CA2092112A1 - Indole and indazole derivatives, for the treatment and prophylaxis of cerebral disorders, their preparation and their use - Google Patents
Indole and indazole derivatives, for the treatment and prophylaxis of cerebral disorders, their preparation and their useInfo
- 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
- 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
- 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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- 125000004043 oxo group Chemical group O=* 0.000 description 1
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- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
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- HRVXPXCISZSDCC-UHFFFAOYSA-N piperidine-4-carbaldehyde Chemical compound O=CC1CCNCC1 HRVXPXCISZSDCC-UHFFFAOYSA-N 0.000 description 1
- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 description 1
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- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
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- 125000003226 pyrazolyl group Chemical group 0.000 description 1
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- 238000006722 reduction reaction Methods 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 229910001958 silver carbonate Inorganic materials 0.000 description 1
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
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- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
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- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 description 1
- 229960001685 tacrine Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
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- 235000002906 tartaric acid Nutrition 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4-65323 | 1992-03-23 | ||
| JP6532392 | 1992-03-23 | ||
| JP915693 | 1993-01-22 | ||
| JP5-9156 | 1993-01-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2092112A1 true CA2092112A1 (en) | 1993-09-24 |
Family
ID=26343823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002092112A Abandoned CA2092112A1 (en) | 1992-03-23 | 1993-03-22 | Indole and indazole derivatives, for the treatment and prophylaxis of cerebral disorders, their preparation and their use |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0562832A1 (enExample) |
| KR (1) | KR930019661A (enExample) |
| CN (1) | CN1081676A (enExample) |
| AU (1) | AU3537893A (enExample) |
| CA (1) | CA2092112A1 (enExample) |
| CZ (1) | CZ47393A3 (enExample) |
| FI (1) | FI931291L (enExample) |
| HU (1) | HU9300828D0 (enExample) |
| IL (1) | IL105139A0 (enExample) |
| NO (1) | NO931040L (enExample) |
| TW (1) | TW226019B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5741801A (en) * | 1993-05-22 | 1998-04-21 | Smithkline Beecham Plc | 5-HT4 receptor antagonist |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW263504B (enExample) * | 1991-10-03 | 1995-11-21 | Pfizer | |
| IT1271352B (it) * | 1993-04-08 | 1997-05-27 | Boehringer Ingelheim Italia | Derivati dell'indolo utili nel trattamento dei disturbi del sistema nervoso centrale |
| US5620973A (en) * | 1993-11-30 | 1997-04-15 | Takeda Chemical Industries, Ltd. | Tetracyclic condensed heterocyclic compounds and their use |
| ES2098186B1 (es) * | 1995-02-09 | 1998-02-01 | Consejo Superior Investigacion | Composiciones farmaceuticas a base de aminometilindoles para su aplicacion terapeutica como neuroprotectores en las enfermedades de parkinson y alzheimer. |
| DE19512639A1 (de) * | 1995-04-05 | 1996-10-10 | Merck Patent Gmbh | Benzonitrile und -fluoride |
| GB2308362A (en) * | 1995-12-19 | 1997-06-25 | Lilly Industries Ltd | Pharmaceutical indole derivatives |
| WO1998046590A1 (en) * | 1997-04-17 | 1998-10-22 | Takeda Chemical Industries, Ltd. | Thermogenic composition and benzazepine thermogenics |
| NZ510685A (en) | 1998-09-30 | 2003-10-31 | Takeda Chemical Industries Ltd | Drugs for improving vesical excretory strength |
| CN1317276C (zh) * | 2000-09-29 | 2007-05-23 | 中国科学院上海药物研究所 | 一类吲哚基哌啶类化合物及其制备方法和用途 |
| CN1589153A (zh) | 2001-12-28 | 2005-03-02 | 武田药品工业株式会社 | 排尿紊乱的预防或治疗 |
| TW200621237A (en) | 2004-11-01 | 2006-07-01 | Wyeth Corp | [(1-h-indazol-3-yl)methyl]phenols and (hydroxyphenyl)(1h-indazol-3-yl)methanones |
| WO2006056873A2 (en) | 2004-11-29 | 2006-06-01 | Warner-Lambert Company Llc | Therapeutic pyrazolo[3,4-b] pyridines and indazoles |
