DE3348331C2 - - Google Patents
Info
- Publication number
- DE3348331C2 DE3348331C2 DE3348331A DE3348331A DE3348331C2 DE 3348331 C2 DE3348331 C2 DE 3348331C2 DE 3348331 A DE3348331 A DE 3348331A DE 3348331 A DE3348331 A DE 3348331A DE 3348331 C2 DE3348331 C2 DE 3348331C2
- Authority
- DE
- Germany
- Prior art keywords
- serotonin
- compounds
- formula
- acid
- addition salts
- 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.)
- Expired - Lifetime
Links
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 53
- 229940076279 serotonin Drugs 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000002464 receptor antagonist Substances 0.000 claims description 7
- 229940044551 receptor antagonist Drugs 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- DYVWOGCIQANCRE-UHFFFAOYSA-N 5-fluoro-1-methylindole-3-carboxylic acid Chemical compound FC1=CC=C2N(C)C=C(C(O)=O)C2=C1 DYVWOGCIQANCRE-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 description 15
- 238000000034 method Methods 0.000 description 13
- 238000012360 testing method Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 208000002193 Pain Diseases 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 230000036982 action potential Effects 0.000 description 5
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229960002748 norepinephrine Drugs 0.000 description 4
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 210000001170 unmyelinated nerve fiber Anatomy 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 230000008485 antagonism Effects 0.000 description 3
- 230000003288 anthiarrhythmic effect Effects 0.000 description 3
- 239000003416 antiarrhythmic agent Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- ROGHUJUFCRFUSO-UHFFFAOYSA-N 1h-indole-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1C=CN2 ROGHUJUFCRFUSO-UHFFFAOYSA-N 0.000 description 2
- GYSCXPVAKHVAAY-UHFFFAOYSA-N 3-Nonanol Chemical compound CCCCCCC(O)CC GYSCXPVAKHVAAY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 208000019695 Migraine disease Diseases 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical class ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 230000002763 arrhythmic effect Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000002860 competitive effect Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 210000005036 nerve Anatomy 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000005936 piperidyl group Chemical group 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 210000001186 vagus nerve Anatomy 0.000 description 2
- KPJZHOPZRAFDTN-ZRGWGRIASA-N (6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)CC)C2)=C3C2=CN(C)C3=C1 KPJZHOPZRAFDTN-ZRGWGRIASA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- VKRAXSZEDRWLAG-SJKOYZFVSA-N 2-bromo-lsd Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N(CC)CC)C2)=C3C2=C(Br)NC3=C1 VKRAXSZEDRWLAG-SJKOYZFVSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 238000006820 Bouveault-Blanc reduction reaction Methods 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000006561 Cluster Headache Diseases 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
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 102000006386 Myelin Proteins Human genes 0.000 description 1
- 108010083674 Myelin Proteins Proteins 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 206010042434 Sudden death Diseases 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
