JP2004509952A5 - - Google Patents
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- Publication number
- JP2004509952A5 JP2004509952A5 JP2002531106A JP2002531106A JP2004509952A5 JP 2004509952 A5 JP2004509952 A5 JP 2004509952A5 JP 2002531106 A JP2002531106 A JP 2002531106A JP 2002531106 A JP2002531106 A JP 2002531106A JP 2004509952 A5 JP2004509952 A5 JP 2004509952A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- morpholin
- acetamide
- dichlorobenzyl
- phenyl
- Prior art date
- 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.)
- Granted
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 149
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 141
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 description 103
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 50
- -1 NR13 Chemical compound 0.000 description 37
- 150000001875 compounds Chemical class 0.000 description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 26
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 11
- 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 8
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 6
- 235000019253 formic acid Nutrition 0.000 description 6
- 239000012453 solvate Substances 0.000 description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000007790 solid phase Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000006317 cyclopropyl amino group Chemical group 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 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 description 1
- 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 description 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 description 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 description 1
- 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 description 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 description 1
- 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 description 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 description 1
- 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 description 1
- WISMQAZNLJWJDU-NRFANRHFSA-N 2-[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]-n-[[(2s)-4-[2-(4-fluorophenyl)-2-oxoethyl]morpholin-2-yl]methyl]acetamide Chemical compound C([C@@H](OCC1)CNC(=O)CC=2N=C(OC=2C)C=2C=CC(F)=CC=2)N1CC(=O)C1=CC=C(F)C=C1 WISMQAZNLJWJDU-NRFANRHFSA-N 0.000 description 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 description 1
- ANCDHBXLDURTHN-UHFFFAOYSA-N 2-phenoxypropanamide Chemical compound NC(=O)C(C)OC1=CC=CC=C1 ANCDHBXLDURTHN-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 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 description 1
- 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 description 1
- 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 description 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 description 1
- HWXSNLXRQOVRFJ-UHFFFAOYSA-N 3-[2-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]benzotriazole-5-carboxylic acid Chemical compound C12=CC(C(=O)O)=CC=C2N=NN1CC(=O)NCC(OCC1)CN1CC1=CC=C(Cl)C(Cl)=C1 HWXSNLXRQOVRFJ-UHFFFAOYSA-N 0.000 description 1
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 description 1
- 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 description 1
- 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 description 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 description 1
- 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 description 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 description 1
- XJCCVBPRDUAFBK-NRFANRHFSA-N 4-[4-[2-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]-5-methyl-1,3-oxazol-2-yl]-n,n-dimethylbenzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1C1=NC(CC(=O)NC[C@@H]2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C(C)O1 XJCCVBPRDUAFBK-NRFANRHFSA-N 0.000 description 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 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CODAIKLZEIPJNA-UHFFFAOYSA-N N-(5-phenyltetrazol-2-yl)acetamide Chemical compound C(C)(=O)NN1N=C(N=N1)C1=CC=CC=C1 CODAIKLZEIPJNA-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 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 description 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 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 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 description 1
- 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 description 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 description 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 description 1
- 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 description 1
- 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 description 1
- LHEXVCZVAZHCCT-IBGZPJMESA-N n-[[(2s)-4-(2,1,3-benzoxadiazol-5-ylmethyl)morpholin-2-yl]methyl]-2-[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]acetamide Chemical compound N=1C(CC(=O)NC[C@@H]2OCCN(CC3=CC4=NON=C4C=C3)C2)=C(C)OC=1C1=CC=C(F)C=C1 LHEXVCZVAZHCCT-IBGZPJMESA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- DXUSLRXHNWADRT-AWEZNQCLSA-N n-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]pentanamide Chemical compound C1CO[C@@H](CNC(=O)CCCC)CN1CC1=CC=C(Cl)C(Cl)=C1 DXUSLRXHNWADRT-AWEZNQCLSA-N 0.000 description 1
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-
2001
- 2001-09-28 BR BR0114323-9A patent/BR0114323A/pt not_active IP Right Cessation
- 2001-09-28 WO PCT/GB2001/004345 patent/WO2002026722A1/en not_active Ceased
- 2001-09-28 AU AU2001290143A patent/AU2001290143A1/en not_active Abandoned
- 2001-09-28 NZ NZ525056A patent/NZ525056A/en unknown
- 2001-09-28 CA CA002423251A patent/CA2423251A1/en not_active Abandoned
- 2001-09-28 PL PL01362711A patent/PL362711A1/xx not_active Application Discontinuation
- 2001-09-28 CN CNA018196365A patent/CN1678594A/zh active Pending
- 2001-09-28 US US10/381,767 patent/US7101882B2/en not_active Expired - Lifetime
- 2001-09-28 EP EP01970023.6A patent/EP1324990B1/en not_active Expired - Lifetime
- 2001-09-28 AR ARP010104602A patent/AR035205A1/es not_active Application Discontinuation
- 2001-09-28 KR KR10-2003-7004594A patent/KR20030031198A/ko not_active Withdrawn
- 2001-09-28 JP JP2002531106A patent/JP5089846B2/ja not_active Expired - Lifetime
- 2001-09-28 ES ES01970023.6T patent/ES2527688T3/es not_active Expired - Lifetime
- 2001-09-28 IL IL15509301A patent/IL155093A0/xx unknown
- 2001-09-28 HU HU0302302A patent/HUP0302302A2/hu unknown
- 2001-09-28 CZ CZ20031195A patent/CZ20031195A3/cs unknown
- 2001-09-28 MX MXPA03002814A patent/MXPA03002814A/es unknown
-
2003
- 2003-03-27 US US10/509,519 patent/US20050222147A1/en not_active Abandoned
- 2003-03-28 NO NO20031442A patent/NO20031442L/no unknown
-
2005
- 2005-11-22 US US11/284,544 patent/US7560548B2/en not_active Expired - Lifetime
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2009
- 2009-02-24 US US12/391,855 patent/US20090163495A1/en not_active Abandoned
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