| BRPI0706523A2 (pt) | 2006-01-13 | 2011-01-04 | Wyeth Corp | composto de fórmula i; composição farmacêutica; método de tratamento de distúrbios que estão relacionados com ou são afetados pela inibição da recaptação de norepinefrina, o receptor de 5-ht6 ou o receptor de 5-ht2a; método de tratamento de um distúrbio de aprendizado, de um distúrbio cognitivo, de um distúrbio de memória, de um distúrbio de personalidade, de um distúrbio comportamental, de um distúrbio de movimento, de um distúrbio neurodegenerativo, de abstinência de droga, de distúrbio de sono, de um distúrbio alimentar, de uma toxicidade de droga aguda, de um distúrbio cardiovascular, de uma disfunção sexual, de um distúrbio gastrintestinal, de um distúrbio genitourinário, de um distúrbio de dor, de um distúrbio nervoso ou de um distúrbio de sintoma vasomotor; método de tratamento de doença de alzheimer, de um distúrbio de deficiência da atenção, de esquizofrenia, de doença de parkinson, de discinésia tardia, de ataxia, de bradicinésia, de discinésias paroxìsmicas, de sìndrome da perna irrequieta, de tremor, de tremor essencial, de epilepsia, de apoplexia ou de trauma na cabeça; método de tratamento de doença arterial coronariana, de enfarte do miocárdio, de ataque isquêmico transitório, de angina, de fibrilação atrial, de agregação plaquetária, de risco de formação de coágulo sanguìneo, de sìndrome do intestino irritável, de constipação crÈnica, de doença do refluxo gastrintestinal, de dispepsia, de incontinência urinária por estresse ou de incontinência urinária de urgência; método de tratamento de depressão, de distúrbio compulsivo obsessivo, de tendência ao suicìdio, de distúrbio de ansiedade, de distúrbio bipolar, de distúrbio de pánico, de abstinência de nicotina, de abstinência de álcool, de abstinência de cocaìna, de abstinência de heroìna, de abstinência de anfetamina, de abstinência de drogas narcóticas, de insÈnia, de apnéia do sono, de narcolepsia, de distúrbio afetivo sanzonal, de sìndrome da perna irrequieta, de distúrbio de sono de turno de trabalho, de sìndrome da fase do sono retardada, de anorexia nervosa, de bulimia nervosa, de sìndrome do comer noturno, de superalimentação compulsiva, de sìndrome da fadiga crÈnica, de fibromialgia, de neuropatia de dor, de dor antinociceptiva, de sìndrome da dor crÈnica, de neuropatia diabética, de fogacho ou de suor noturno; e uso de um composto |
| CN102844313B (zh) | 2010-01-28 | 2016-10-05 | 哈佛大学校长及研究员协会 | 提高蛋白酶体活性的组合物和方法 |
| CA2799154A1 (en) | 2010-05-12 | 2011-11-17 | Abbvie Inc. | Indazole inhibitors of kinase |
| US9556166B2 (en) | 2011-05-12 | 2017-01-31 | Proteostasis Therapeutics, Inc. | Proteostasis regulators |
| WO2014116228A1 (en) | 2013-01-25 | 2014-07-31 | President And Fellows Of Harvard College | Usp14 inhibitors for treating or preventing viral infections |
| WO2015073528A1 (en) | 2013-11-12 | 2015-05-21 | Proteostasis Therapeutics, Inc. | Proteasome activity enhancing compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2334358A1 (fr) * | 1975-12-12 | 1977-07-08 | Sogeras | Nouveaux medicaments derives de l'indole |
| FR2477544A1 (fr) * | 1980-03-07 | 1981-09-11 | Pharmindustrie | Nouveaux derives de la chloro-3 quinoleine, procedes pour leur preparation, et leur utilisation comme medicaments |
-
1993
- 1993-03-22 CA CA002092112A patent/CA2092112A1/en not_active Abandoned
- 1993-03-22 TW TW082102226A patent/TW226019B/zh active
- 1993-03-23 KR KR1019930004542A patent/KR930019661A/ko not_active Withdrawn
- 1993-03-23 IL IL105139A patent/IL105139A0/xx unknown
- 1993-03-23 CZ CZ93473A patent/CZ47393A3/cs unknown
- 1993-03-23 AU AU35378/93A patent/AU3537893A/en not_active Abandoned
- 1993-03-23 HU HU9300828A patent/HU9300828D0/hu unknown
- 1993-03-23 NO NO93931040A patent/NO931040L/no unknown
- 1993-03-23 FI FI931291A patent/FI931291L/fi not_active Application Discontinuation
- 1993-03-23 EP EP93302220A patent/EP0562832A1/en not_active Withdrawn
- 1993-03-23 CN CN93105229A patent/CN1081676A/zh active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5741801A (en) * | 1993-05-22 | 1998-04-21 | Smithkline Beecham Plc | 5-HT4 receptor antagonist |
Also Published As
| Publication number | Publication date |
|---|---|
| FI931291A7 (fi) | 1993-09-24 |
| IL105139A0 (en) | 1993-07-08 |
| NO931040L (no) | 1993-09-24 |
| CN1081676A (zh) | 1994-02-09 |
| EP0562832A1 (en) | 1993-09-29 |
| NO931040D0 (no) | 1993-03-23 |
| CZ47393A3 (en) | 1993-11-17 |
| HU9300828D0 (en) | 1993-06-28 |
| AU3537893A (en) | 1993-09-30 |
| TW226019B (enExample) | 1994-07-01 |
| FI931291A0 (fi) | 1993-03-23 |
| KR930019661A (ko) | 1993-10-18 |
| FI931291L (fi) | 1993-09-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |