RU2077530C1 - Замещенные тетрагидро-, или гексагидроциклопент /в/ индолы, или их фармацевтически приемлемые аддитивные соли и способы их получения - Google Patents
Замещенные тетрагидро-, или гексагидроциклопент /в/ индолы, или их фармацевтически приемлемые аддитивные соли и способы их получения Download PDFInfo
- Publication number
- RU2077530C1 RU2077530C1 SU925010763A SU5010763A RU2077530C1 RU 2077530 C1 RU2077530 C1 RU 2077530C1 SU 925010763 A SU925010763 A SU 925010763A SU 5010763 A SU5010763 A SU 5010763A RU 2077530 C1 RU2077530 C1 RU 2077530C1
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- indol
- lower alkyl
- hydrogen
- tetrahydrocyclopent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 22
- 150000003839 salts Chemical class 0.000 title claims description 5
- 150000002475 indoles Chemical class 0.000 title claims 4
- 239000000654 additive Substances 0.000 title 1
- 230000000996 additive effect Effects 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 98
- 150000001875 compounds Chemical class 0.000 claims abstract description 97
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 53
- 239000001257 hydrogen Substances 0.000 claims abstract description 28
- 230000000694 effects Effects 0.000 claims abstract description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 8
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims abstract description 5
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims abstract description 4
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 3
- 230000009467 reduction Effects 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 108010022752 Acetylcholinesterase Proteins 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 229940022698 acetylcholinesterase Drugs 0.000 claims description 8
- 150000002466 imines Chemical class 0.000 claims description 6
- 239000012279 sodium borohydride Substances 0.000 claims description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 5
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 4
- 230000003993 interaction Effects 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- AQNHAQXMOWRTRZ-UHFFFAOYSA-N 1,2,3,3a,4,4a-hexahydrocyclopenta[b]indole Chemical class N1C2C=CC=CC2=C2C1CCC2 AQNHAQXMOWRTRZ-UHFFFAOYSA-N 0.000 claims 2
- 102000012440 Acetylcholinesterase Human genes 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 39
- 239000003814 drug Substances 0.000 abstract description 13
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 9
- 239000000126 substance Substances 0.000 abstract description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 103
- 239000000203 mixture Substances 0.000 description 90
- 229910052757 nitrogen Inorganic materials 0.000 description 80
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 61
- 238000006243 chemical reaction Methods 0.000 description 51
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- -1 hydroxy, amino Chemical group 0.000 description 46
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- 238000000921 elemental analysis Methods 0.000 description 40
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 28
- 239000011734 sodium Substances 0.000 description 28
- 239000007787 solid Substances 0.000 description 28
- 239000003921 oil Substances 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000010410 layer Substances 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 125000003118 aryl group Chemical group 0.000 description 20
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 19
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 19
- 235000019439 ethyl acetate Nutrition 0.000 description 18
- 239000002904 solvent Substances 0.000 description 17
- 239000000758 substrate Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 17
- 238000004809 thin layer chromatography Methods 0.000 description 17
- 102000010909 Monoamine Oxidase Human genes 0.000 description 16
- 108010062431 Monoamine oxidase Proteins 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 150000001412 amines Chemical class 0.000 description 16
- 238000003818 flash chromatography Methods 0.000 description 16
- 238000004458 analytical method Methods 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 13
- 239000000741 silica gel Substances 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- 239000000872 buffer Substances 0.000 description 12
- 229940079593 drug Drugs 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 238000001914 filtration Methods 0.000 description 11
- 239000008363 phosphate buffer Substances 0.000 description 11
