CA2092112A1 - Indole and indazole derivatives, for the treatment and prophylaxis of cerebral disorders, their preparation and their use - Google Patents

Info

Publication number

CA2092112A1

CA2092112A1 CA002092112A CA2092112A CA2092112A1 CA 2092112 A1 CA2092112 A1 CA 2092112A1 CA 002092112 A CA002092112 A CA 002092112A CA 2092112 A CA2092112 A CA 2092112A CA 2092112 A1 CA2092112 A1 CA 2092112A1

Authority

CA

Canada

Prior art keywords

group

carbon atoms

methyl

piperidyl

groups

Prior art date

1992-03-23

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
• CIPO
• Discuss

• 238000011282 treatment Methods 0.000 title claims abstract description 12
• 238000011321 prophylaxis Methods 0.000 title claims abstract description 9
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title claims description 191
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title claims description 103
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title claims description 103
• 238000002360 preparation method Methods 0.000 title description 20
• 208000018152 Cerebral disease Diseases 0.000 title description 4
• 125000003453 indazolyl group Chemical class N1N=C(C2=C1C=CC=C2)* 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 506
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 57
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 25
• -1 cyanoamino group Chemical group 0.000 claims description 597
• 125000004432 carbon atom Chemical group C* 0.000 claims description 401
• 125000001424 substituent group Chemical group 0.000 claims description 283
• 238000000034 method Methods 0.000 claims description 188
• 125000000217 alkyl group Chemical group 0.000 claims description 167
• 125000003118 aryl group Chemical group 0.000 claims description 148
• 239000000203 mixture Substances 0.000 claims description 145
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 93
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 86
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 81
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 80
• 125000004429 atom Chemical group 0.000 claims description 77
• 125000000623 heterocyclic group Chemical group 0.000 claims description 65
• 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 60
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 59
• 125000002252 acyl group Chemical group 0.000 claims description 58
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 53
• 150000003839 salts Chemical class 0.000 claims description 50
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 46
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 45
• 125000003545 alkoxy group Chemical group 0.000 claims description 42
• 125000006413 ring segment Chemical group 0.000 claims description 40
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 38
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 36
• 125000005843 halogen group Chemical group 0.000 claims description 36
• 229910052757 nitrogen Inorganic materials 0.000 claims description 36
• 239000000460 chlorine Substances 0.000 claims description 33
• ZGPJQMXSYNXKGY-UHFFFAOYSA-N 3-(1-benzylpiperidin-4-yl)-1-(1-methylindol-3-yl)prop-2-en-1-one Chemical compound C12=CC=CC=C2N(C)C=C1C(=O)C=CC(CC1)CCN1CC1=CC=CC=C1 ZGPJQMXSYNXKGY-UHFFFAOYSA-N 0.000 claims description 32
• 229910052801 chlorine Inorganic materials 0.000 claims description 32
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 31
• 239000011737 fluorine Substances 0.000 claims description 31
• 229910052731 fluorine Inorganic materials 0.000 claims description 31
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 29
• 125000005842 heteroatom Chemical group 0.000 claims description 28
• 125000001188 haloalkyl group Chemical group 0.000 claims description 26
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 26
