CA2132883A1 - 1-amino-ethylindole-derivatives - Google Patents
1-amino-ethylindole-derivativesInfo
- Publication number
- CA2132883A1 CA2132883A1 CA002132883A CA2132883A CA2132883A1 CA 2132883 A1 CA2132883 A1 CA 2132883A1 CA 002132883 A CA002132883 A CA 002132883A CA 2132883 A CA2132883 A CA 2132883A CA 2132883 A1 CA2132883 A1 CA 2132883A1
- Authority
- CA
- Canada
- Prior art keywords
- disorders
- mmol
- indol
- fluoro
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 84
- 239000001257 hydrogen Substances 0.000 claims abstract description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 43
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 37
- 239000002253 acid Substances 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 19
- 208000035475 disorder Diseases 0.000 claims abstract description 19
- 208000002193 Pain Diseases 0.000 claims abstract description 14
- 208000006011 Stroke Diseases 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 230000002265 prevention Effects 0.000 claims abstract description 8
- 238000011282 treatment Methods 0.000 claims abstract description 8
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 7
- 208000020925 Bipolar disease Diseases 0.000 claims abstract description 7
- 208000032841 Bulimia Diseases 0.000 claims abstract description 7
- 206010006550 Bulimia nervosa Diseases 0.000 claims abstract description 7
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 7
- 206010012335 Dependence Diseases 0.000 claims abstract description 7
- 208000020401 Depressive disease Diseases 0.000 claims abstract description 7
- 208000018522 Gastrointestinal disease Diseases 0.000 claims abstract description 7
- 208000019695 Migraine disease Diseases 0.000 claims abstract description 7
- 208000008589 Obesity Diseases 0.000 claims abstract description 7
- 208000028017 Psychotic disease Diseases 0.000 claims abstract description 7
- 206010041250 Social phobia Diseases 0.000 claims abstract description 7
- 208000007536 Thrombosis Diseases 0.000 claims abstract description 7
- 208000014674 injury Diseases 0.000 claims abstract description 7
- 206010027599 migraine Diseases 0.000 claims abstract description 7
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 7
- 235000020824 obesity Nutrition 0.000 claims abstract description 7
- 208000012201 sexual and gender identity disease Diseases 0.000 claims abstract description 7
- 208000015891 sexual disease Diseases 0.000 claims abstract description 7
- 208000019116 sleep disease Diseases 0.000 claims abstract description 7
- 230000008733 trauma Effects 0.000 claims abstract description 7
- 206010000117 Abnormal behaviour Diseases 0.000 claims abstract description 6
- 206010020772 Hypertension Diseases 0.000 claims abstract description 6
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 230000004064 dysfunction Effects 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 206010027175 memory impairment Diseases 0.000 claims abstract description 6
- 230000003340 mental effect Effects 0.000 claims abstract description 6
- 230000004899 motility Effects 0.000 claims abstract description 6
- 230000004770 neurodegeneration Effects 0.000 claims abstract description 6
- 208000022821 personality disease Diseases 0.000 claims abstract description 6
- 208000020016 psychiatric disease Diseases 0.000 claims abstract description 6
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- 210000003169 central nervous system Anatomy 0.000 claims abstract description 4
- 208000023516 stroke disease Diseases 0.000 claims abstract description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 30
- -1 amino compound Chemical class 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 14
- 229910021529 ammonia Inorganic materials 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 5
- 239000013543 active substance Substances 0.000 claims description 4
- 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 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 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
- 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
- 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 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
- 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
- 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