- 210000001519 tissue Anatomy 0.000 description 11
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 229960002896 clonidine Drugs 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 210000004556 brain Anatomy 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 102100033639 Acetylcholinesterase Human genes 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 8
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 8
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 8
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 8
- KIUMMUBSPKGMOY-UHFFFAOYSA-N 3,3'-Dithiobis(6-nitrobenzoic acid) Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(SSC=2C=C(C(=CC=2)[N+]([O-])=O)C(O)=O)=C1 KIUMMUBSPKGMOY-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 238000007796 conventional method Methods 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 7
- ZCRSTOXGLODCIE-UHFFFAOYSA-N 1,2,3,4-tetrahydrocyclopenta[b]indol-3-amine Chemical compound N1C2=CC=CC=C2C2=C1C(N)CC2 ZCRSTOXGLODCIE-UHFFFAOYSA-N 0.000 description 6
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 6
- ADFOQBFSUMXJNV-UHFFFAOYSA-N 3-benzylimino-4-methyl-1,2-dihydrocyclopenta[b]indol-7-ol Chemical compound C1CC=2C3=CC(O)=CC=C3N(C)C=2C1=NCC1=CC=CC=C1 ADFOQBFSUMXJNV-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
- 229930006000 Sucrose Natural products 0.000 description 6
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 239000000935 antidepressant agent Substances 0.000 description 6
- 229940005513 antidepressants Drugs 0.000 description 6
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 6
- 230000027455 binding Effects 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 229940088598 enzyme Drugs 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000011550 stock solution Substances 0.000 description 6
- 239000005720 sucrose Substances 0.000 description 6
- FYVOUJQGOXSKBI-UHFFFAOYSA-N (4-methyl-3-oxo-1,2-dihydrocyclopenta[b]indol-7-yl) 2-chloroacetate Chemical compound C12=CC(OC(=O)CCl)=CC=C2N(C)C2=C1CCC2=O FYVOUJQGOXSKBI-UHFFFAOYSA-N 0.000 description 5
- 208000024827 Alzheimer disease Diseases 0.000 description 5
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000004350 aryl cycloalkyl group Chemical group 0.000 description 5
- 238000003556 assay Methods 0.000 description 5
- 230000001713 cholinergic effect Effects 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000001632 sodium acetate Substances 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- ORVPXPKEZLTMNW-UHFFFAOYSA-N 1h-indol-7-ol Chemical compound OC1=CC=CC2=C1NC=C2 ORVPXPKEZLTMNW-UHFFFAOYSA-N 0.000 description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- UOVWNMQWTYQKHT-UHFFFAOYSA-N 3-(cyclopropylamino)-4-methyl-2,3-dihydro-1h-cyclopenta[b]indol-7-ol Chemical compound C1CC=2C3=CC(O)=CC=C3N(C)C=2C1NC1CC1 UOVWNMQWTYQKHT-UHFFFAOYSA-N 0.000 description 4
- KZFRRUKQNOAHAY-UHFFFAOYSA-N 7-hydroxy-4-methyl-1,2-dihydrocyclopenta[b]indol-3-one Chemical compound C12=CC(O)=CC=C2N(C)C2=C1CCC2=O KZFRRUKQNOAHAY-UHFFFAOYSA-N 0.000 description 4
- 102000003914 Cholinesterases Human genes 0.000 description 4
- 108090000322 Cholinesterases Proteins 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- DKJMOJVEFCYLMK-UHFFFAOYSA-N [3-(cyclopropylamino)-4-methyl-2,3-dihydro-1h-cyclopenta[b]indol-7-yl] n-methylcarbamate Chemical compound C1CC=2C3=CC(OC(=O)NC)=CC=C3N(C)C=2C1NC1CC1 DKJMOJVEFCYLMK-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910000085 borane Inorganic materials 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000013058 crude material Substances 0.000 description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 description 4
- 230000007812 deficiency Effects 0.000 description 4
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 150000002923 oximes Chemical class 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 4
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 3
- KDGGIBYZEVGMMS-UHFFFAOYSA-N (4-methyl-3-oxo-1,2-dihydrocyclopenta[b]indol-7-yl) n-methylcarbamate Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)C2=C1CCC2=O KDGGIBYZEVGMMS-UHFFFAOYSA-N 0.000 description 3
- 125000001847 2-phenylcyclopropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1([H])C([H])([H])C1([H])* 0.000 description 3
- DOFOKHVRNHCXPN-UHFFFAOYSA-N 3-(benzylamino)-4-methyl-2,3,3a,8b-tetrahydro-1h-cyclopenta[b]indol-7-ol Chemical compound C1CC2C3=CC(O)=CC=C3N(C)C2C1NCC1=CC=CC=C1 DOFOKHVRNHCXPN-UHFFFAOYSA-N 0.000 description 3
- QYIMCTXMRIGXSV-UHFFFAOYSA-N 3-(cyclopropylamino)-4-methyl-2,3,3a,8b-tetrahydro-1h-cyclopenta[b]indol-7-ol Chemical compound C1CC2C3=CC(O)=CC=C3N(C)C2C1NC1CC1 QYIMCTXMRIGXSV-UHFFFAOYSA-N 0.000 description 3
- XOCFDXPDWJXKEG-UHFFFAOYSA-N 3-amino-4-methyl-2,3,3a,8b-tetrahydro-1h-cyclopenta[b]indol-7-ol Chemical compound C12=CC(O)=CC=C2N(C)C2C1CCC2N XOCFDXPDWJXKEG-UHFFFAOYSA-N 0.000 description 3
- 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 3
- JHRAQVUUGFXPMG-UHFFFAOYSA-N 4-methyl-1,2-dihydrocyclopenta[b]indol-3-one Chemical compound C12=CC=CC=C2N(C)C2=C1CCC2=O JHRAQVUUGFXPMG-UHFFFAOYSA-N 0.000 description 3
- LMLOUSOYXTUHPC-UHFFFAOYSA-N 4-methyl-2,3,3a,8b-tetrahydro-1h-cyclopenta[b]indol-3-amine Chemical compound C12=CC=CC=C2N(C)C2C1CCC2N LMLOUSOYXTUHPC-UHFFFAOYSA-N 0.000 description 3
- RUCUDKHUQRVQKL-UHFFFAOYSA-N 4-methyl-2,3-dihydro-1h-cyclopenta[b]indol-3-amine Chemical compound C12=CC=CC=C2N(C)C2=C1CCC2N RUCUDKHUQRVQKL-UHFFFAOYSA-N 0.000 description 3
- WWYFMHNPXBAFML-UHFFFAOYSA-N 7-(2-chloroacetyl)-4-methyl-1,2-dihydrocyclopenta[b]indol-3-one Chemical compound C12=CC(C(=O)CCl)=CC=C2N(C)C2=C1CCC2=O WWYFMHNPXBAFML-UHFFFAOYSA-N 0.000 description 3
- 229930000680 A04AD01 - Scopolamine Natural products 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 0 CC(*)*(C(CC(C)(*)CC(**)C1)C1C1CC*(C)C2)C1C2C(C)[N+](C(*)*I)[O-] Chemical compound CC(*)*(C(CC(C)(*)CC(**)C1)C1C1CC*(C)C2)C1C2C(C)[N+](C(*)*I)[O-] 0.000 description 3
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 3
- STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 description 3
- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 3
- 229910000990 Ni alloy Inorganic materials 0.000 description 3
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 241000700157 Rattus norvegicus Species 0.000 description 3
- 229940124639 Selective inhibitor Drugs 0.000 description 3
- LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical compound [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 description 3
- 150000001263 acyl chlorides Chemical class 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229940048961 cholinesterase Drugs 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 description 3
- 230000030214 innervation Effects 0.000 description 3
- AGJSNMGHAVDLRQ-HUUJSLGLSA-N methyl (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-HUUJSLGLSA-N 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- 229960002748 norepinephrine Drugs 0.000 description 3
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 3
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 3
- 229960002646 scopolamine Drugs 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- CEPKMXXLBYMZCT-UHFFFAOYSA-N (3-benzylimino-4-methyl-1,2-dihydrocyclopenta[b]indol-7-yl) n-methylcarbamate Chemical compound C1CC=2C3=CC(OC(=O)NC)=CC=C3N(C)C=2C1=NCC1=CC=CC=C1 CEPKMXXLBYMZCT-UHFFFAOYSA-N 0.000 description 2
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- JSWVIEVUCPOOFB-UHFFFAOYSA-N 3-cyclopropylimino-4-methyl-1,2-dihydrocyclopenta[b]indol-7-ol Chemical compound C1CC=2C3=CC(O)=CC=C3N(C)C=2C1=NC1CC1 JSWVIEVUCPOOFB-UHFFFAOYSA-N 0.000 description 2
- ZJOKMMLPDUIFIH-UHFFFAOYSA-N 3-hydroxyimino-4-methyl-1,2-dihydrocyclopenta[b]indol-7-ol Chemical compound C12=CC(O)=CC=C2N(C)C2=C1CCC2=NO ZJOKMMLPDUIFIH-UHFFFAOYSA-N 0.000 description 2
- WMYQAKANKREQLM-UHFFFAOYSA-N 7-chloro-1h-indole Chemical compound ClC1=CC=CC2=C1NC=C2 WMYQAKANKREQLM-UHFFFAOYSA-N 0.000 description 2
- 229940124596 AChE inhibitor Drugs 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 208000026139 Memory disease Diseases 0.000 description 2
- NODAYMBGYRYLKA-UHFFFAOYSA-N N-(2,4-dihydro-1H-cyclopenta[b]indol-3-ylidene)hydroxylamine Chemical compound N1C2=CC=CC=C2C2=C1C(=NO)CC2 NODAYMBGYRYLKA-UHFFFAOYSA-N 0.000 description 2
- 241001274216 Naso Species 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- LLRCMNPFPAPXLK-UHFFFAOYSA-N [4-methyl-3-(methylcarbamoyloxyimino)-1,2-dihydrocyclopenta[b]indol-7-yl] n-methylcarbamate Chemical compound CN1C2=CC=C(OC(=O)NC)C=C2C2=C1C(=NOC(=O)NC)CC2 LLRCMNPFPAPXLK-UHFFFAOYSA-N 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 229960004373 acetylcholine Drugs 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- AQSGVJPWUBASAJ-UHFFFAOYSA-N benzyl n-(7-hydroxy-4-methyl-2,3,3a,8b-tetrahydro-1h-cyclopenta[b]indol-3-yl)carbamate Chemical compound C1CC2C3=CC(O)=CC=C3N(C)C2C1NC(=O)OCC1=CC=CC=C1 AQSGVJPWUBASAJ-UHFFFAOYSA-N 0.000 description 2
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 210000001638 cerebellum Anatomy 0.000 description 2
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 description 2
- OWQNHWQBHFQNCR-UHFFFAOYSA-N cyclopropanamine;1,2,3,4-tetrahydrocyclopenta[b]indole;hydrochloride Chemical compound Cl.NC1CC1.N1C2=CC=CC=C2C2=C1CCC2 OWQNHWQBHFQNCR-UHFFFAOYSA-N 0.000 description 2
- JECGJAUESCVZCF-UHFFFAOYSA-N cyclopropanamine;4-methyl-2,3-dihydro-1h-cyclopenta[b]indole;naphthalene-2-sulfonic acid Chemical compound NC1CC1.C12=CC=CC=C2N(C)C2=C1CCC2.C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 JECGJAUESCVZCF-UHFFFAOYSA-N 0.000 description 2
- 229960003638 dopamine Drugs 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 230000007074 memory dysfunction Effects 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 2
- ASGHNSYRMFQMFU-UHFFFAOYSA-N n-(4-methyl-1,2-dihydrocyclopenta[b]indol-3-ylidene)hydroxylamine Chemical compound C12=CC=CC=C2N(C)C2=C1CCC2=NO ASGHNSYRMFQMFU-UHFFFAOYSA-N 0.000 description 2
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 2
- 210000001577 neostriatum Anatomy 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 230000009871 nonspecific binding Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- 229940076279 serotonin Drugs 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 239000008174 sterile solution Substances 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 description 1
- IGLYMJRIWWIQQE-QUOODJBBSA-N (1S,2R)-2-phenylcyclopropan-1-amine (1R,2S)-2-phenylcyclopropan-1-amine Chemical compound N[C@H]1C[C@@H]1C1=CC=CC=C1.N[C@@H]1C[C@H]1C1=CC=CC=C1 IGLYMJRIWWIQQE-QUOODJBBSA-N 0.000 description 1
- FMCAFXHLMUOIGG-JTJHWIPRSA-N (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-JTJHWIPRSA-N 0.000 description 1
- FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 description 1
- MFYJTVALBSLGNB-UHFFFAOYSA-N (3-acetyloxyimino-4-methyl-1,2-dihydrocyclopenta[b]indol-7-yl) acetate Chemical compound CN1C2=CC=C(OC(C)=O)C=C2C2=C1C(=NOC(=O)C)CC2 MFYJTVALBSLGNB-UHFFFAOYSA-N 0.000 description 1
- VNIBCEAQZMCUGQ-UHFFFAOYSA-N (4-methyl-3-prop-2-ynylimino-1,2-dihydrocyclopenta[b]indol-7-yl) n-methylcarbamate Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)C2=C1CCC2=NCC#C VNIBCEAQZMCUGQ-UHFFFAOYSA-N 0.000 description 1
- QMWWTQMWBNOMGD-UHFFFAOYSA-N 1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-3-amine Chemical compound C1=CC=C2C3CCC(N)C3NC2=C1 QMWWTQMWBNOMGD-UHFFFAOYSA-N 0.000 description 1
- CONLUVOMPNENPM-UHFFFAOYSA-N 1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-3-amine;naphthalene-2-sulfonic acid Chemical compound C1=CC=C2C3CCC(N)C3NC2=C1.C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 CONLUVOMPNENPM-UHFFFAOYSA-N 0.000 description 1
- CVFPOCUUFZKSOU-UHFFFAOYSA-N 1-(1H-indol-7-yloxy)-N-methylmethanamine Chemical compound CNCOC1=C2C(=CC=C1)C=CN2 CVFPOCUUFZKSOU-UHFFFAOYSA-N 0.000 description 1
- YQIQQLVXRIOPIQ-UHFFFAOYSA-N 1-(7-hydroxy-4-methyl-2,3,3a,8b-tetrahydro-1h-cyclopenta[b]indol-3-yl)-3-methylurea;hydrate;hydrochloride Chemical compound O.Cl.C1=C(O)C=C2C3CCC(NC(=O)NC)C3N(C)C2=C1 YQIQQLVXRIOPIQ-UHFFFAOYSA-N 0.000 description 1
- BGXFVOAOCZABIN-UHFFFAOYSA-N 1-amino-7-hydroxy-n,4-dimethyl-2,3,3a,8b-tetrahydro-1h-cyclopenta[b]indole-3-carboxamide;hydrate;hydrochloride Chemical compound O.Cl.C1=C(O)C=C2C3C(N)CC(C(=O)NC)C3N(C)C2=C1 BGXFVOAOCZABIN-UHFFFAOYSA-N 0.000 description 1
- RBGBPPAGBRWDJS-UHFFFAOYSA-N 1-amino-N-benzyl-7-hydroxy-N,4-dimethyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]indole-3-carboxamide Chemical compound CN1C2C(C=3C=C(C=CC1=3)O)C(CC2C(=O)N(C)CC1=CC=CC=C1)N RBGBPPAGBRWDJS-UHFFFAOYSA-N 0.000 description 1
- UJBTURSTQSFTAJ-UHFFFAOYSA-N 1-cyclopropyl-3-(7-hydroxy-4-methyl-2,3,3a,8b-tetrahydro-1h-cyclopenta[b]indol-3-yl)-1-methylurea Chemical compound C1CC(C2=CC(O)=CC=C2N2C)C2C1NC(=O)N(C)C1CC1 UJBTURSTQSFTAJ-UHFFFAOYSA-N 0.000 description 1
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
- DQFTXSFPAYVEQQ-UHFFFAOYSA-N 1-imino-4-methyl-3-(2-morpholin-4-ylethyl)-2,3-dihydrocyclopenta[b]indol-7-ol Chemical compound CN1C2=C(C=3C=C(C=CC1=3)O)C(CC2CCN1CCOCC1)=N DQFTXSFPAYVEQQ-UHFFFAOYSA-N 0.000 description 1
- LTEFVHUXJXVGQD-UHFFFAOYSA-N 1-imino-4-methyl-3-prop-2-ynyl-2,3-dihydrocyclopenta[b]indol-7-ol Chemical compound CN1C2=C(C=3C=C(C=CC1=3)O)C(CC2CC#C)=N LTEFVHUXJXVGQD-UHFFFAOYSA-N 0.000 description 1
- MUCCFMYUBWFNQU-UHFFFAOYSA-N 1h-indol-7-yl n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC2=C1NC=C2 MUCCFMYUBWFNQU-UHFFFAOYSA-N 0.000 description 1
- VFWIQXDDUMNRKG-UHFFFAOYSA-N 2,4-dihydro-1h-cyclopenta[b]indol-3-one Chemical compound N1C2=CC=CC=C2C2=C1C(=O)CC2 VFWIQXDDUMNRKG-UHFFFAOYSA-N 0.000 description 1