• POOAAJLQXPMBBY-UHFFFAOYSA-N 3-(1-benzylpiperidin-4-yl)-1-(1-methylindol-3-yl)propan-1-one Chemical compound C12=CC=CC=C2N(C)C=C1C(=O)CCC(CC1)CCN1CC1=CC=CC=C1 POOAAJLQXPMBBY-UHFFFAOYSA-N 0.000 claims description 25
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 25
• 229910052760 oxygen Inorganic materials 0.000 claims description 25
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 24
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 23
• 239000001301 oxygen Substances 0.000 claims description 23
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 21
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 19
• 229910052717 sulfur Inorganic materials 0.000 claims description 19
• 125000003277 amino group Chemical group 0.000 claims description 18
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 16
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 16
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
• 239000011593 sulfur Substances 0.000 claims description 15
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 14
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
• 229920006395 saturated elastomer Polymers 0.000 claims description 14
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 13
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 13
• 229910052794 bromium Inorganic materials 0.000 claims description 13
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 12
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 12
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 11
• 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 10
• 125000003282 alkyl amino group Chemical group 0.000 claims description 10
• 125000000304 alkynyl group Chemical group 0.000 claims description 10
• 125000001769 aryl amino group Chemical group 0.000 claims description 10
• RJTZUHVCZIGJMB-UHFFFAOYSA-N hydron;1h-indole;chloride Chemical compound Cl.C1=CC=C2NC=CC2=C1 RJTZUHVCZIGJMB-UHFFFAOYSA-N 0.000 claims description 10
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 9
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 9
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• 229910052702 rhenium Inorganic materials 0.000 claims description 8
• 125000004434 sulfur atom Chemical group 0.000 claims description 8
• 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 7
• 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 7
• 239000000544 cholinesterase inhibitor Substances 0.000 claims description 7
• 230000006735 deficit Effects 0.000 claims description 7
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
• 229910021481 rutherfordium Inorganic materials 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 7
• 229940100578 Acetylcholinesterase inhibitor Drugs 0.000 claims description 6
• 230000002490 cerebral effect Effects 0.000 claims description 6
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
• KVFCFRJUTUCCIF-UHFFFAOYSA-N 1-(5-fluoro-1-methylindol-3-yl)-3-[1-[(3-fluorophenyl)methyl]piperidin-4-yl]prop-2-en-1-one Chemical compound C12=CC(F)=CC=C2N(C)C=C1C(=O)C=CC(CC1)CCN1CC1=CC=CC(F)=C1 KVFCFRJUTUCCIF-UHFFFAOYSA-N 0.000 claims description 5
• KYERMMVGZVZDSP-UHFFFAOYSA-N 1-(5-fluoro-1-methylindol-3-yl)-3-[1-[(3-fluorophenyl)methyl]piperidin-4-yl]propan-1-one Chemical compound C12=CC(F)=CC=C2N(C)C=C1C(=O)CCC(CC1)CCN1CC1=CC=CC(F)=C1 KYERMMVGZVZDSP-UHFFFAOYSA-N 0.000 claims description 5
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• LMNCNGJLZZEFHF-UHFFFAOYSA-N 3-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-1-(1-methylindazol-3-yl)propan-1-one Chemical compound C12=CC=CC=C2N(C)N=C1C(=O)CCC(CC1)CCN1CC1=CC=CC=C1Cl LMNCNGJLZZEFHF-UHFFFAOYSA-N 0.000 claims description 5
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 5
• 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 5
