SI9200401A - Indole derivatives - Google Patents

Indole derivatives Download PDF

Info

Publication number: SI9200401A
Authority: SI; Slovenia
Prior art keywords: cis; hexahydro; benzo; rac; indol
Prior art date: 1991-12-20

Application number

SI9200401A

Other languages

English (en)

Slovenian (sl)

Inventor

Hans Bruderer

Thierry Godel

Rene Imhof

Roland Jakob-Roetne

Original Assignee

F.Hoffmann-La Roche Ag

Priority date (The priority date 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 date listed.)

1991-12-20

Filing date

1992-12-18

Publication date

1993-06-30

1992-12-18 Application filed by F.Hoffmann-La Roche Ag filed Critical F.Hoffmann-La Roche Ag

1993-06-30 Publication of SI9200401A publication Critical patent/SI9200401A/sl

Links

229940054051 antipsychotic indole derivative Drugs 0.000 title description 2
150000002475 indoles Chemical class 0.000 title description 2
-1 or a cyclic amino Chemical group 0.000 claims description 186
239000000203 mixture Substances 0.000 claims description 149
150000001875 compounds Chemical class 0.000 claims description 51
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 27
JEYXDYNMDRWXJC-UHFFFAOYSA-N CN(C)C(=O)OC1=CC=C2C=CNC2=C1 Chemical compound CN(C)C(=O)OC1=CC=C2C=CNC2=C1 JEYXDYNMDRWXJC-UHFFFAOYSA-N 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 22
125000003277 amino group Chemical group 0.000 claims description 18
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 17
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 claims description 17
208000024827 Alzheimer disease Diseases 0.000 claims description 16
238000002360 preparation method Methods 0.000 claims description 16
239000003814 drug Substances 0.000 claims description 11
238000011282 treatment Methods 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims description 8
206010039966 Senile dementia Diseases 0.000 claims description 8
208000010877 cognitive disease Diseases 0.000 claims description 8
238000000034 method Methods 0.000 claims description 8
238000011321 prophylaxis Methods 0.000 claims description 8
125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 claims description 7
208000028698 Cognitive impairment Diseases 0.000 claims description 7
GXMHAHSLRYIDHI-CTNGQTDRSA-N [(3as,9br)-3-(2-cyclohexylethyl)-1,2,3a,4,5,9b-hexahydrobenzo[e]indol-6-yl] n,n-dimethylcarbamate Chemical compound C([C@@H]1C=2C=CC=C(C=2CC[C@@H]11)OC(=O)N(C)C)CN1CCC1CCCCC1 GXMHAHSLRYIDHI-CTNGQTDRSA-N 0.000 claims description 7
230000006386 memory function Effects 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 6
125000003435 aroyl group Chemical group 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000004122 cyclic group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000005462 imide group Chemical group 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 3
125000005239 aroylamino group Chemical group 0.000 claims description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
229940124597 therapeutic agent Drugs 0.000 claims description 3
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 2
CNEZOJQYCFNQKG-QUCCMNQESA-N C([C@@H]1C=2C=CC=C(C=2CC[C@@H]11)OC(=O)N(C)C)CN1CCC1CCCC1 Chemical compound C([C@@H]1C=2C=CC=C(C=2CC[C@@H]11)OC(=O)N(C)C)CN1CCC1CCCC1 CNEZOJQYCFNQKG-QUCCMNQESA-N 0.000 claims description 2
WQGUVJBQDCBCNN-IRLDBZIGSA-N C([C@@H]1C=2C=CC=C(C=2CC[C@@H]11)OC(=O)N(C)C)CN1CCCC1CCCCC1 Chemical compound C([C@@H]1C=2C=CC=C(C=2CC[C@@H]11)OC(=O)N(C)C)CN1CCCC1CCCCC1 WQGUVJBQDCBCNN-IRLDBZIGSA-N 0.000 claims description 2
LMWGNKLLLBEJLC-GJZGRUSLSA-N CN(C(OC1=CC=CC2=C1[C@H]1CCN([C@H]1CC2)CCC)=O)C Chemical compound CN(C(OC1=CC=CC2=C1[C@H]1CCN([C@H]1CC2)CCC)=O)C LMWGNKLLLBEJLC-GJZGRUSLSA-N 0.000 claims description 2
ZFRRYMKUWNBSPT-MJGOQNOKSA-N [(3aS,9bR)-3-(2-morpholin-4-ylethyl)-1,2,3a,4,5,9b-hexahydrobenzo[e]indol-6-yl] N,N-dimethylcarbamate Chemical compound CN(C(OC1=CC=CC=2[C@H]3CCN([C@H]3CCC21)CCN2CCOCC2)=O)C ZFRRYMKUWNBSPT-MJGOQNOKSA-N 0.000 claims description 2
DBBAFYGKBOIGJL-GGAORHGYSA-N [(3aS,9bR)-3-(4-cyclohexylbutyl)-1,2,3a,4,5,9b-hexahydrobenzo[e]indol-6-yl] N,N-dimethylcarbamate Chemical compound CN(C(OC1=CC=CC=2[C@H]3CCN([C@H]3CCC21)CCCCC2CCCCC2)=O)C DBBAFYGKBOIGJL-GGAORHGYSA-N 0.000 claims description 2
BFIWCHOUWQIZIO-BWKNWUBXSA-N [(3aS,9bR)-3-[6-(1,3-dioxoisoindol-2-yl)hexyl]-1,2,3a,4,5,9b-hexahydrobenzo[e]indol-6-yl] N,N-dimethylcarbamate Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCCCCCN1CC[C@@H]2C(C=CC=C3OC(=O)N(C)C)=C3CC[C@@H]21 BFIWCHOUWQIZIO-BWKNWUBXSA-N 0.000 claims description 2
HUGQDDJXYKRDAL-QUCCMNQESA-N [(3as,9br)-3-(2-cyclohexylethyl)-1,2,3a,4,5,9b-hexahydrobenzo[e]indol-6-yl] n-methylcarbamate Chemical compound C([C@@H]1C=2C=CC=C(C=2CC[C@@H]11)OC(=O)NC)CN1CCC1CCCCC1 HUGQDDJXYKRDAL-QUCCMNQESA-N 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
LTZITRRKIWUGOD-UHFFFAOYSA-N CCCNC(=O)OC1=CC=C2C=CNC2=C1 Chemical compound CCCNC(=O)OC1=CC=C2C=CNC2=C1 LTZITRRKIWUGOD-UHFFFAOYSA-N 0.000 claims 1
