NO301369B1 - 1-aminoetylindolderivater - Google Patents

1-aminoetylindolderivater Download PDF

Info

Publication number: NO301369B1
Authority: NO; Norway
Prior art keywords: mmol; solution; stirred; ether; chloro
Prior art date: 1993-10-22

Application number

NO943999A

Other languages

English (en)

Norwegian (no)

Other versions

NO943999L (no

NO943999D0 (no

Inventor

Michael Boes

Original Assignee

Hoffmann La Roche

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.)

1993-10-22

Filing date

1994-10-21

Publication date

1997-10-20

1994-10-21 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1994-10-21 Publication of NO943999D0 publication Critical patent/NO943999D0/no

1995-04-24 Publication of NO943999L publication Critical patent/NO943999L/no

1997-10-20 Publication of NO301369B1 publication Critical patent/NO301369B1/no

Links

150000001875 compounds Chemical class 0.000 claims description 73
239000001257 hydrogen Substances 0.000 claims description 40
229910052739 hydrogen Inorganic materials 0.000 claims description 40
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
239000002253 acid Substances 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
208000035475 disorder Diseases 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
208000006011 Stroke Diseases 0.000 claims description 5
229940126601 medicinal product Drugs 0.000 claims description 5
XJJZQXUGLLXTHO-ZETCQYMHSA-N (2S)-1-(6-chloro-5-fluoroindol-1-yl)-propan-2-amine Chemical compound FC1=C(Cl)C=C2N(C[C@@H](N)C)C=CC2=C1 XJJZQXUGLLXTHO-ZETCQYMHSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
208000019901 Anxiety disease Diseases 0.000 claims description 3
208000020925 Bipolar disease Diseases 0.000 claims description 3
208000032841 Bulimia Diseases 0.000 claims description 3
206010006550 Bulimia nervosa Diseases 0.000 claims description 3
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230000003542 behavioural effect Effects 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
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BJHBBPWFHWHWOG-SSDOTTSWSA-N (2r)-1-(4-chloro-5-fluoroindol-1-yl)propan-2-amine Chemical compound FC1=CC=C2N(C[C@H](N)C)C=CC2=C1Cl BJHBBPWFHWHWOG-SSDOTTSWSA-N 0.000 claims description 2
MYZDBEVPJGKIQS-SSDOTTSWSA-N (2r)-1-(5,6-difluoroindol-1-yl)propan-2-amine Chemical compound FC1=C(F)C=C2N(C[C@H](N)C)C=CC2=C1 MYZDBEVPJGKIQS-SSDOTTSWSA-N 0.000 claims description 2
DUUXOYARAAZWLV-MRVPVSSYSA-N (2r)-1-(5-fluoroindol-1-yl)propan-2-amine Chemical compound FC1=CC=C2N(C[C@H](N)C)C=CC2=C1 DUUXOYARAAZWLV-MRVPVSSYSA-N 0.000 claims description 2
XJJZQXUGLLXTHO-SSDOTTSWSA-N (2r)-1-(6-chloro-5-fluoroindol-1-yl)propan-2-amine Chemical compound FC1=C(Cl)C=C2N(C[C@H](N)C)C=CC2=C1 XJJZQXUGLLXTHO-SSDOTTSWSA-N 0.000 claims description 2
BJHBBPWFHWHWOG-ZETCQYMHSA-N (2s)-1-(4-chloro-5-fluoroindol-1-yl)propan-2-amine Chemical compound FC1=CC=C2N(C[C@@H](N)C)C=CC2=C1Cl BJHBBPWFHWHWOG-ZETCQYMHSA-N 0.000 claims description 2
YQZSYPKWHRXTCN-ZETCQYMHSA-N (2s)-1-[5-fluoro-4-(trifluoromethyl)indol-1-yl]propan-2-amine Chemical compound FC1=CC=C2N(C[C@@H](N)C)C=CC2=C1C(F)(F)F YQZSYPKWHRXTCN-ZETCQYMHSA-N 0.000 claims description 2
VGCXBJQGAKERIM-ZETCQYMHSA-N (2s)-1-[5-fluoro-6-(trifluoromethyl)indol-1-yl]propan-2-amine Chemical compound FC1=C(C(F)(F)F)C=C2N(C[C@@H](N)C)C=CC2=C1 VGCXBJQGAKERIM-ZETCQYMHSA-N 0.000 claims description 2
YMEHSPLPRQDLLW-UHFFFAOYSA-N 1-(4-methylindol-1-yl)propan-2-amine Chemical compound C1=CC=C2N(CC(N)C)C=CC2=C1C YMEHSPLPRQDLLW-UHFFFAOYSA-N 0.000 claims description 2
UOWVUNAMIYCETC-UHFFFAOYSA-N 1-(5-bromoindol-1-yl)propan-2-amine Chemical compound BrC1=CC=C2N(CC(N)C)C=CC2=C1 UOWVUNAMIYCETC-UHFFFAOYSA-N 0.000 claims description 2
XXCLNSYNUQMDML-UHFFFAOYSA-N 1-(5-chloroindol-1-yl)propan-2-amine Chemical compound ClC1=CC=C2N(CC(N)C)C=CC2=C1 XXCLNSYNUQMDML-UHFFFAOYSA-N 0.000 claims description 2
DUUXOYARAAZWLV-UHFFFAOYSA-N 1-(5-fluoroindol-1-yl)propan-2-amine Chemical compound FC1=CC=C2N(CC(N)C)C=CC2=C1 DUUXOYARAAZWLV-UHFFFAOYSA-N 0.000 claims description 2
XJJZQXUGLLXTHO-UHFFFAOYSA-N 1-(6-chloro-5-fluoroindol-1-yl)-propan-2-amine Chemical compound FC1=C(Cl)C=C2N(CC(N)C)C=CC2=C1 XJJZQXUGLLXTHO-UHFFFAOYSA-N 0.000 claims description 2
WZMZEXSQEAPONX-UHFFFAOYSA-N 1-(6-fluoroindol-1-yl)propan-2-amine Chemical compound C1=C(F)C=C2N(CC(N)C)C=CC2=C1 WZMZEXSQEAPONX-UHFFFAOYSA-N 0.000 claims description 2
MTKMOBVGAFBBKJ-UHFFFAOYSA-N 2-(4-chloro-5-fluoroindol-1-yl)ethanamine Chemical compound FC1=CC=C2N(CCN)C=CC2=C1Cl MTKMOBVGAFBBKJ-UHFFFAOYSA-N 0.000 claims description 2
HBDGGXQOJCCOCL-UHFFFAOYSA-N 2-(5-fluoro-3-methoxyindol-1-yl)ethanamine Chemical compound C1=C(F)C=C2C(OC)=CN(CCN)C2=C1 HBDGGXQOJCCOCL-UHFFFAOYSA-N 0.000 claims description 2
UEPNGPGBALZHNM-UHFFFAOYSA-N 2-(5-fluoroindol-1-yl)ethanamine Chemical compound FC1=CC=C2N(CCN)C=CC2=C1 UEPNGPGBALZHNM-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
208000018522 Gastrointestinal disease Diseases 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 2
MYZDBEVPJGKIQS-ZETCQYMHSA-N (2s)-1-(5,6-difluoroindol-1-yl)propan-2-amine Chemical compound FC1=C(F)C=C2N(C[C@@H](N)C)C=CC2=C1 MYZDBEVPJGKIQS-ZETCQYMHSA-N 0.000 claims 1
230000005176 gastrointestinal motility Effects 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 398
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 312
239000000243 solution Substances 0.000 description 276
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 135
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 133
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 123
239000002904 solvent Substances 0.000 description 122
229910052938 sodium sulfate Inorganic materials 0.000 description 120
235000011152 sodium sulphate Nutrition 0.000 description 120
239000012074 organic phase Substances 0.000 description 118
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 117
239000013078 crystal Substances 0.000 description 109
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 106
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 95
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 93
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 81
239000011541 reaction mixture Substances 0.000 description 81
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 75
239000000741 silica gel Substances 0.000 description 75
229910002027 silica gel Inorganic materials 0.000 description 75
239000008346 aqueous phase Substances 0.000 description 73
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 68
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
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239000000725 suspension Substances 0.000 description 58
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
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235000019198 oils Nutrition 0.000 description 42
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 42
239000001530 fumaric acid Substances 0.000 description 39
239000002585 base Substances 0.000 description 37
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
239000003054 catalyst Substances 0.000 description 34
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239000012312 sodium hydride Substances 0.000 description 32
229910000104 sodium hydride Inorganic materials 0.000 description 32
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239000006185 dispersion Substances 0.000 description 31
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QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 30
238000000354 decomposition reaction Methods 0.000 description 29
239000000203 mixture Substances 0.000 description 28
235000011121 sodium hydroxide Nutrition 0.000 description 22
239000012298 atmosphere Substances 0.000 description 21
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235000002639 sodium chloride Nutrition 0.000 description 20
238000001816 cooling Methods 0.000 description 18
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-1 methoxy, ethoxy, propoxy, isopropoxy Chemical group 0.000 description 14