• 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 5
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
• 239000000651 prodrug Substances 0.000 claims description 5
• 229940002612 prodrug Drugs 0.000 claims description 5
• 125000006239 protecting group Chemical group 0.000 claims description 5
• WYHKZCNPAUPZOM-UHFFFAOYSA-N 1-(5-fluoro-1-methylindol-3-yl)-3-[1-[(3-fluorophenyl)methyl]piperidin-4-yl]propan-1-one;trifluoromethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)F.C12=CC(F)=CC=C2N(C)C=C1C(=O)CCC(CC1)CCN1CC1=CC=CC(F)=C1 WYHKZCNPAUPZOM-UHFFFAOYSA-N 0.000 claims description 4
• CFIDEPAWAUVBKK-UHFFFAOYSA-N 3-(1-benzylpiperidin-4-yl)-1-(1-methylindazol-3-yl)propan-1-one Chemical compound C12=CC=CC=C2N(C)N=C1C(=O)CCC(CC1)CCN1CC1=CC=CC=C1 CFIDEPAWAUVBKK-UHFFFAOYSA-N 0.000 claims description 4
• IVKPMPIJWNPYNK-UHFFFAOYSA-N 3-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-1-(1-methylindazol-3-yl)propan-1-one;hydrochloride Chemical compound Cl.C12=CC=CC=C2N(C)N=C1C(=O)CCC(CC1)CCN1CC1=CC=CC=C1Cl IVKPMPIJWNPYNK-UHFFFAOYSA-N 0.000 claims description 4
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
• 125000005128 aryl amino alkyl group Chemical group 0.000 claims description 4
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
• 239000003112 inhibitor Substances 0.000 claims description 4
• 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
• 125000005936 piperidyl group Chemical group 0.000 claims description 4
• 125000005493 quinolyl group Chemical group 0.000 claims description 4
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
• HSBOTWWDXPYWGU-UHFFFAOYSA-N 1-(5-chloro-1-methylindol-3-yl)-3-[1-[(3-chlorophenyl)methyl]piperidin-4-yl]prop-2-en-1-one Chemical compound C12=CC(Cl)=CC=C2N(C)C=C1C(=O)C=CC(CC1)CCN1CC1=CC=CC(Cl)=C1 HSBOTWWDXPYWGU-UHFFFAOYSA-N 0.000 claims description 3
• ZJAJIUZTUYNPDI-UHFFFAOYSA-N 1-(5-chloro-1-methylindol-3-yl)-3-[1-[(3-fluorophenyl)methyl]piperidin-4-yl]prop-2-en-1-one Chemical compound C12=CC(Cl)=CC=C2N(C)C=C1C(=O)C=CC(CC1)CCN1CC1=CC=CC(F)=C1 ZJAJIUZTUYNPDI-UHFFFAOYSA-N 0.000 claims description 3
• GEDVTNIPGGSJCW-UHFFFAOYSA-N 1-(5-chloro-1-methylindol-3-yl)-3-[1-[(3-fluorophenyl)methyl]piperidin-4-yl]propan-1-one Chemical compound C12=CC(Cl)=CC=C2N(C)C=C1C(=O)CCC(CC1)CCN1CC1=CC=CC(F)=C1 GEDVTNIPGGSJCW-UHFFFAOYSA-N 0.000 claims description 3
• KOGCHYYGLNHLEM-UHFFFAOYSA-N 3-(1-benzylpiperidin-4-yl)-1-(1-methylindol-3-yl)propan-1-one;hydrochloride Chemical compound Cl.C12=CC=CC=C2N(C)C=C1C(=O)CCC(CC1)CCN1CC1=CC=CC=C1 KOGCHYYGLNHLEM-UHFFFAOYSA-N 0.000 claims description 3
• QQKKAPZUTRBZBV-UHFFFAOYSA-N 3-(1-benzylpiperidin-4-yl)-1-[1-methyl-5-[[methyl(prop-2-ynyl)amino]methyl]indol-3-yl]propan-1-one Chemical compound C12=CC(CN(CC#C)C)=CC=C2N(C)C=C1C(=O)CCC(CC1)CCN1CC1=CC=CC=C1 QQKKAPZUTRBZBV-UHFFFAOYSA-N 0.000 claims description 3
• NXYFPLUJRQMGID-UHFFFAOYSA-N 3-[1-[(3-chlorophenyl)methyl]piperidin-4-yl]-1-(1-methylindol-3-yl)propan-1-one Chemical compound C12=CC=CC=C2N(C)C=C1C(=O)CCC(CC1)CCN1CC1=CC=CC(Cl)=C1 NXYFPLUJRQMGID-UHFFFAOYSA-N 0.000 claims description 3
• YEXHCZPZLHDUPY-UHFFFAOYSA-N 3-[1-[(3-chlorophenyl)methyl]piperidin-4-yl]-1-(1-methylindol-3-yl)propan-1-one;hydrochloride Chemical compound Cl.C12=CC=CC=C2N(C)C=C1C(=O)CCC(CC1)CCN1CC1=CC=CC(Cl)=C1 YEXHCZPZLHDUPY-UHFFFAOYSA-N 0.000 claims description 3
• ARUBIFMOPYOMOM-UHFFFAOYSA-N 3-[1-[(3-fluorophenyl)methyl]piperidin-4-yl]-1-(1-methylindol-3-yl)prop-2-en-1-one Chemical compound C12=CC=CC=C2N(C)C=C1C(=O)C=CC(CC1)CCN1CC1=CC=CC(F)=C1 ARUBIFMOPYOMOM-UHFFFAOYSA-N 0.000 claims description 3
• 241000124008 Mammalia Species 0.000 claims description 3
• MHVXYOLJIIWSGY-UHFFFAOYSA-N [3-(1-benzylpiperidin-4-yl)-1-(1-methylindol-3-yl)propyl] acetate Chemical compound C=1N(C)C2=CC=CC=C2C=1C(OC(=O)C)CCC(CC1)CCN1CC1=CC=CC=C1 MHVXYOLJIIWSGY-UHFFFAOYSA-N 0.000 claims description 3