- YVJOCSNROXMPCD-UHFFFAOYSA-N 2-(4-chloro-5-fluoro-3-methoxyindol-1-yl)ethanamine Chemical compound C1=C(F)C(Cl)=C2C(OC)=CN(CCN)C2=C1 YVJOCSNROXMPCD-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
- LYEMDBHRTLIDHR-UHFFFAOYSA-N 2-(5-chloroindol-1-yl)ethanamine Chemical compound ClC1=CC=C2N(CCN)C=CC2=C1 LYEMDBHRTLIDHR-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
- 239000011737 fluorine Substances 0.000 claims description 2
- 210000000653 nervous system Anatomy 0.000 claims 3
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 239000012876 carrier material Substances 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 150000002475 indoles Chemical class 0.000 abstract description 9
- 229940054051 antipsychotic indole derivative Drugs 0.000 abstract description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 365
- 239000000243 solution Substances 0.000 description 299
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 293
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 214
- 239000000203 mixture Substances 0.000 description 168
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 125
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 123
- 239000002904 solvent Substances 0.000 description 113
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 112
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 112
- 239000012074 organic phase Substances 0.000 description 108
- 229910052938 sodium sulfate Inorganic materials 0.000 description 107
- 235000011152 sodium sulphate Nutrition 0.000 description 107
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 94
- 239000013078 crystal Substances 0.000 description 94
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 86
- 239000011541 reaction mixture Substances 0.000 description 78
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 76
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 75
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 73
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 73
- 239000000741 silica gel Substances 0.000 description 72
- 229910002027 silica gel Inorganic materials 0.000 description 72
- 239000008346 aqueous phase Substances 0.000 description 71
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 60
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 58
- 239000000725 suspension Substances 0.000 description 58
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 56
- 239000003921 oil Substances 0.000 description 55
- 235000019198 oils Nutrition 0.000 description 55
- 239000001530 fumaric acid Substances 0.000 description 38
- 239000002585 base Substances 0.000 description 37
- 235000002639 sodium chloride Nutrition 0.000 description 32
- 239000006185 dispersion Substances 0.000 description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- 150000002500 ions Chemical class 0.000 description 30
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 29
- 239000003054 catalyst Substances 0.000 description 29
- 229910000029 sodium carbonate Inorganic materials 0.000 description 29
- 239000012312 sodium hydride Substances 0.000 description 29
- 229910000104 sodium hydride Inorganic materials 0.000 description 29
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 22
- 239000011734 sodium Substances 0.000 description 20
- 229910052708 sodium Inorganic materials 0.000 description 19
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 18
- 239000012298 atmosphere Substances 0.000 description 18
- 238000001816 cooling Methods 0.000 description 18
- 239000012071 phase Substances 0.000 description 18
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 16
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 16
- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 16
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 16
- 229910003446 platinum oxide Inorganic materials 0.000 description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
- 235000011167 hydrochloric acid Nutrition 0.000 description 15
- 229960000443 hydrochloric acid Drugs 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000011780 sodium chloride Substances 0.000 description 14
- 229960002668 sodium chloride Drugs 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- GOOHAUXETOMSMM-GSVOUGTGSA-N R-propylene oxide Chemical compound C[C@@H]1CO1 GOOHAUXETOMSMM-GSVOUGTGSA-N 0.000 description 12
