AU2002350366A1 - Pyrrolidone carboxamides - Google Patents

Info

Publication number

AU2002350366A1

AU2002350366A1 AU2002350366A AU2002350366A AU2002350366A1 AU 2002350366 A1 AU2002350366 A1 AU 2002350366A1 AU 2002350366 A AU2002350366 A AU 2002350366A AU 2002350366 A AU2002350366 A AU 2002350366A AU 2002350366 A1 AU2002350366 A1 AU 2002350366A1

Authority

AU

Australia

Prior art keywords

phenyl

rac

oxo

ethyl

pyrrolidin

Prior art date

2001-12-31

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• Discuss

• XYVMBSCIEDOIJQ-UHFFFAOYSA-N Squamolone Chemical class NC(=O)N1CCCC1=O XYVMBSCIEDOIJQ-UHFFFAOYSA-N 0.000 title claims description 7
• -1 Hydroxyphenylethyl Chemical group 0.000 claims description 292
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 168
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 36
• OXEUETBFKVCRNP-UHFFFAOYSA-N 9-ethyl-3-carbazolamine Chemical compound NC1=CC=C2N(CC)C3=CC=CC=C3C2=C1 OXEUETBFKVCRNP-UHFFFAOYSA-N 0.000 claims description 26
• 125000000217 alkyl group Chemical group 0.000 claims description 22
• 125000003545 alkoxy group Chemical group 0.000 claims description 14
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 125000002252 acyl group Chemical group 0.000 claims description 9
• 150000002148 esters Chemical class 0.000 claims description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 125000003118 aryl group Chemical group 0.000 claims description 8
• 125000001072 heteroaryl group Chemical group 0.000 claims description 7
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 claims description 6
• 206010003246 arthritis Diseases 0.000 claims description 5
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 206010012601 diabetes mellitus Diseases 0.000 claims description 5
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
• 125000001624 naphthyl group Chemical group 0.000 claims description 5
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 4
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
• 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• 125000005605 benzo group Chemical group 0.000 claims description 4
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• DQNMHCKSNMSIOW-UHFFFAOYSA-N n-(2-methylpropyl)-4-nitro-n-phenylaniline Chemical compound C=1C=C([N+]([O-])=O)C=CC=1N(CC(C)C)C1=CC=CC=C1 DQNMHCKSNMSIOW-UHFFFAOYSA-N 0.000 claims description 4
• BAOWTGGIRWXZEQ-UHFFFAOYSA-N n-(cyclopropylmethyl)-4-nitro-n-phenylaniline Chemical compound C1=CC([N+](=O)[O-])=CC=C1N(C=1C=CC=CC=1)CC1CC1 BAOWTGGIRWXZEQ-UHFFFAOYSA-N 0.000 claims description 4
• ZMUHSCWLMMWGDR-UHFFFAOYSA-N n-benzyl-4-nitro-n-phenylaniline Chemical compound C1=CC([N+](=O)[O-])=CC=C1N(C=1C=CC=CC=1)CC1=CC=CC=C1 ZMUHSCWLMMWGDR-UHFFFAOYSA-N 0.000 claims description 4
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 3
• 125000004104 aryloxy group Chemical group 0.000 claims description 3
• 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
• 229910052736 halogen Inorganic materials 0.000 claims description 3
• 150000002367 halogens Chemical class 0.000 claims description 3