239000012230 colorless oil Substances 0.000 description 13
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238000012360 testing method Methods 0.000 description 11
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PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 9
238000000034 method Methods 0.000 description 9
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239000012954 diazonium Substances 0.000 description 8
150000001989 diazonium salts Chemical class 0.000 description 8
238000001704 evaporation Methods 0.000 description 8
230000008020 evaporation Effects 0.000 description 8
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
150000002475 indoles Chemical class 0.000 description 7
239000012071 phase Substances 0.000 description 7
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WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
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239000005457 ice water Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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238000009835 boiling Methods 0.000 description 5
239000000839 emulsion Substances 0.000 description 5
239000007903 gelatin capsule Substances 0.000 description 5
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108020003175 receptors Proteins 0.000 description 5
102000005962 receptors Human genes 0.000 description 5
TUYZSKJQXNCPLN-UHFFFAOYSA-N 4-chloro-5-fluoro-1h-indole Chemical compound FC1=CC=C2NC=CC2=C1Cl TUYZSKJQXNCPLN-UHFFFAOYSA-N 0.000 description 4
ANGRSSWNBDJESO-UHFFFAOYSA-N 6-chloro-5-fluoro-1h-indole Chemical compound C1=C(Cl)C(F)=CC2=C1NC=C2 ANGRSSWNBDJESO-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
229940054051 antipsychotic indole derivative Drugs 0.000 description 4
229910052786 argon Inorganic materials 0.000 description 4
OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 4
239000003446 ligand Substances 0.000 description 4
239000000825 pharmaceutical preparation Substances 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
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CEPHEXXZGQBXGT-XZTIXWOLSA-N (e)-but-2-enedioic acid;(2s)-1-(6-chloro-5-fluoroindol-1-yl)propan-2-amine Chemical compound OC(=O)\C=C\C(O)=O.FC1=C(Cl)C=C2N(C[C@@H](N)C)C=CC2=C1 CEPHEXXZGQBXGT-XZTIXWOLSA-N 0.000 description 3
FKKWFQULHCAHAQ-UHFFFAOYSA-N 3-methoxy-4-methyl-1h-indole-2-carboxylic acid Chemical compound C1=CC(C)=C2C(OC)=C(C(O)=O)NC2=C1 FKKWFQULHCAHAQ-UHFFFAOYSA-N 0.000 description 3
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ONYNOPPOVKYGRS-UHFFFAOYSA-N 6-methyl-1h-indole Chemical compound CC1=CC=C2C=CNC2=C1 ONYNOPPOVKYGRS-UHFFFAOYSA-N 0.000 description 3
239000002168 alkylating agent Substances 0.000 description 3
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238000003776 cleavage reaction Methods 0.000 description 3
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230000004992 fission Effects 0.000 description 3
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230000018052 penile erection Effects 0.000 description 3
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125000001424 substituent group Chemical group 0.000 description 3
FLUDLQYYIYREOO-UHFFFAOYSA-N (1-acetyl-2-chloro-5-fluoroindol-3-yl) acetate Chemical compound C1=C(F)C=C2C(OC(=O)C)=C(Cl)N(C(C)=O)C2=C1 FLUDLQYYIYREOO-UHFFFAOYSA-N 0.000 description 2
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HTJADBYJFSTXCC-SNVBAGLBSA-N (2r)-1-(3-methoxy-4-methylindol-1-yl)propan-2-ol Chemical compound C1=CC(C)=C2C(OC)=CN(C[C@@H](C)O)C2=C1 HTJADBYJFSTXCC-SNVBAGLBSA-N 0.000 description 2
BZFWKWJIXXNMDH-MRVPVSSYSA-N (2r)-1-(4-chloro-3-ethyl-5-fluoroindol-1-yl)propan-2-ol Chemical compound C1=C(F)C(Cl)=C2C(CC)=CN(C[C@@H](C)O)C2=C1 BZFWKWJIXXNMDH-MRVPVSSYSA-N 0.000 description 2
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CURQWZKBAVHJPH-UHFFFAOYSA-N 6-chloro-5-fluoro-3-methyl-1h-indole Chemical compound ClC1=C(F)C=C2C(C)=CNC2=C1 CURQWZKBAVHJPH-UHFFFAOYSA-N 0.000 description 1