AARBHABYRMRLNI-IRLDBZIGSA-N [(3as,9br)-3-(2-cyclohexylethyl)-1,2,3a,4,5,9b-hexahydrobenzo[e]indol-6-yl] n-ethyl-n-methylcarbamate Chemical compound C([C@@H]1C=2C=CC=C(C=2CC[C@@H]11)OC(=O)N(C)CC)CN1CCC1CCCCC1 AARBHABYRMRLNI-IRLDBZIGSA-N 0.000 claims 1
125000003368 amide group Chemical group 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 465
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 306
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 291
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 243
239000000243 solution Substances 0.000 description 212
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 198
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 180
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 118
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 117
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 116
239000000741 silica gel Substances 0.000 description 113
229910002027 silica gel Inorganic materials 0.000 description 113
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 111
239000013078 crystal Substances 0.000 description 110
238000010992 reflux Methods 0.000 description 101
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 92
239000003921 oil Substances 0.000 description 91
235000019198 oils Nutrition 0.000 description 91
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 82
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 79
229910052938 sodium sulfate Inorganic materials 0.000 description 79
235000011152 sodium sulphate Nutrition 0.000 description 79
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 77
239000002585 base Substances 0.000 description 77
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 77
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 76
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 73
238000001704 evaporation Methods 0.000 description 66
239000012074 organic phase Substances 0.000 description 65
DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 63
238000004587 chromatography analysis Methods 0.000 description 58
230000008020 evaporation Effects 0.000 description 58
235000017557 sodium bicarbonate Nutrition 0.000 description 58
229910000030 sodium bicarbonate Inorganic materials 0.000 description 58
239000002904 solvent Substances 0.000 description 54
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 51
229920006395 saturated elastomer Polymers 0.000 description 46
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 45
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 41
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 38
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 34
125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 33
238000001035 drying Methods 0.000 description 32
239000007787 solid Substances 0.000 description 32
238000001914 filtration Methods 0.000 description 29
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 28
YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 26
235000019439 ethyl acetate Nutrition 0.000 description 25
239000011780 sodium chloride Substances 0.000 description 25
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
239000000047 product Substances 0.000 description 24
239000000725 suspension Substances 0.000 description 24
238000001816 cooling Methods 0.000 description 23
239000000284 extract Substances 0.000 description 22
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 21
239000000463 material Substances 0.000 description 20
XAWPKHNOFIWWNZ-UHFFFAOYSA-N 1h-indol-6-ol Chemical compound OC1=CC=C2C=CNC2=C1 XAWPKHNOFIWWNZ-UHFFFAOYSA-N 0.000 description 19
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 19
229910052786 argon Inorganic materials 0.000 description 19
239000012280 lithium aluminium hydride Substances 0.000 description 19
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
239000000706 filtrate Substances 0.000 description 18
239000007832 Na2SO4 Substances 0.000 description 17
229910052943 magnesium sulfate Inorganic materials 0.000 description 17
235000019341 magnesium sulphate Nutrition 0.000 description 17
238000002425 crystallisation Methods 0.000 description 16
230000008025 crystallization Effects 0.000 description 16
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 16
MLYIUHOUXKYDNT-PWSUYJOCSA-N (3aS,9bR)-6-methoxy-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indole Chemical compound COC1=CC=CC=2[C@H]3CCN[C@H]3CCC21 MLYIUHOUXKYDNT-PWSUYJOCSA-N 0.000 description 15
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
239000006260 foam Substances 0.000 description 15
HDPXRRBHNJGDJG-UHFFFAOYSA-N Cl.CN(C(=O)OC1=CC=C2C=CNC2=C1)C Chemical compound Cl.CN(C(=O)OC1=CC=C2C=CNC2=C1)C HDPXRRBHNJGDJG-UHFFFAOYSA-N 0.000 description 14
239000007868 Raney catalyst Substances 0.000 description 14
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 14
229910000564 Raney nickel Inorganic materials 0.000 description 14
239000007864 aqueous solution Substances 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 14
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 13
235000011114 ammonium hydroxide Nutrition 0.000 description 13
238000001953 recrystallisation Methods 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 12
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 12
238000000354 decomposition reaction Methods 0.000 description 12
ZGBUJKAZQOPWGZ-UHFFFAOYSA-N ethyl 2-(5-methoxy-2-oxo-3,4-dihydro-1h-naphthalen-1-yl)acetate Chemical compound C1=CC=C2C(CC(=O)OCC)C(=O)CCC2=C1OC ZGBUJKAZQOPWGZ-UHFFFAOYSA-N 0.000 description 12
239000002244 precipitate Substances 0.000 description 12
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
DWLVWMUCHSLGSU-UHFFFAOYSA-M n,n-dimethylcarbamate Chemical compound CN(C)C([O-])=O DWLVWMUCHSLGSU-UHFFFAOYSA-M 0.000 description 11
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 10
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
239000011734 sodium Substances 0.000 description 10
238000000605 extraction Methods 0.000 description 9
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
235000019270 ammonium chloride Nutrition 0.000 description 8
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 8
239000012230 colorless oil Substances 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 7
235000009518 sodium iodide Nutrition 0.000 description 7
239000000126 substance Substances 0.000 description 7
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 6
QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 6
239000007903 gelatin capsule Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 5
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 5
229920000168 Microcrystalline cellulose Polymers 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
230000010933 acylation Effects 0.000 description 5
238000005917 acylation reaction Methods 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
239000012267 brine Substances 0.000 description 5
239000002775 capsule Substances 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
238000004821 distillation Methods 0.000 description 5
235000019359 magnesium stearate Nutrition 0.000 description 5
239000008108 microcrystalline cellulose Substances 0.000 description 5
235000019813 microcrystalline cellulose Nutrition 0.000 description 5
229940016286 microcrystalline cellulose Drugs 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000002689 soil Substances 0.000 description 5
238000006467 substitution reaction Methods 0.000 description 5
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
AJBWNNKDUMXZLM-UHFFFAOYSA-N 4-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=C(C(O)=O)C=C1 AJBWNNKDUMXZLM-UHFFFAOYSA-N 0.000 description 4
ZJWHUBXRWMBSMV-UHFFFAOYSA-N Cl.OC1=CC=C2C=CNC2=C1 Chemical compound Cl.OC1=CC=C2C=CNC2=C1 ZJWHUBXRWMBSMV-UHFFFAOYSA-N 0.000 description 4
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 4
229960004373 acetylcholine Drugs 0.000 description 4
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 description 4
PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 4
239000012452 mother liquor Substances 0.000 description 4
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HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
239000000539 dimer Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000002329 esterase inhibitor Substances 0.000 description 1
UWRZJQUXJAOASA-UHFFFAOYSA-N ethyl 2-(8-methoxy-2-oxo-3,4-dihydro-1H-naphthalen-1-yl)acetate Chemical compound COC=1C=CC=C2CCC(C(C=12)CC(=O)OCC)=O UWRZJQUXJAOASA-UHFFFAOYSA-N 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
239000003925 fat Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
150000004674 formic acids Chemical class 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229960004903 invert sugar Drugs 0.000 description 1
JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 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
150000002576 ketones Chemical class 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
239000000155 melt Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
239000000472 muscarinic agonist Substances 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
XZVYDRLPXWFRIS-UHFFFAOYSA-N n-ethyl-n-methylcarbamoyl chloride Chemical compound CCN(C)C(Cl)=O XZVYDRLPXWFRIS-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000012053 oil suspension Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000013618 particulate matter Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
229960001697 physostigmine Drugs 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
150000003254 radicals Chemical group 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
230000007017 scission Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
241000894007 species Species 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
231100000048 toxicity data Toxicity 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
UGKSITLWMZJTHC-UHFFFAOYSA-N tribromo-$l^{3}-bromane Chemical compound BrBr(Br)Br UGKSITLWMZJTHC-UHFFFAOYSA-N 0.000 description 1
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)