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 3
• 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 3
• 239000012453 solvate Substances 0.000 claims description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
• HVCMPZYQDQNWBN-UHFFFAOYSA-N 4-n-(4,6-dimethylpyrimidin-2-yl)-4-n-ethylbenzene-1,4-diamine Chemical compound N=1C(C)=CC(C)=NC=1N(CC)C1=CC=C(N)C=C1 HVCMPZYQDQNWBN-UHFFFAOYSA-N 0.000 claims 2
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 2
• 229940079593 drug Drugs 0.000 claims 2
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 2
• VCHXKKLOBQMXKH-UHFFFAOYSA-N 4-n-(2-methylpropyl)-4-n-phenylbenzene-1,4-diamine Chemical compound C=1C=C(N)C=CC=1N(CC(C)C)C1=CC=CC=C1 VCHXKKLOBQMXKH-UHFFFAOYSA-N 0.000 claims 1
• AYLAFPRFEFNRSP-UHFFFAOYSA-N 4-n-(4,6-dimethylpyrimidin-2-yl)-4-n-methylbenzene-1,4-diamine Chemical compound N=1C(C)=CC(C)=NC=1N(C)C1=CC=C(N)C=C1 AYLAFPRFEFNRSP-UHFFFAOYSA-N 0.000 claims 1
• SFVBOQCTJBQABR-UHFFFAOYSA-N 4-n-(4,6-dimethylpyrimidin-2-yl)benzene-1,4-diamine Chemical compound CC1=CC(C)=NC(NC=2C=CC(N)=CC=2)=N1 SFVBOQCTJBQABR-UHFFFAOYSA-N 0.000 claims 1
• AFGQTCSHRZSIHO-UHFFFAOYSA-N 4-n-(cyclopropylmethyl)-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1N(C=1C=CC=CC=1)CC1CC1 AFGQTCSHRZSIHO-UHFFFAOYSA-N 0.000 claims 1
• HIWOQWICOFGBEQ-UHFFFAOYSA-N 4-n-ethyl-4-n-phenylbenzene-1,4-diamine Chemical compound C=1C=C(N)C=CC=1N(CC)C1=CC=CC=C1 HIWOQWICOFGBEQ-UHFFFAOYSA-N 0.000 claims 1
• OVSABEXSZWEKHQ-UHFFFAOYSA-N 4-n-methyl-4-n-phenylbenzene-1,4-diamine Chemical compound C=1C=C(N)C=CC=1N(C)C1=CC=CC=C1 OVSABEXSZWEKHQ-UHFFFAOYSA-N 0.000 claims 1
• VRKQEIXDEZVPSY-UHFFFAOYSA-N 4-n-phenyl-4-n-propan-2-ylbenzene-1,4-diamine Chemical compound C=1C=C(N)C=CC=1N(C(C)C)C1=CC=CC=C1 VRKQEIXDEZVPSY-UHFFFAOYSA-N 0.000 claims 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
• FZNCGRZWXLXZSZ-CIQUZCHMSA-N Voglibose Chemical compound OCC(CO)N[C@H]1C[C@](O)(CO)[C@@H](O)[C@H](O)[C@H]1O FZNCGRZWXLXZSZ-CIQUZCHMSA-N 0.000 claims 1
• 229910052799 carbon Inorganic materials 0.000 claims 1
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
• 150000001875 compounds Chemical class 0.000 description 69
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 47
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 46
• 150000001412 amines Chemical class 0.000 description 44
• 102100031765 3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase Human genes 0.000 description 43
• 101000866618 Homo sapiens 3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase Proteins 0.000 description 43
• 239000000047 product Substances 0.000 description 36
• BJSCOTHGFJMOOE-UHFFFAOYSA-N 5-oxopyrrolidine-3-carboxamide Chemical compound NC(=O)C1CNC(=O)C1 BJSCOTHGFJMOOE-UHFFFAOYSA-N 0.000 description 24
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 22
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 18
• IQHXABCGSFAKPN-UHFFFAOYSA-N pyrrolidine-3-carboxamide Chemical compound NC(=O)C1CCNC1 IQHXABCGSFAKPN-UHFFFAOYSA-N 0.000 description 15
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 14