YYFFEPUCAKVRJX-UHFFFAOYSA-N 6-fluoro-1h-indole Chemical compound FC1=CC=C2C=CNC2=C1 YYFFEPUCAKVRJX-UHFFFAOYSA-N 0.000 description 1
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NJFIQCOFOZNSSU-UHFFFAOYSA-N 7-chloro-6-fluoro-1h-indole-2-carboxylic acid Chemical compound C1=C(F)C(Cl)=C2NC(C(=O)O)=CC2=C1 NJFIQCOFOZNSSU-UHFFFAOYSA-N 0.000 description 1
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
HWNWEADNYVHQDS-FVGYRXGTSA-N C(C=CC(=O)O)(=O)O.C(C)C1=CN(C2=CC=C(C=C12)F)C[C@H](C)N Chemical compound C(C=CC(=O)O)(=O)O.C(C)C1=CN(C2=CC=C(C=C12)F)C[C@H](C)N HWNWEADNYVHQDS-FVGYRXGTSA-N 0.000 description 1
QAWLJAUWZHXYMQ-UHFFFAOYSA-N C(C=CC(=O)O)(=O)O.CNCC Chemical compound C(C=CC(=O)O)(=O)O.CNCC QAWLJAUWZHXYMQ-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
238000006783 Fischer indole synthesis reaction Methods 0.000 description 1
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CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
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235000021355 Stearic acid Nutrition 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 1
MOQOOKGPCBQMCY-UHFFFAOYSA-N acetic acid;hexane Chemical compound CC(O)=O.CCCCCC MOQOOKGPCBQMCY-UHFFFAOYSA-N 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
150000003934 aromatic aldehydes Chemical class 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
239000000872 buffer Substances 0.000 description 1
244000309464 bull Species 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000003431 cross linking reagent Substances 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
201000010099 disease Diseases 0.000 description 1
230000006806 disease prevention Effects 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
KKJPCLMOJKUILK-UHFFFAOYSA-N ethyl 3-methoxy-4-methyl-1h-indole-2-carboxylate Chemical compound C1=CC(C)=C2C(OC)=C(C(=O)OCC)NC2=C1 KKJPCLMOJKUILK-UHFFFAOYSA-N 0.000 description 1
OVSOYWROLOCQIS-UHFFFAOYSA-N ethyl 5,6-difluoro-1h-indole-2-carboxylate Chemical compound FC1=C(F)C=C2NC(C(=O)OCC)=CC2=C1 OVSOYWROLOCQIS-UHFFFAOYSA-N 0.000 description 1
KSJIULFYLRMPAD-UHFFFAOYSA-N ethyl 5-fluoro-4-(trifluoromethyl)-1h-indole-2-carboxylate Chemical compound FC1=CC=C2NC(C(=O)OCC)=CC2=C1C(F)(F)F KSJIULFYLRMPAD-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000796 flavoring agent 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
239000012362 glacial acetic acid Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
HCUARRIEZVDMPT-UHFFFAOYSA-N indolyl-2-carboxylic acid Natural products C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
208000028774 intestinal disease Diseases 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229960005417 ketanserin Drugs 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
RXYCUKSOYJWGPE-UHFFFAOYSA-N methyl 2-azidoacetate Chemical compound COC(=O)CN=[N+]=[N-] RXYCUKSOYJWGPE-UHFFFAOYSA-N 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
206010027599 migraine Diseases 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 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
239000010502 orange oil 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
150000002924 oxiranes Chemical class 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
238000003408 phase transfer catalysis Methods 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000008569 process Effects 0.000 description 1
239000002287 radioligand Substances 0.000 description 1
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239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
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208000018556 stomach disease Diseases 0.000 description 1
208000023516 stroke disease Diseases 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
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239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000001149 thermolysis Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
239000002966 varnish Substances 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1