- JZWBTXBZJXTKBF-UHFFFAOYSA-N 2-(3-acetyloxyimino-4-methyl-1,2-dihydrocyclopenta[b]indol-7-yl)acetic acid Chemical compound CN1C2=CC=C(CC(O)=O)C=C2C2=C1C(=NOC(=O)C)CC2 JZWBTXBZJXTKBF-UHFFFAOYSA-N 0.000 description 1
- WJAXXWSZNSFVNG-UHFFFAOYSA-N 2-bromoethanamine;hydron;bromide Chemical compound [Br-].[NH3+]CCBr WJAXXWSZNSFVNG-UHFFFAOYSA-N 0.000 description 1
- MAOMSFTUTQGMQO-UHFFFAOYSA-N 3-(benzylamino)-4-methyl-2,3-dihydro-1h-cyclopenta[b]indol-7-ol Chemical compound C1CC=2C3=CC(O)=CC=C3N(C)C=2C1NCC1=CC=CC=C1 MAOMSFTUTQGMQO-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- FNFDOGSZVUKQTC-UHFFFAOYSA-N 4-methyl-2,3,3a,8b-tetrahydro-1h-cyclopenta[b]indol-3-amine;naphthalene-2-sulfonic acid Chemical compound C12=CC=CC=C2N(C)C2C1CCC2N.C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 FNFDOGSZVUKQTC-UHFFFAOYSA-N 0.000 description 1
- NJWXIMGCNIZDFH-UHFFFAOYSA-N 4-methyl-2,3-dihydro-1h-cyclopenta[b]indol-3-amine;hydrochloride Chemical compound Cl.C12=CC=CC=C2N(C)C2=C1CCC2N NJWXIMGCNIZDFH-UHFFFAOYSA-N 0.000 description 1
- GWMCLDUDLHVMIQ-UHFFFAOYSA-N 4-methyl-3-(2-morpholin-4-ylethylimino)-1,2-dihydrocyclopenta[b]indol-7-ol Chemical compound C1CC=2C3=CC(O)=CC=C3N(C)C=2C1=NCCN1CCOCC1 GWMCLDUDLHVMIQ-UHFFFAOYSA-N 0.000 description 1
- VBRUULPETPWKNW-UHFFFAOYSA-N 4-methyl-3-(2-phenylethylamino)-2,3-dihydro-1H-cyclopenta[b]indol-7-ol Chemical compound CN1C2=C(C=3C=C(C=CC1=3)O)CCC2NCCC1=CC=CC=C1 VBRUULPETPWKNW-UHFFFAOYSA-N 0.000 description 1
- ZALFNAGIOGUKQJ-UHFFFAOYSA-N 4-methyl-3-(2-phenylethylimino)-1,2-dihydrocyclopenta[b]indol-7-ol Chemical compound C1CC=2C3=CC(O)=CC=C3N(C)C=2C1=NCCC1=CC=CC=C1 ZALFNAGIOGUKQJ-UHFFFAOYSA-N 0.000 description 1
- SDHCRJJYHBMADB-UHFFFAOYSA-N 4-methyl-3-prop-2-ynylimino-1,2-dihydrocyclopenta[b]indol-7-ol Chemical compound C12=CC(O)=CC=C2N(C)C2=C1CCC2=NCC#C SDHCRJJYHBMADB-UHFFFAOYSA-N 0.000 description 1
- GFNUUAVJKWUJDL-UHFFFAOYSA-N 7-methoxy-2,4-dihydro-1h-cyclopenta[b]indol-3-one Chemical compound C12=CC(OC)=CC=C2NC2=C1CCC2=O GFNUUAVJKWUJDL-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 102100028661 Amine oxidase [flavin-containing] A Human genes 0.000 description 1
- 101710185917 Amine oxidase [flavin-containing] A Proteins 0.000 description 1
- 102100028116 Amine oxidase [flavin-containing] B Human genes 0.000 description 1
- 101710185931 Amine oxidase [flavin-containing] B Proteins 0.000 description 1
- AKIDHRQFGKPXCB-BTJKTKAUSA-N C(\C=C/C(=O)O)(=O)O.NC1CCC=2N(C=3C=CC(=CC3C21)O)C Chemical compound C(\C=C/C(=O)O)(=O)O.NC1CCC=2N(C=3C=CC(=CC3C21)O)C AKIDHRQFGKPXCB-BTJKTKAUSA-N 0.000 description 1
- LWYIWAOBTJPOKZ-UHFFFAOYSA-N C1=C(OC(=O)NC)C=CC2=NC3=CC=C(N)C3=C21 Chemical compound C1=C(OC(=O)NC)C=CC2=NC3=CC=C(N)C3=C21 LWYIWAOBTJPOKZ-UHFFFAOYSA-N 0.000 description 1
- QEHSRKFSGDLKJV-UHFFFAOYSA-N CN1C2=C(C=3C=CC=CC1=3)CCC2=NC1C(C1)C1=CC=CC=C1 Chemical compound CN1C2=C(C=3C=CC=CC1=3)CCC2=NC1C(C1)C1=CC=CC=C1 QEHSRKFSGDLKJV-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 206010048650 Cholinesterase inhibition Diseases 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- NYMGNSNKLVNMIA-UHFFFAOYSA-N Iproniazid Chemical compound CC(C)NNC(=O)C1=CC=NC=C1 NYMGNSNKLVNMIA-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- BLNBLAUKRNGONI-UHFFFAOYSA-N N-(7-methoxy-2,4-dihydro-1H-cyclopenta[b]indol-3-ylidene)hydroxylamine Chemical compound C12=CC(OC)=CC=C2NC2=C1CCC2=NO BLNBLAUKRNGONI-UHFFFAOYSA-N 0.000 description 1
- PUVXZQSZJISFQJ-UHFFFAOYSA-N N-benzyl-4-methyl-1,2-dihydrocyclopenta[b]indol-3-imine Chemical compound CN1C2=C(C=3C=CC=CC1=3)CCC2=NCC1=CC=CC=C1 PUVXZQSZJISFQJ-UHFFFAOYSA-N 0.000 description 1
- LADAPGCKOUERIS-UHFFFAOYSA-N N-cyclopropyl-1,2,3,4-tetrahydrocyclopenta[b]indol-3-amine Chemical compound C1(CC1)NC1CCC2=C1NC=1C=CC=CC21 LADAPGCKOUERIS-UHFFFAOYSA-N 0.000 description 1
- PHXQIAWFIIMOKG-UHFFFAOYSA-N NClO Chemical compound NClO PHXQIAWFIIMOKG-UHFFFAOYSA-N 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 description 1
- QCHFTSOMWOSFHM-UHFFFAOYSA-N SJ000285536 Natural products C1OC(=O)C(CC)C1CC1=CN=CN1C QCHFTSOMWOSFHM-UHFFFAOYSA-N 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- DEAAEYIQTDENFV-UHFFFAOYSA-N [3-(cyclopropylamino)-4-methyl-2,3,3a,8b-tetrahydro-1h-cyclopenta[b]indol-7-yl] n-methylcarbamate Chemical compound C1CC2C3=CC(OC(=O)NC)=CC=C3N(C)C2C1NC1CC1 DEAAEYIQTDENFV-UHFFFAOYSA-N 0.000 description 1
- MNLJJPCEPAYXFB-UHFFFAOYSA-N [4-methyl-3-(2-morpholin-4-ylethylamino)-2,3-dihydro-1h-cyclopenta[b]indol-7-yl] n-(2-phenylethyl)carbamate Chemical compound C=1C=C2N(C)C=3C(NCCN4CCOCC4)CCC=3C2=CC=1OC(=O)NCCC1=CC=CC=C1 MNLJJPCEPAYXFB-UHFFFAOYSA-N 0.000 description 1