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 8
- 239000002775 capsule Substances 0.000 description 8
- 229940093499 ethyl acetate Drugs 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 239000000969 carrier Substances 0.000 description 7
- 239000012954 diazonium Substances 0.000 description 7
- 150000001989 diazonium salts Chemical class 0.000 description 7
- 229910021653 sulphate ion Inorganic materials 0.000 description 7
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-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
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 6
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- ODFFPRGJZRXNHZ-UHFFFAOYSA-N 5-fluoroindole Chemical compound FC1=CC=C2NC=CC2=C1 ODFFPRGJZRXNHZ-UHFFFAOYSA-N 0.000 description 5
- 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 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 239000001828 Gelatine Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 150000001540 azides Chemical class 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 229920000159 gelatin Polymers 0.000 description 5
- 235000019322 gelatine Nutrition 0.000 description 5
- 150000004678 hydrides Chemical class 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 238000000159 protein binding assay Methods 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 150000003385 sodium Chemical class 0.000 description 5
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- MYTGFBZJLDLWQG-UHFFFAOYSA-N 5-chloro-1h-indole Chemical compound ClC1=CC=C2NC=CC2=C1 MYTGFBZJLDLWQG-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 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
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000001117 sulphuric acid Substances 0.000 description 4
- 235000011149 sulphuric acid Nutrition 0.000 description 4
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 4
- IECRNNVUKPWFKJ-UHFFFAOYSA-N 1-(5-chloro-2-methylindol-1-yl)propan-2-ol Chemical compound ClC1=CC=C2N(CC(O)C)C(C)=CC2=C1 IECRNNVUKPWFKJ-UHFFFAOYSA-N 0.000 description 3
- YCVSNMPGFSFANR-UHFFFAOYSA-N 5,6-difluoro-1h-indole Chemical compound C1=C(F)C(F)=CC2=C1NC=C2 YCVSNMPGFSFANR-UHFFFAOYSA-N 0.000 description 3
- 102000006902 5-HT2C Serotonin Receptor Human genes 0.000 description 3
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- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
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- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([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
- 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
- 229910052987 metal hydride Inorganic materials 0.000 description 1
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- WZHJKEUHNJHDLS-QTGUNEKASA-N metergoline Chemical compound C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4N(C)C=C(C=34)C2)C1)C)NC(=O)OCC1=CC=CC=C1 WZHJKEUHNJHDLS-QTGUNEKASA-N 0.000 description 1
- 229960004650 metergoline Drugs 0.000 description 1
- ZMKCHSMRBSMDEX-UHFFFAOYSA-N methyl 2-azido-3-(3-chloro-4-fluorophenyl)prop-2-enoate Chemical compound COC(=O)C(N=[N+]=[N-])=CC1=CC=C(F)C(Cl)=C1 ZMKCHSMRBSMDEX-UHFFFAOYSA-N 0.000 description 1
- RXYCUKSOYJWGPE-UHFFFAOYSA-N methyl 2-azidoacetate Chemical compound COC(=O)CN=[N+]=[N-] RXYCUKSOYJWGPE-UHFFFAOYSA-N 0.000 description 1
- BSCVUXIUVIUPCJ-UHFFFAOYSA-N methyl 5-chloro-6-fluoro-1h-indole-2-carboxylate Chemical compound ClC1=C(F)C=C2NC(C(=O)OC)=CC2=C1 BSCVUXIUVIUPCJ-UHFFFAOYSA-N 0.000 description 1
- RNEYRDIYQLBSMW-UHFFFAOYSA-N methyl 7-chloro-6-fluoro-1h-indole-2-carboxylate Chemical compound C1=C(F)C(Cl)=C2NC(C(=O)OC)=CC2=C1 RNEYRDIYQLBSMW-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
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- 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
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- 239000002245 particle Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 238000003408 phase transfer catalysis Methods 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229960004838 phosphoric acid Drugs 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 102220013474 rs219779 Human genes 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 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