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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/36—Oxygen atoms in position 3, e.g. adrenochrome
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- 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
- 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
- A61P25/06—Antimigraine agents
- A—HUMAN NECESSITIES
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Hospice & Palliative Care (AREA)
Hematology (AREA)
Diabetes (AREA)
Anesthesiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Organic Insulating Materials (AREA)
Materials For Medical Uses (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

NO943999A 1993-10-22 1994-10-21 1-aminoetylindolderivater NO301369B1 (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH320193		1993-10-22

Publications (3)

Publication Number	Publication Date
NO943999D0 NO943999D0 (no)	1994-10-21
NO943999L NO943999L (no)	1995-04-24
NO301369B1 true NO301369B1 (no)	1997-10-20

Family

ID=4250849

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO943999A NO301369B1 (no)	1993-10-22	1994-10-21	1-aminoetylindolderivater

Country Status (19)

Country	Link
US (1)	US5494928A (th)
EP (1)	EP0655440A3 (th)
JP (1)	JP2638752B2 (th)
KR (1)	KR950011406A (th)
CN (1)	CN1061341C (th)
AU (1)	AU685841B2 (th)
BR (1)	BR9404203A (th)
CA (1)	CA2132883A1 (th)
CO (1)	CO4290356A1 (th)
CZ (1)	CZ260494A3 (th)
FI (1)	FI944969A7 (th)
HU (1)	HU218669B (th)
IL (1)	IL111314A (th)
NO (1)	NO301369B1 (th)
NZ (1)	NZ264713A (th)
PL (1)	PL179561B1 (th)
RU (1)	RU2136662C1 (th)
TW (1)	TW270114B (th)
ZA (1)	ZA948094B (th)