- WTKJGTXNTSXOEQ-UHFFFAOYSA-N [4-methyl-3-(2-phenylethylimino)-1,2-dihydrocyclopenta[b]indol-7-yl] n-methylcarbamate Chemical compound C1CC=2C3=CC(OC(=O)NC)=CC=C3N(C)C=2C1=NCCC1=CC=CC=C1 WTKJGTXNTSXOEQ-UHFFFAOYSA-N 0.000 description 1
- QPZTZZIUHSHGSD-UHFFFAOYSA-N [5-bromo-3-(cyclopentylamino)-4-methyl-2,3,3a,4a,8a,8b-hexahydro-1h-cyclopenta[b]indol-7-yl] n-benzylcarbamate Chemical compound C1=C(Br)C2N(C)C3C(NC4CCCC4)CCC3C2C=C1OC(=O)NCC1=CC=CC=C1 QPZTZZIUHSHGSD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 229940082992 antihypertensives mao inhibitors Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000000035 biogenic effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 230000006949 cholinergic function Effects 0.000 description 1
- 230000000718 cholinopositive effect Effects 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 210000005257 cortical tissue Anatomy 0.000 description 1
- 229960003624 creatine Drugs 0.000 description 1
- 239000006046 creatine Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- CIISBNCSMVCNIP-UHFFFAOYSA-N cyclopentane-1,2-dione Chemical compound O=C1CCCC1=O CIISBNCSMVCNIP-UHFFFAOYSA-N 0.000 description 1
- BQGKKMWXHQPHKO-UHFFFAOYSA-N cyclopropanamine;1,2,3,4-tetrahydrocyclopenta[b]indole Chemical compound NC1CC1.N1C2=CC=CC=C2C2=C1CCC2 BQGKKMWXHQPHKO-UHFFFAOYSA-N 0.000 description 1
- INFZWTNREVTWIP-UHFFFAOYSA-N cyclopropanamine;4-methyl-2,3-dihydro-1h-cyclopenta[b]indole Chemical compound NC1CC1.C12=CC=CC=C2N(C)C2=C1CCC2 INFZWTNREVTWIP-UHFFFAOYSA-N 0.000 description 1
- 230000009615 deamination Effects 0.000 description 1
- 238000006481 deamination reaction Methods 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000012636 effector Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- SKHIBNDAFWIOPB-UHFFFAOYSA-N hydron;2-phenylethanamine;chloride Chemical compound Cl.NCCC1=CC=CC=C1 SKHIBNDAFWIOPB-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- LIRDJALZRPAZOR-UHFFFAOYSA-N indolin-3-one Chemical compound C1=CC=C2C(=O)CNC2=C1 LIRDJALZRPAZOR-UHFFFAOYSA-N 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000013101 initial test Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 208000003243 intestinal obstruction Diseases 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229940070023 iproniazide Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 206010027175 memory impairment Diseases 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 1
- 229940012189 methyl orange Drugs 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000002438 mitochondrial effect Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 206010028417 myasthenia gravis Diseases 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- MRDMFPPDURXXRI-UHFFFAOYSA-N n-cyclopropyl-1h-indol-2-amine Chemical compound C1CC1NC1=CC2=CC=CC=C2N1 MRDMFPPDURXXRI-UHFFFAOYSA-N 0.000 description 1
- SMEWATLYUJNDOM-UHFFFAOYSA-N n-cyclopropylaniline;hydrochloride Chemical compound Cl.C1CC1NC1=CC=CC=C1 SMEWATLYUJNDOM-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000001640 nerve ending Anatomy 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000001769 paralizing effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 229940048346 phenethylamine hydrochloride Drugs 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229960001697 physostigmine Drugs 0.000 description 1
- PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 description 1
- 229960001416 pilocarpine Drugs 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000003518 presynaptic effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000013014 purified material Substances 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical compound C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 210000003568 synaptosome Anatomy 0.000 description 1
- 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
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- LZSWRMIFVRYZMI-UHFFFAOYSA-N tert-butyl 3-oxo-1,2-dihydrocyclopenta[b]indole-4-carboxylate Chemical compound C12=CC=CC=C2N(C(=O)OC(C)(C)C)C2=C1CCC2=O LZSWRMIFVRYZMI-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 231100000048 toxicity data Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229960003741 tranylcypromine Drugs 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229960003732 tyramine Drugs 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Images
Classifications
-
- 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
