1
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 1
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
• ROBASCRROMVVND-SFHVURJKSA-N 3-[2-[[(2s)-4-[(5-chlorothiophen-2-yl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]-n-cyclopropylbenzamide Chemical compound S1C(Cl)=CC=C1CN1C[C@H](CNC(=O)CC=2C=C(C=CC=2)C(=O)NC2CC2)OCC1 ROBASCRROMVVND-SFHVURJKSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 125000000304 alkynyl group Chemical group 0.000 claims 1
• 125000004429 atom Chemical group 0.000 claims 1
• DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• MOVDZSAHDZYDQG-UHFFFAOYSA-N methyl 3-[2-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]benzotriazole-5-carboxylate Chemical compound C12=CC(C(=O)OC)=CC=C2N=NN1CC(=O)NCC(OCC1)CN1CC1=CC=C(Cl)C(Cl)=C1 MOVDZSAHDZYDQG-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
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