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AU717422B2 (en) *	1995-09-01	2000-03-23	Eli Lilly And Company	Indolyl neuropeptide Y receptor antagonists
AU3255697A (en) *	1996-06-12	1998-01-07	F. Hoffmann-La Roche Ag	A process for the manufacture of 1-(amino-alkyl)-indoles
AU727654B2 (en)	1997-06-13	2000-12-21	Yamanouchi Pharmaceutical Co., Ltd.	Tricyclic pyrazole derivative
ES2267190T3 (es) *	1997-08-07	2007-03-01	Fujimoto Brothers Co., Ltd.	Derivados de etilamina novedosos.
US6960579B1 (en)	1998-05-19	2005-11-01	Alcon Manufacturing, Ltd.	Serotonergic 5HT7 receptor compounds for treating ocular and CNS disorders
ES2257869T3 (es) *	1998-08-21	2006-08-01	Novartis Ag	Nueva formulacion oral para agonistas o antagonistas de 5-ht4.
GB9819019D0 (en) *	1998-09-01	1998-10-28	Cerebrus Ltd	Chemical compounds II
GB9819032D0 (en) *	1998-09-01	1998-10-28	Cerebrus Ltd	Chemical compounds IV
GB9819033D0 (en) *	1998-09-01	1998-10-28	Cerebrus Ltd	Chemical compounds VI
US6326379B1 (en)	1998-09-16	2001-12-04	Bristol-Myers Squibb Co.	Fused pyridine inhibitors of cGMP phosphodiesterase
DK1112106T3 (da)	1998-09-18	2005-12-12	Alcon Mfg Ltd	Serotonerge 5HT2-agonister til behandling af glaukom
FR2788772B1 (fr) *	1999-01-26	2001-03-02	Adir	Nouveaux composes cyano-indoles inhibiteurs de recapture de serotonine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
FR2792313A1 (fr) *	1999-04-13	2000-10-20	Synthelabo	Derives de 2-aminoethyl-indole, leur preparation et leur application en therapeutique
US6465467B1 (en)	1999-05-21	2002-10-15	Biovitrum Ab	Certain aryl-aliphatic and heteroaryl-aliphatic piperazinyl pyrazines and their use in the treatment of serotonin-related diseases
GB9918965D0 (en) *	1999-08-11	1999-10-13	Cerebrus Ltd	Chemical compounds xxi
GB9918962D0 (en)	1999-08-11	1999-10-13	Cerebrus Ltd	Chemical compounds xxii
HK1048801B (en) *	1999-11-05	2009-08-28	Emisphere Technologies, Inc.	Phenoxy carboxylic acid compounds and compositions for delivering active agents
WO2001040183A1 (en) *	1999-12-03	2001-06-07	Alcon Universal Ltd.	1-aminoalkyl-1h-indoles for treating glaucoma
JP3585796B2 (ja)	1999-12-17	2004-11-04	新光電気工業株式会社	多層配線基板の製造方法、及び半導体装置
DE19963178A1 (de) *	1999-12-27	2001-07-05	Gruenenthal Gmbh	Substituierte Indol-Mannichbasen
EP1132389A1 (en)	2000-03-06	2001-09-12	Vernalis Research Limited	New aza-indolyl derivatives for the treatment of obesity
US6806285B1 (en)	2000-03-17	2004-10-19	Alcon, Inc.	5-Hydroxyl indole derivatives for treating glaucoma
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- 1994-09-21 CA CA002132883A patent/CA2132883A1/en not_active Abandoned
- 1994-10-03 US US08/317,259 patent/US5494928A/en not_active Expired - Fee Related
- 1994-10-07 EP EP94115800A patent/EP0655440A3/de not_active Withdrawn
- 1994-10-14 ZA ZA948094A patent/ZA948094B/xx unknown
- 1994-10-14 AU AU75837/94A patent/AU685841B2/en not_active Ceased
- 1994-10-17 HU HU9402983A patent/HU218669B/hu not_active IP Right Cessation
- 1994-10-17 IL IL11131494A patent/IL111314A/xx not_active IP Right Cessation
- 1994-10-17 NZ NZ264713A patent/NZ264713A/en unknown
- 1994-10-19 CO CO94047587A patent/CO4290356A1/es unknown
- 1994-10-20 CN CN94117149A patent/CN1061341C/zh not_active Expired - Fee Related
- 1994-10-20 RU RU94037964A patent/RU2136662C1/ru active
- 1994-10-21 FI FI944969A patent/FI944969A7/fi unknown
- 1994-10-21 PL PL94305543A patent/PL179561B1/pl unknown
- 1994-10-21 NO NO943999A patent/NO301369B1/no not_active IP Right Cessation
- 1994-10-21 BR BR9404203A patent/BR9404203A/pt not_active Application Discontinuation
- 1994-10-21 CZ CZ942604A patent/CZ260494A3/cs unknown
- 1994-10-22 KR KR1019940027045A patent/KR950011406A/ko not_active Ceased
- 1994-10-24 JP JP6257775A patent/JP2638752B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CZ260494A3 (en)	1995-10-18
US5494928A (en)	1996-02-27
PL305543A1 (en)	1995-05-02
HU9402983D0 (en)	1995-02-28
FI944969A0 (fi)	1994-10-21
JPH07149723A (ja)	1995-06-13
AU685841B2 (en)	1998-01-29
AU7583794A (en)	1995-05-11
CN1061341C (zh)	2001-01-31
BR9404203A (pt)	1995-07-04
FI944969A7 (fi)	1995-04-23
NZ264713A (en)	1996-05-28
TW270114B (th)	1996-02-11
ZA948094B (en)	1995-04-24
CA2132883A1 (en)	1995-04-23
HUT70848A (en)	1995-11-28
RU94037964A (ru)	1996-09-10
NO943999L (no)	1995-04-24
IL111314A0 (en)	1994-12-29
IL111314A (en)	1999-08-17
EP0655440A2 (de)	1995-05-31
KR950011406A (ko)	1995-05-15
JP2638752B2 (ja)	1997-08-06
NO943999D0 (no)	1994-10-21
RU2136662C1 (ru)	1999-09-10
CO4290356A1 (es)	1996-04-17
CN1105988A (zh)	1995-08-02
HU218669B (hu)	2000-10-28
PL179561B1 (pl)	2000-09-29
EP0655440A3 (de)	1996-11-06

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