- IOYNQIMAUDJVEI-BMVIKAAMSA-N Tepraloxydim Chemical group C1C(=O)C(C(=N/OC\C=C\Cl)/CC)=C(O)CC1C1CCOCC1 IOYNQIMAUDJVEI-BMVIKAAMSA-N 0.000 description 1
- XQJMXPAEFMWDOZ-PBWFPOADSA-N [(1s,5r)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] benzoate Chemical compound C([C@H]1CC[C@@H](C2)N1C)C2OC(=O)C1=CC=CC=C1 XQJMXPAEFMWDOZ-PBWFPOADSA-N 0.000 description 1
- RNIPBGMVTAUWNH-UHFFFAOYSA-N [F].[I] Chemical compound [F].[I] RNIPBGMVTAUWNH-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000002460 anti-migrenic effect Effects 0.000 description 1
- 229940082988 antihypertensives serotonin antagonists Drugs 0.000 description 1
- 239000000164 antipsychotic agent Substances 0.000 description 1
- 229940005529 antipsychotics Drugs 0.000 description 1
- 239000003420 antiserotonin agent Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- -1 bicyclic heterocyclic carboxylic acids Chemical class 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- DHZBEENLJMYSHQ-XCVPVQRUSA-N cantharidin Chemical compound C([C@@H]1O2)C[C@@H]2[C@]2(C)[C@@]1(C)C(=O)OC2=O DHZBEENLJMYSHQ-XCVPVQRUSA-N 0.000 description 1
- 229940095758 cantharidin Drugs 0.000 description 1
- 229930008397 cantharidin Natural products 0.000 description 1
- DHZBEENLJMYSHQ-UHFFFAOYSA-N cantharidine Natural products O1C2CCC1C1(C)C2(C)C(=O)OC1=O DHZBEENLJMYSHQ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 208000018912 cluster headache syndrome Diseases 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000013265 extended release Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 210000000245 forearm Anatomy 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002496 iodine Chemical class 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
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229960001186 methysergide Drugs 0.000 description 1
- TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 description 1
- 229960004503 metoclopramide Drugs 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 210000005012 myelin Anatomy 0.000 description 1
- 210000004126 nerve fiber Anatomy 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- 206010033675 panniculitis Diseases 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 210000004304 subcutaneous tissue Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 206010044652 trigeminal neuralgia Diseases 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
-
- 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
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
- C07D451/12—Oxygen atoms acylated by aromatic or heteroaromatic carboxylic acids, e.g. cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/14—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing 9-azabicyclo [3.3.1] nonane ring systems, e.g. granatane, 2-aza-adamantane; Cyclic acetals thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH397982 | 1982-06-29 | ||
CH426782 | 1982-07-13 | ||
CH695082 | 1982-11-30 | ||
CH695182 | 1982-11-30 | ||
CH749582 | 1982-12-22 | ||
CH749482 | 1982-12-22 | ||
CH125683 | 1983-03-09 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE3348331C2 true DE3348331C2 (en, 2012) | 1992-08-06 |
Family
ID=27561049
Family Applications (6)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE3348334A Expired - Lifetime DE3348334C2 (en, 2012) | 1982-06-29 | 1983-06-23 | |
DE3348331A Expired - Lifetime DE3348331C2 (en, 2012) | 1982-06-29 | 1983-06-23 | |
DE3348332A Expired - Lifetime DE3348332C2 (en, 2012) | 1982-06-29 | 1983-06-23 | |