SI9200401A 1991-12-20 1992-12-18 Indole derivatives SI9200401A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH380691		1991-12-20

Publications (1)

Publication Number	Publication Date
SI9200401A true SI9200401A (en)	1993-06-30

Family

ID=4263855

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SI9200401A SI9200401A (en)	1991-12-20	1992-12-18	Indole derivatives

Country Status (8)

Country	Link
BR (1)	BR9205031A (sr)
HR (1)	HRP921448A2 (sr)
MX (1)	MX9207333A (sr)
PL (1)	PL297066A1 (sr)
SI (1)	SI9200401A (sr)
UY (1)	UY23524A1 (sr)
YU (1)	YU9893A (sr)
ZA (1)	ZA929875B (sr)

1992
- 1992-12-16 MX MX9207333A patent/MX9207333A/es not_active IP Right Cessation
- 1992-12-16 BR BR9205031A patent/BR9205031A/pt not_active Application Discontinuation
- 1992-12-18 HR HRP921448 patent/HRP921448A2/xx not_active Application Discontinuation
- 1992-12-18 ZA ZA929875A patent/ZA929875B/xx unknown
- 1992-12-18 SI SI9200401A patent/SI9200401A/sl unknown
- 1992-12-18 UY UY23524A patent/UY23524A1/es unknown
- 1992-12-18 PL PL29706692A patent/PL297066A1/xx unknown
1993
- 1993-02-15 YU YU9893A patent/YU9893A/sr unknown

Also Published As

Publication number	Publication date
UY23524A1 (es)	1993-06-11
ZA929875B (en)	1994-03-22
HRP921448A2 (en)	1996-10-31
PL297066A1 (en)	1993-08-23
BR9205031A (pt)	1993-06-22
YU9893A (sr)	1996-01-09
MX9207333A (es)	1993-11-01

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US5292761A (en)	1994-03-08	Piperidine, tetrahydropyridine and pyrrolidine compounds
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US4153789A (en)	1979-05-08	Phenylindolines
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US3621027A (en)	1971-11-16	1-aminoalkyl-2,6-diaryl 4,5,6,7 tetrahydro-4-oxindales
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