• 150000003839 salts Chemical class 0.000 description 14
• 239000000203 mixture Substances 0.000 description 12
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 10
• 238000000034 method Methods 0.000 description 10
• CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 9
• 229940044174 4-phenylenediamine Drugs 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• 239000002253 acid Substances 0.000 description 8
• GBDDQLTTZULAOS-UHFFFAOYSA-N ethyl 2-(n-(4-aminophenyl)anilino)acetate Chemical compound C=1C=C(N)C=CC=1N(CC(=O)OCC)C1=CC=CC=C1 GBDDQLTTZULAOS-UHFFFAOYSA-N 0.000 description 8
• PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 8
• 229910052739 hydrogen Inorganic materials 0.000 description 8
• 239000001257 hydrogen Substances 0.000 description 8
• 239000000243 solution Substances 0.000 description 8
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
• 101710151321 Melanostatin Proteins 0.000 description 7
• KBADXKUASLYBTH-UHFFFAOYSA-N NC1=CC=C(C=C1)N(C1=CC=CC=C1)C(C(=O)OCC)CCC Chemical compound NC1=CC=C(C=C1)N(C1=CC=CC=C1)C(C(=O)OCC)CCC KBADXKUASLYBTH-UHFFFAOYSA-N 0.000 description 7
• 102100028427 Pro-neuropeptide Y Human genes 0.000 description 7
• 150000001408 amides Chemical class 0.000 description 7
• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 7
• ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 6
• 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 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
• BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 6
• 208000008589 Obesity Diseases 0.000 description 6
• DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 6
• 239000000706 filtrate Substances 0.000 description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
• 235000020824 obesity Nutrition 0.000 description 6
• 150000003254 radicals Chemical class 0.000 description 6
• 125000001424 substituent group Chemical group 0.000 description 6
• HCLQQCCBZYLALX-UHFFFAOYSA-N 1-(5-methoxy-2-methylphenyl)-5-oxopyrrolidine-3-carboxamide Chemical compound COC1=CC=C(C)C(N2C(CC(C2)C(N)=O)=O)=C1 HCLQQCCBZYLALX-UHFFFAOYSA-N 0.000 description 5
• CFRFHWQYWJMEJN-UHFFFAOYSA-N 9h-fluoren-2-amine Chemical compound C1=CC=C2C3=CC=C(N)C=C3CC2=C1 CFRFHWQYWJMEJN-UHFFFAOYSA-N 0.000 description 5
• 125000004432 carbon atom Chemical group C* 0.000 description 5
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
• URPYMXQQVHTUDU-OFGSCBOVSA-N nucleopeptide y Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 URPYMXQQVHTUDU-OFGSCBOVSA-N 0.000 description 5
• 229940079889 pyrrolidonecarboxylic acid Drugs 0.000 description 5
• 239000011541 reaction mixture Substances 0.000 description 5
• 239000002904 solvent Substances 0.000 description 5
• WJEOQDLASMFFOU-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-2-yl)-5-oxopyrrolidine-3-carboxamide Chemical compound O=C1CC(C(=O)N)CN1C1CC2=CC=CC=C2C1 WJEOQDLASMFFOU-UHFFFAOYSA-N 0.000 description 4
• HBNDKVDVGATCAW-UHFFFAOYSA-N 1-(2,5-dimethylphenyl)-5-oxopyrrolidine-3-carboxamide Chemical compound CC1=CC=C(C)C(N2C(CC(C2)C(N)=O)=O)=C1 HBNDKVDVGATCAW-UHFFFAOYSA-N 0.000 description 4