DE3348333A Expired - Lifetime DE3348333C2 (en, 2012) | 1982-06-29 | 1983-06-23 | |
DE1994175004 Active DE19475004I2 (de) | 1982-06-29 | 1983-06-23 | Indolylcarbonsaeuretropyl- und- chinuclidinylester |
DE19833322574 Granted DE3322574A1 (de) | 1982-06-29 | 1983-06-23 | Benzoesaeurepiperidylester-derivate bzw. verfahren zu deren herstellung und deren verwendung |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE3348334A Expired - Lifetime DE3348334C2 (en, 2012) | 1982-06-29 | 1983-06-23 |
Family Applications After (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE3348332A Expired - Lifetime DE3348332C2 (en, 2012) | 1982-06-29 | 1983-06-23 | |
DE3348333A Expired - Lifetime DE3348333C2 (en, 2012) | 1982-06-29 | 1983-06-23 | |
DE1994175004 Active DE19475004I2 (de) | 1982-06-29 | 1983-06-23 | Indolylcarbonsaeuretropyl- und- chinuclidinylester |
DE19833322574 Granted DE3322574A1 (de) | 1982-06-29 | 1983-06-23 | Benzoesaeurepiperidylester-derivate bzw. verfahren zu deren herstellung und deren verwendung |
Country Status (20)
Country | Link |
---|---|
US (3) | US4803199A (en, 2012) |
AT (1) | AT391136B (en, 2012) |
AU (2) | AU570002B2 (en, 2012) |
CH (2) | CH669792A5 (en, 2012) |
CY (1) | CY1500A (en, 2012) |
DE (6) | DE3348334C2 (en, 2012) |
DK (1) | DK172475B1 (en, 2012) |
FI (1) | FI74707C (en, 2012) |
FR (1) | FR2531083B1 (en, 2012) |
GB (4) | GB2125398B (en, 2012) |
HK (1) | HK60690A (en, 2012) |
HU (1) | HU191053B (en, 2012) |
IL (1) | IL69081A (en, 2012) |
IT (1) | IT1173724B (en, 2012) |
NL (2) | NL191991C (en, 2012) |
NZ (1) | NZ204714A (en, 2012) |
PT (1) | PT76937B (en, 2012) |
SE (1) | SE463210B (en, 2012) |
SG (1) | SG53789G (en, 2012) |
WO (1) | WO1984000166A1 (en, 2012) |
Families Citing this family (142)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FI74707C (fi) * | 1982-06-29 | 1988-03-10 | Sandoz Ag | Foerfarande foer framstaellning av terapeutiskt anvaendbara alkylenoeverbryggade piperidylestrar eller -amider av bicykliska karboxylsyror. |
JPS5936675A (ja) * | 1982-07-13 | 1984-02-28 | サンド・アクチエンゲゼルシヤフト | 二環性複素環式カルボン酸アザビシクロアルキルエステルまたはアミド |
EP0135545A1 (en) * | 1983-02-19 | 1985-04-03 | Beecham Group Plc | Azabicycloalkyl benzamide and anilide derivatives |
GB8315495D0 (en) * | 1983-06-06 | 1983-07-13 | Sumitomo Chemical Co | Fungicidal aniline derivatives |
DE3429830A1 (de) * | 1983-08-26 | 1985-03-07 | Sandoz-Patent-GmbH, 7850 Lörrach | Automatische carbonsaeure- und sulfonsaeureester oder -amide |
JPS6084281A (ja) * | 1983-09-14 | 1985-05-13 | Yoshitomi Pharmaceut Ind Ltd | 3−インド−ルカルボキサミド類 |
US4888353A (en) * | 1986-02-28 | 1989-12-19 | Erbamont, Inc. | Carboxamides useful as antiemetic or antipsychotic agents |
US5175173A (en) * | 1983-12-22 | 1992-12-29 | Sun Jung Hui | Carboxamides useful as antiemetic or antipsychotic agents |
DE3445377A1 (de) * | 1983-12-23 | 1985-07-04 | Sandoz-Patent-GmbH, 7850 Lörrach | Carbocylische und heterocyclische carbonsaeureester und -amide von ueberbrueckten und nicht ueberbrueckten cyclischen stickstoffhaltigen aminen oder alkoholen |
US4593034A (en) * | 1984-04-06 | 1986-06-03 | A. H. Robins Company, Inc. | 2-alkoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamides and thiobenzamides |
ATE86110T1 (de) * | 1984-12-20 | 1993-03-15 | Sandoz Ag | Behandlung von gastrointestinalkrankheiten durch anwendung von 5-ht3-antagonisten. |
CH667657A5 (de) * | 1985-01-07 | 1988-10-31 | Sandoz Ag | Carbocyclische und heterocyclische carbonylmethylen- und methylpiperidine und -pyrrolidine. |