- 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
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
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- 238000012546 transfer Methods 0.000 description 1
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Classifications
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- 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
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- 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
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- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/20—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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Materials For Medical Uses (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Organic Insulating Materials (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH3201/93 | 1993-01-22 | ||
| CH320193 | 1993-10-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2132883A1 true CA2132883A1 (en) | 1995-04-23 |
Family
ID=4250849
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002132883A Abandoned CA2132883A1 (en) | 1993-10-22 | 1994-09-21 | 1-amino-ethylindole-derivatives |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US5494928A (OSRAM) |
| EP (1) | EP0655440A3 (OSRAM) |
| JP (1) | JP2638752B2 (OSRAM) |
| KR (1) | KR950011406A (OSRAM) |
| CN (1) | CN1061341C (OSRAM) |
| AU (1) | AU685841B2 (OSRAM) |
| BR (1) | BR9404203A (OSRAM) |
| CA (1) | CA2132883A1 (OSRAM) |
| CO (1) | CO4290356A1 (OSRAM) |
| CZ (1) | CZ260494A3 (OSRAM) |
| FI (1) | FI944969A7 (OSRAM) |
| HU (1) | HU218669B (OSRAM) |
| IL (1) | IL111314A (OSRAM) |
| NO (1) | NO301369B1 (OSRAM) |
| NZ (1) | NZ264713A (OSRAM) |
| PL (1) | PL179561B1 (OSRAM) |
| RU (1) | RU2136662C1 (OSRAM) |
| TW (1) | TW270114B (OSRAM) |
| ZA (1) | ZA948094B (OSRAM) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9523999D0 (en) | 1995-11-23 | 1996-01-24 | Lilly Co Eli | Indolyl neuropeptide y receptor antagonists |
| WO1997009308A1 (en) * | 1995-09-01 | 1997-03-13 | Eli Lilly And Company | Indolyl neuropeptide y receptor antagonists |
| WO1997047598A1 (en) * | 1996-06-12 | 1997-12-18 | 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 |
| KR100572900B1 (ko) * | 1997-08-07 | 2006-04-24 | 후지모토 쿄다이 가부시키가이샤 | 에틸아민 유도체 |
| US6960579B1 (en) | 1998-05-19 | 2005-11-01 | Alcon Manufacturing, Ltd. | Serotonergic 5HT7 receptor compounds for treating ocular and CNS disorders |
| CZ300647B6 (cs) * | 1998-08-21 | 2009-07-08 | Novartis Ag | Pevný farmaceutický prípravek pro perorální podávání obsahující tegaserod nebo jeho farmaceuticky prijatelnou sul |
| GB9819019D0 (en) | 1998-09-01 | 1998-10-28 | Cerebrus Ltd | Chemical compounds II |
| GB9819033D0 (en) * | 1998-09-01 | 1998-10-28 | Cerebrus Ltd | Chemical compounds VI |
| GB9819032D0 (en) * | 1998-09-01 | 1998-10-28 | Cerebrus Ltd | Chemical compounds IV |
| US6326379B1 (en) | 1998-09-16 | 2001-12-04 | Bristol-Myers Squibb Co. | Fused pyridine inhibitors of cGMP phosphodiesterase |
| AU755119B2 (en) | 1998-09-18 | 2002-12-05 | Alcon Laboratories, Inc. | Serotonergic 5HT2 agonists for treating glaucoma |
| 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 |
| WO2001032130A2 (en) * | 1999-11-05 | 2001-05-10 | Emisphere Technologies, Inc. | Phenyl amine 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 |
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| US7005443B1 (en) * | 2000-03-17 | 2006-02-28 | Alcon, Inc. | 5-Hydroxy indazole derivatives for treating glaucoma |
| US6956036B1 (en) | 2000-03-17 | 2005-10-18 | Alcon, Inc. | 6-hydroxy-indazole derivatives for treating glaucoma |
| WO2001070223A1 (en) * | 2000-03-17 | 2001-09-27 | Alcon, Inc. | Compounds with 5-ht2 and 5-ht1a agonist activity for treating glaucoma |
| US6806285B1 (en) | 2000-03-17 | 2004-10-19 | Alcon, Inc. | 5-Hydroxyl indole derivatives for treating glaucoma |
| WO2001070705A1 (en) | 2000-03-17 | 2001-09-27 | Alcon, Inc. | 2-acylaminobenzimidazole derivatives for treating glaucoma |
| ATE317846T1 (de) * | 2000-03-31 | 2006-03-15 | Purdue Research Foundation | Phosphoramidat-prodrugs |
| TWI290136B (en) | 2000-04-05 | 2007-11-21 | Daiichi Seiyaku Co | Ethylenediamine derivatives |
| AU5256301A (en) * | 2000-04-28 | 2001-11-12 | Yamanouchi Pharmaceutical Co., Ltd. | Froindazole derivative |