• MUNOBADFTHUUFG-UHFFFAOYSA-N 3-phenylaniline Chemical group NC1=CC=CC(C=2C=CC=CC=2)=C1 MUNOBADFTHUUFG-UHFFFAOYSA-N 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• 230000027455 binding Effects 0.000 description 4
• 150000003857 carboxamides Chemical class 0.000 description 4
• 235000005686 eating Nutrition 0.000 description 4
• LXNZXQYFYFEBPK-UHFFFAOYSA-N ethyl 2-(n-(4-nitrophenyl)anilino)acetate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1N(CC(=O)OCC)C1=CC=CC=C1 LXNZXQYFYFEBPK-UHFFFAOYSA-N 0.000 description 4
• DAYAJPHIZWNGSX-UHFFFAOYSA-N n-(9-ethylcarbazol-3-yl)-1-(2-hydroxy-2-phenylethyl)-5-oxopyrrolidine-3-carboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC(=O)C(CC1=O)CN1CC(O)C1=CC=CC=C1 DAYAJPHIZWNGSX-UHFFFAOYSA-N 0.000 description 4
• ZUOGOMATEORWQP-UHFFFAOYSA-N n-(9-ethylcarbazol-3-yl)-5-oxo-1-(2-propan-2-ylphenyl)pyrrolidine-3-carboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC(=O)C(CC1=O)CN1C1=CC=CC=C1C(C)C ZUOGOMATEORWQP-UHFFFAOYSA-N 0.000 description 4
• QWRHEVZABGJAHU-UHFFFAOYSA-N n-[4-(n-methylanilino)phenyl]-5-oxo-1-(2-propan-2-ylphenyl)pyrrolidine-3-carboxamide Chemical compound CC(C)C1=CC=CC=C1N1C(=O)CC(C(=O)NC=2C=CC(=CC=2)N(C)C=2C=CC=CC=2)C1 QWRHEVZABGJAHU-UHFFFAOYSA-N 0.000 description 4
• 230000000144 pharmacologic effect Effects 0.000 description 4
• 102000005962 receptors Human genes 0.000 description 4
• 108020003175 receptors Proteins 0.000 description 4
• 239000003826 tablet Substances 0.000 description 4
• 238000012360 testing method Methods 0.000 description 4
• OPWKXHIUQKXOSE-UHFFFAOYSA-N 1-(2,5-dimethylphenyl)-5-oxo-n-(4-phenylphenyl)pyrrolidine-3-carboxamide Chemical compound CC1=CC=C(C)C(N2C(CC(C2)C(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)=O)=C1 OPWKXHIUQKXOSE-UHFFFAOYSA-N 0.000 description 3
• PWWLVURNNBTQNS-UHFFFAOYSA-N 1-(2,5-dimethylphenyl)-n-[4-(n-methylanilino)phenyl]-5-oxopyrrolidine-3-carboxamide Chemical compound C=1C=C(NC(=O)C2CC(=O)N(C2)C=2C(=CC=C(C)C=2)C)C=CC=1N(C)C1=CC=CC=C1 PWWLVURNNBTQNS-UHFFFAOYSA-N 0.000 description 3
• MIRPNVFOUKDBEF-UHFFFAOYSA-N 1-(3-fluorophenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound O=C1CC(C(=O)O)CN1C1=CC=CC(F)=C1 MIRPNVFOUKDBEF-UHFFFAOYSA-N 0.000 description 3
• MNAMYXIXVXGCKK-UHFFFAOYSA-N 1-(4-methylphenyl)-5-oxopyrrolidine-3-carboxamide Chemical compound C1=CC(C)=CC=C1N1C(=O)CC(C(N)=O)C1 MNAMYXIXVXGCKK-UHFFFAOYSA-N 0.000 description 3
• OZEOYYGUXATGJM-UHFFFAOYSA-N 1-benzyl-n-(9-ethylcarbazol-3-yl)-5-oxopyrrolidine-3-carboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC(=O)C(CC1=O)CN1CC1=CC=CC=C1 OZEOYYGUXATGJM-UHFFFAOYSA-N 0.000 description 3
• SJODITPGMMSNRF-UHFFFAOYSA-N 2-aminofluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C2=C1 SJODITPGMMSNRF-UHFFFAOYSA-N 0.000 description 3
• 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
• RZNHSEZOLFEFGB-UHFFFAOYSA-N 2-methoxybenzoyl chloride Chemical compound COC1=CC=CC=C1C(Cl)=O RZNHSEZOLFEFGB-UHFFFAOYSA-N 0.000 description 3
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 3
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