-
- 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
- A61K31/403—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 condensed with carbocyclic rings, e.g. carbazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Psychiatry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US642952 | 1991-01-18 | ||
| US07/642,952 US5100891A (en) | 1991-01-18 | 1991-01-18 | Substituted 1,2,3,4-tetrahydrocyclopent[b]indoles, 1,2,3,3a,4,8a-hexahydrocyclopent[B]indoles and related compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2077530C1 true RU2077530C1 (ru) | 1997-04-20 |
Family
ID=24578739
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU925010763A RU2077530C1 (ru) | 1991-01-18 | 1992-01-17 | Замещенные тетрагидро-, или гексагидроциклопент /в/ индолы, или их фармацевтически приемлемые аддитивные соли и способы их получения |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US5100891A (OSRAM) |
| EP (1) | EP0496314B1 (OSRAM) |
| JP (1) | JP2665422B2 (OSRAM) |
| KR (1) | KR100230881B1 (OSRAM) |
| AT (1) | ATE158790T1 (OSRAM) |
| AU (1) | AU650315B2 (OSRAM) |
| BR (1) | BR9200171A (OSRAM) |
| CA (1) | CA2059610C (OSRAM) |
| CZ (1) | CZ282732B6 (OSRAM) |
| DE (1) | DE69222444T2 (OSRAM) |
| DK (1) | DK0496314T3 (OSRAM) |
| ES (1) | ES2109953T3 (OSRAM) |
| FI (2) | FI102174B (OSRAM) |
| GR (1) | GR3025318T3 (OSRAM) |
| HU (1) | HUT67027A (OSRAM) |
| IE (1) | IE920149A1 (OSRAM) |
| IL (1) | IL100693A0 (OSRAM) |
| MX (1) | MX9200206A (OSRAM) |
| NO (1) | NO178397C (OSRAM) |
| NZ (1) | NZ241305A (OSRAM) |
| PH (1) | PH31429A (OSRAM) |
| PL (2) | PL169417B1 (OSRAM) |
| RO (1) | RO112505B1 (OSRAM) |
| RU (1) | RU2077530C1 (OSRAM) |
| TW (1) | TW198024B (OSRAM) |
| ZA (1) | ZA92341B (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2225395C2 (ru) * | 1998-05-13 | 2004-03-10 | Солвей Фармасьютикалс Гмбх | Способ стереохимически контролируемого получения изомерно чистых высокозамещенных азациклических соединений |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5298626A (en) * | 1991-01-18 | 1994-03-29 | Hoechst-Roussel Pharmaceuticals Incorporated | Select cyclopent[b]indoles |
| US5350762A (en) * | 1993-03-08 | 1994-09-27 | Hoechst-Roussel Pharmaceuticals Incorporated | Tetrahydrocyclopent[B]indole methanamines and related compounds |
| US6172099B1 (en) * | 1997-07-03 | 2001-01-09 | Asahi Kasei Kogyo Kabushiki Kaisha | Tricyclic compounds having saturated rings and medicinal compositions containing the same |
| UA70334C2 (en) * | 1998-10-06 | 2004-10-15 | Janssen Pharmaceutica N V Jans | BENZOTHIENO[3,2-c]PYRIDINES AS a2 ANTAGONISTS BENZOTHIENO[3,2-c]PYRIDINES AS a2 ANTAGONISTS |
| UA69420C2 (uk) * | 1998-10-06 | 2004-09-15 | Янссен Фармацевтика Н.В. | ТРИЦИКЛІЧНІ <font face="Symbol">D3</font>-ПІПЕРИДИНИ ЯК <font face="Symbol">a<sub></font>2</sub>-АНТАГОНІСТИ |
| JP4590102B2 (ja) * | 1998-10-06 | 2010-12-01 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 医薬としての三環性δ３−ピペリジン類 |
| IT1317926B1 (it) | 2000-11-03 | 2003-07-15 | Sigma Tau Ind Farmaceuti | Derivati triciclici dell'indolo ad attivita' antiangiogenica. |
| EP1654228B1 (en) | 2003-06-10 | 2008-10-22 | Smithkline Beecham Corporation | Tetrahydrocarbazole derivatives and their pharmaceutical use |
| US7419997B2 (en) * | 2003-06-12 | 2008-09-02 | Smithkline Beecham Corporation | Tetrahydrocarbazole derivatives and their pharmaceutical use |
| JP2008520741A (ja) * | 2004-11-23 | 2008-06-19 | ピーティーシー セラピューティクス， インコーポレイテッド | 翻訳制御によるｖｅｇｆ生成を阻害するための活性因子としてのテトラヒドロカルバゾール |
| GB2422828A (en) * | 2005-02-03 | 2006-08-09 | Hunter Fleming Ltd | Tricyclic cytoprotective compounds comprising an indole residue |
| WO2013139929A1 (en) * | 2012-03-22 | 2013-09-26 | Ludwig-Maximilians-Universität München | Novel means and methods for treating diseases of the central nervous system, metabolic and cardiac diseases and aging |
| KR20140013471A (ko) | 2012-07-24 | 2014-02-05 | 주식회사 쎄코 | 진공증착용 발열조립체 및 이를 구비하는 진공증착장치 |
| US10882821B1 (en) | 2017-09-26 | 2021-01-05 | The Board Of Trustees Of The Leland Stanford Junior University | Enantiomeric compound for the reduction of the deleterious activity of extended nucleotide repeat containing genes |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3514462A (en) * | 1966-10-21 | 1970-05-26 | Upjohn Co | 1 and 2 ethoxy 3,4,5,10 - tetrahydroazepino(3,4-b) and (2,3-b)indoles and corresponding amino derivatives thereof |
| US3595874A (en) * | 1969-02-28 | 1971-07-27 | Upjohn Co | 3,4,5,10-tetrahydroazepino(2,3-b)indol-5a (2h)-ols |