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| ATE433962T1 (de) | 2000-11-20 | 2009-07-15 | Biovitrum Ab Publ | Piperazinylpyrazinverbindungen als antagonisten des serotonin-5-ht2-rezeptors |
| SE0004245D0 (sv) | 2000-11-20 | 2000-11-20 | Pharmacia Ab | Novel compounds and their use |
| WO2004098807A1 (en) * | 2000-11-21 | 2004-11-18 | Barsplice Products, Inc. | Method of making steel couplers for joining concrete reinforcing bars |
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| CA2440438C (en) | 2001-03-09 | 2011-05-03 | Ortho-Mcneil Pharmaceutical, Inc. | Heterocyclic compounds |
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| BE791899A (fr) * | 1971-11-26 | 1973-05-24 | Ciba Geigy | Procede de preparation d'indoles n-substitues |
| US3904617A (en) * | 1972-10-12 | 1975-09-09 | Ayerst Mckenna & Harrison | Process for preparing new heterocyclic derivatives |
| IE37234B1 (en) * | 1972-02-14 | 1977-06-08 | Ayerst Mckenna & Harrison | Fused-ring indole derivatives |
| DE2430682A1 (de) * | 1974-06-26 | 1976-01-15 | Bayer Ag | Indolyl-mono-azofarbstoffe |
| FR2355006A1 (fr) * | 1976-06-17 | 1978-01-13 | Labaz | Nouveaux derives d'indole et procedes pour les preparer |
| DE2824447A1 (de) * | 1978-06-03 | 1979-12-13 | Cassella Ag | Pyrazino-carbazole, verfahren zu ihrer herstellung und sie enthaltendes pharmazeutisches mittel |
| DE3022648A1 (de) * | 1979-06-29 | 1981-01-15 | Sandoz Ag | Neue organische verbindungen, ihre herstellung und pharmazeutischen praeparate, welche diese verbindungen enthalten |
| FR2564465B1 (fr) * | 1984-05-16 | 1986-10-03 | Cortial | Nouveaux diamino-1,3 propanols-2, leurs methodes de preparation et leurs applications therapeutiques |
| PH23498A (en) * | 1984-08-06 | 1989-08-16 | Sterling Drug Inc | 3-carbonyl-1-aminoalkyl-1h-indoles,composition and use thereof |
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| CZ280738B6 (cs) * | 1988-02-10 | 1996-04-17 | F. Hoffmann - La Roche And Co., Aktiengesellschaft | Substituované pyrroly, jejich použití pro výrobu léčiv a léčiva na jejich bázi |
| FR2679561A1 (fr) * | 1991-07-26 | 1993-01-29 | Schneider Marc | Nouveaux derives de l'(indolyl-1) alkylamine substituee par une chaine presentant des groupements carbonyles conjugues a un noyau aromatique. |
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| EP0572863A1 (de) * | 1992-06-05 | 1993-12-08 | F. Hoffmann-La Roche Ag | ZNS Pyrazinoindole |
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-
1994
- 1994-09-07 TW TW083108265A patent/TW270114B/zh active
- 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 NZ NZ264713A patent/NZ264713A/en unknown
- 1994-10-17 IL IL11131494A patent/IL111314A/xx not_active IP Right Cessation
- 1994-10-17 HU HU9402983A patent/HU218669B/hu not_active IP Right Cessation
- 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 NO NO943999A patent/NO301369B1/no not_active IP Right Cessation
- 1994-10-21 PL PL94305543A patent/PL179561B1/pl unknown
- 1994-10-21 CZ CZ942604A patent/CZ260494A3/cs unknown
- 1994-10-21 BR BR9404203A patent/BR9404203A/pt not_active Application Discontinuation
- 1994-10-21 FI FI944969A patent/FI944969A7/fi 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 |
|---|---|
| NZ264713A (en) | 1996-05-28 |
| EP0655440A2 (de) | 1995-05-31 |
| NO301369B1 (no) | 1997-10-20 |
| CZ260494A3 (en) | 1995-10-18 |
| JPH07149723A (ja) | 1995-06-13 |
| IL111314A0 (en) | 1994-12-29 |
| EP0655440A3 (de) | 1996-11-06 |
| HU9402983D0 (en) | 1995-02-28 |
| PL179561B1 (pl) | 2000-09-29 |
| CO4290356A1 (es) | 1996-04-17 |
| KR950011406A (ko) | 1995-05-15 |
| AU685841B2 (en) | 1998-01-29 |
| CN1105988A (zh) | 1995-08-02 |
| RU94037964A (ru) | 1996-09-10 |
| RU2136662C1 (ru) | 1999-09-10 |
| AU7583794A (en) | 1995-05-11 |
| NO943999L (no) | 1995-04-24 |
| FI944969A7 (fi) | 1995-04-23 |
| FI944969A0 (fi) | 1994-10-21 |
| IL111314A (en) | 1999-08-17 |
| JP2638752B2 (ja) | 1997-08-06 |
| US5494928A (en) | 1996-02-27 |
| HUT70848A (en) | 1995-11-28 |
| PL305543A1 (en) | 1995-05-02 |
| HU218669B (hu) | 2000-10-28 |
| NO943999D0 (no) | 1994-10-21 |
| BR9404203A (pt) | 1995-07-04 |
| TW270114B (OSRAM) | 1996-02-11 |
| CN1061341C (zh) | 2001-01-31 |
| ZA948094B (en) | 1995-04-24 |
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| FZDE | Discontinued |