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
• 125000004122 cyclic group Chemical group 0.000 claims description 3
• 150000002148 esters Chemical class 0.000 claims description 3
• 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 3
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
• 125000004193 piperazinyl group Chemical group 0.000 claims description 3
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• XXWGYARPFQRSHS-UHFFFAOYSA-N 1-(5-chloro-1-methylindol-3-yl)-3-[1-[(3-chlorophenyl)methyl]piperidin-4-yl]propan-1-one;hydrochloride Chemical compound Cl.C12=CC(Cl)=CC=C2N(C)C=C1C(=O)CCC(CC1)CCN1CC1=CC=CC(Cl)=C1 XXWGYARPFQRSHS-UHFFFAOYSA-N 0.000 claims description 2
• BOBNDSJRIUWNRY-UHFFFAOYSA-N 3-(1-benzylpiperidin-4-yl)-1-(1-methylindazol-3-yl)propan-1-one;hydrochloride Chemical compound Cl.C12=CC=CC=C2N(C)N=C1C(=O)CCC(CC1)CCN1CC1=CC=CC=C1 BOBNDSJRIUWNRY-UHFFFAOYSA-N 0.000 claims description 2
• AUHBVENLJYWQDL-UHFFFAOYSA-N 3-(1-benzylpiperidin-4-yl)-1-(1-methylindazol-3-yl)propan-1-one;oxalic acid Chemical compound OC(=O)C(O)=O.C12=CC=CC=C2N(C)N=C1C(=O)CCC(CC1)CCN1CC1=CC=CC=C1 AUHBVENLJYWQDL-UHFFFAOYSA-N 0.000 claims description 2
• WARXIUVMCRZSFB-UHFFFAOYSA-N 3-(1-benzylpiperidin-4-yl)-1-(1-methylindol-3-yl)propan-1-one;oxalic acid Chemical compound OC(=O)C(O)=O.C12=CC=CC=C2N(C)C=C1C(=O)CCC(CC1)CCN1CC1=CC=CC=C1 WARXIUVMCRZSFB-UHFFFAOYSA-N 0.000 claims description 2
• DXTNMBVGMHZPNE-UHFFFAOYSA-N 3-(1-benzylpiperidin-4-yl)-1-(1-methylindol-5-yl)propan-1-one Chemical compound C=1C=C2N(C)C=CC2=CC=1C(=O)CCC(CC1)CCN1CC1=CC=CC=C1 DXTNMBVGMHZPNE-UHFFFAOYSA-N 0.000 claims description 2
• GGVOZPSQXLDGRT-UHFFFAOYSA-N 3-(1-benzylpiperidin-4-yl)-1-(5-chloro-1-methylindol-3-yl)prop-2-en-1-one Chemical compound C12=CC(Cl)=CC=C2N(C)C=C1C(=O)C=CC(CC1)CCN1CC1=CC=CC=C1 GGVOZPSQXLDGRT-UHFFFAOYSA-N 0.000 claims description 2
• HKEYPGYIMBOGQH-UHFFFAOYSA-N 3-(1-benzylpiperidin-4-yl)-1-(5-chloro-1-methylindol-3-yl)propan-1-one Chemical compound C12=CC(Cl)=CC=C2N(C)C=C1C(=O)CCC(CC1)CCN1CC1=CC=CC=C1 HKEYPGYIMBOGQH-UHFFFAOYSA-N 0.000 claims description 2
• SFRXKQZZNCSOSE-UHFFFAOYSA-N 3-(1-benzylpiperidin-4-yl)-1-(5-fluoro-1-methylindol-3-yl)prop-2-en-1-one Chemical compound C12=CC(F)=CC=C2N(C)C=C1C(=O)C=CC(CC1)CCN1CC1=CC=CC=C1 SFRXKQZZNCSOSE-UHFFFAOYSA-N 0.000 claims description 2
• QCXVKFFIZCROJD-UHFFFAOYSA-N 3-(1-benzylpiperidin-4-yl)-1-(5-fluoro-1-methylindol-3-yl)propan-1-one Chemical compound C12=CC(F)=CC=C2N(C)C=C1C(=O)CCC(CC1)CCN1CC1=CC=CC=C1 QCXVKFFIZCROJD-UHFFFAOYSA-N 0.000 claims description 2
• CMCMJCHGRYKZTQ-UHFFFAOYSA-N 3-(1-benzylpiperidin-4-yl)-1-(6-chloro-1-methylindol-3-yl)propan-1-one Chemical compound C12=CC=C(Cl)C=C2N(C)C=C1C(=O)CCC(CC1)CCN1CC1=CC=CC=C1 CMCMJCHGRYKZTQ-UHFFFAOYSA-N 0.000 claims description 2
• DHMNLSZWSJWTGI-UHFFFAOYSA-N 3-[1-[(3-fluorophenyl)methyl]piperidin-4-yl]-1-(1-methylindol-3-yl)propan-1-one Chemical compound C12=CC=CC=C2N(C)C=C1C(=O)CCC(CC1)CCN1CC1=CC=CC(F)=C1 DHMNLSZWSJWTGI-UHFFFAOYSA-N 0.000 claims description 2
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
• 239000005977 Ethylene Substances 0.000 claims description 2
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 2
• 125000002947 alkylene group Chemical group 0.000 claims description 2
• 125000004104 aryloxy group Chemical group 0.000 claims description 2
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
• 125000005322 morpholin-1-yl group Chemical group 0.000 claims description 2
• 239000008194 pharmaceutical composition Substances 0.000 claims description 2
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
• 125000006308 propyl amino group Chemical group 0.000 claims description 2
• 229910052703 rhodium Inorganic materials 0.000 claims description 2
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