| BE787537A (fr) * | 1971-08-16 | 1973-02-14 | Sterling Drug Inc | Tetrahydrocarbazoles |
| SU482086A1 (ru) * | 1973-11-30 | 1976-03-15 | Всесоюзный Научно-Исследовательски% Химико-Фармацевтический Институт Им.С.Орджоникидзе | Способ получени производных 1- -амино1,2,3,4-тетрагидрокарбазола |
| JPS5111760A (OSRAM) * | 1974-06-18 | 1976-01-30 | Ayerst Mckenna & Harrison | |
| US4254134A (en) * | 1978-03-17 | 1981-03-03 | Endo Laboratories, Inc. | Antidepressant 2-amino- and -2-(substituted amino)-cis-hexahydro-carbazoles |
-
1991
- 1991-01-18 US US07/642,952 patent/US5100891A/en not_active Expired - Lifetime
-
1992
- 1992-01-15 RO RO149168A patent/RO112505B1/ro unknown
- 1992-01-15 NZ NZ241305A patent/NZ241305A/en unknown
- 1992-01-16 PL PL92293209A patent/PL169417B1/pl unknown
- 1992-01-16 CZ CS92129A patent/CZ282732B6/cs not_active IP Right Cessation
- 1992-01-16 KR KR1019920000543A patent/KR100230881B1/ko not_active Expired - Fee Related
- 1992-01-16 PL PL92296651A patent/PL167465B1/pl unknown
- 1992-01-16 FI FI920192A patent/FI102174B/fi active
- 1992-01-17 IL IL100693A patent/IL100693A0/xx unknown
- 1992-01-17 RU SU925010763A patent/RU2077530C1/ru active
- 1992-01-17 AU AU10279/92A patent/AU650315B2/en not_active Ceased
- 1992-01-17 CA CA002059610A patent/CA2059610C/en not_active Expired - Lifetime
- 1992-01-17 NO NO920235A patent/NO178397C/no unknown
- 1992-01-17 JP JP4006681A patent/JP2665422B2/ja not_active Expired - Lifetime
- 1992-01-17 HU HU9200172A patent/HUT67027A/hu unknown
- 1992-01-17 IE IE014992A patent/IE920149A1/en not_active IP Right Cessation
- 1992-01-17 ZA ZA92341A patent/ZA92341B/xx unknown
- 1992-01-17 MX MX9200206A patent/MX9200206A/es unknown
- 1992-01-18 EP EP92100816A patent/EP0496314B1/en not_active Expired - Lifetime
- 1992-01-18 DE DE69222444T patent/DE69222444T2/de not_active Expired - Lifetime
- 1992-01-18 ES ES92100816T patent/ES2109953T3/es not_active Expired - Lifetime
- 1992-01-18 DK DK92100816.5T patent/DK0496314T3/da active
- 1992-01-18 AT AT92100816T patent/ATE158790T1/de not_active IP Right Cessation
- 1992-01-21 BR BR929200171A patent/BR9200171A/pt not_active Application Discontinuation
- 1992-02-20 TW TW081101228A patent/TW198024B/zh active
- 1992-11-20 PH PH43793A patent/PH31429A/en unknown
-
1997
- 1997-11-07 GR GR970402960T patent/GR3025318T3/el unknown
-
2000
- 2000-08-10 FI FI20001775A patent/FI107919B/fi active
Non-Patent Citations (1)
| Title |
|---|
| М.Д.Машковский. Лекарственные средства.- М.: Медицина, 1987, ч.1, с.96, 218 и 221. US, патент N 3931229, кл. C 07 D 209/04, 1976. * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2225395C2 (ru) * | 1998-05-13 | 2004-03-10 | Солвей Фармасьютикалс Гмбх | Способ стереохимически контролируемого получения изомерно чистых высокозамещенных азациклических соединений |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3159971B2 (ja) | 新規なジヒドロ及びテトラヒドロ−キノリン化合物、それらの製造方法ならびにそれらを含有する医薬組成物 | |
| CA2029265C (en) | 4- and 6-carbamates related to physostigmine, a process and intermediates for their preparation and their use as medicaments | |
| KR20030020954A (ko) | 피페라진 유도체 | |
| EP0496314B1 (en) | Substituted 1,2,3,4-tetrahydrocyclopent[b]indoles, 1,2,3,3a,4,8a-hexahydrocyclopent[b]indoles and related compounds, intermediates and a process for the preparation thereof and their use as medicaments | |
| EP0509400B1 (en) | 1-(Pyrido[3,4-b]-1,4-oxazinyl-4-yl)-1H-indoles, intermediates and a process for their preparation, and their use as medicaments | |
| JP2961013B2 (ja) | 〔（アリールアルキルピペリジン−４−イル）メチル〕−２ａ，３，４，５−テトラヒドロ−１（２Ｈ）−アセナフチレン−１−オン類および関連化合物 | |
| US5318967A (en) | 2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indole derivatives | |
| US5472975A (en) | Substituted 1,2,3,4-tetrahydrocyclopent[b]indoles, 1,2,3,3a,4,8a-hexahydrocyclopent[b]indoles and related compounds | |
| US5192789A (en) | Substituted 1,2,3,4-tetrahydrocyclopent[b]indoles, 1,2,3,3a,4,8a-hexahydrocyclopent[b]indoles and related compounds | |
| IE920459A1 (en) | 9-aminotetrahydroacridines and related compounds, a process¹for their preparation and their use as medicaments | |
| FI94759B (fi) | Menetelmä terapeuttisesti käyttökelpoisten 1,2,3,3a,8,8a-heksahydro-1,3a,8-trimetyylipyrrolo/2,3b/indolijohdannaisten valmistamiseksi | |
| JPH0720933B2 (ja) | インダノピロリジンカルバメート | |
| HUP9902755A2 (hu) | Spiro(ciklopent[b]indol-piperidin)-ek, intermedierek és gyógyszerkészítmények | |
| US5216164A (en) | 5-amino-5,6,7,8-tetrahydroquinolines and related compounds | |
| NZ245708A (en) | Physostigmine derivatives | |
| SI9200401A (en) | Indole derivatives |