US4605652A (en) * | 1985-02-04 | 1986-08-12 | A. H. Robins Company, Inc. | Method of enhancing memory or correcting memory deficiency with arylamido (and arylthioamido)-azabicycloalkanes |
DE385517T1 (de) * | 1985-03-14 | 1991-07-25 | Beecham Group p.l.c., Brentford, Middlesex | Arzneimittel zur behandlung von erbrechen. |
US4937247A (en) * | 1985-04-27 | 1990-06-26 | Beecham Group P.L.C. | 1-acyl indazoles |
DE3687080T2 (de) * | 1985-04-27 | 1993-03-25 | Beecham Group Plc | Azabicyclononyl-indazol-carboxamid mit 5-ht-antagonistischer wirkung. |
GB8623142D0 (en) * | 1986-09-26 | 1986-10-29 | Beecham Group Plc | Compounds |
GB8525913D0 (en) * | 1985-10-21 | 1985-11-27 | Beecham Group Plc | Compounds |
GB8511988D0 (en) * | 1985-05-11 | 1985-06-19 | Beecham Group Plc | Compounds |
GB8515845D0 (en) * | 1985-06-22 | 1985-07-24 | Beecham Group Plc | Treatment |
GB8518658D0 (en) * | 1985-07-24 | 1985-08-29 | Glaxo Group Ltd | Medicaments |
US5204356A (en) * | 1985-07-24 | 1993-04-20 | Glaxo Group Limited | Treatment of anxiety |
GB8520616D0 (en) * | 1985-08-16 | 1985-09-25 | Beecham Group Plc | Compounds |
GB8525844D0 (en) * | 1985-10-19 | 1985-11-20 | Beecham Group Plc | Compounds |
DE3687980T2 (de) * | 1986-01-07 | 1993-06-17 | Beecham Group Plc | Indolderivate mit einer azabicyclischen seitenkette, verfahren zu ihrer herstellung, zwischenprodukte und pharmazeutische zusammensetzungen. |
EP0235878A3 (en) * | 1986-01-16 | 1989-06-14 | Beecham Group Plc | Novel compounds |
US4722834A (en) * | 1986-03-05 | 1988-02-02 | A. H. Robins Company, Incorporated | Method of using 2-alkoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide-N-oxides to control emesis caused by anticancer drugs |
US4717563A (en) * | 1986-03-05 | 1988-01-05 | A. H. Robins Company, Inc. | 2-alkoxy-N-(1-azabicyclo(2.2.2)oct-3-yl) benzamides and thiobenzamides in a method for alleviating emesis caused by non-platinum anticancer drugs |
EP0254584B1 (en) * | 1986-07-25 | 1992-10-07 | Beecham Group Plc | Azabicyclic compounds, process for their preparation, and their pharmaceutical use |
HU895334D0 (en) * | 1986-07-30 | 1990-01-28 | Sandoz Ag | Process for the preparation of nasal pharmaceutical compositions |
EP0255297B1 (en) * | 1986-07-31 | 1993-04-21 | Beecham Group Plc | Azabicyclic compounds, process for their preparation, and their pharmaceutical use |
AT396870B (de) * | 1986-08-07 | 1993-12-27 | Sandoz Ag | Verfahren zur herstellung einer galenischen formulierung zur nasalen verabreichung von serotoninantagonisten |
US4772459A (en) * | 1986-09-09 | 1988-09-20 | Erbamont, Inc. | Method for controlling emesis caused by chemotherapeutic agents and antiemetic agents useful therein |
ES2094718T3 (es) * | 1986-09-22 | 1997-02-01 | Janssen Pharmaceutica Nv | Antagonistas de la serotonine para el tratamiento de heridas. |
US4906755A (en) * | 1986-11-03 | 1990-03-06 | Merrell Dow Pharmaceuticals Inc. | Esters of hexahydro-8-hydroxy-2,6-methano-2H-quinolizin-3-(4H)-one and related compounds |
ZA878096B (en) * | 1986-11-03 | 1988-04-26 | Merrell Dow Pharmaceuticals Inc. | Esters of hexahydro-8-hydroxy-2,6-methano-2h-quinolizin-3(4h)-one and related compounds |
ES2036587T5 (es) * | 1986-11-21 | 1995-10-16 | Glaxo Group Ltd | Medicamentos para el tratamiento o prevencion del sindrome de abstinencia. |
US5198447A (en) * | 1986-11-21 | 1993-03-30 | Glaxo Group Limited | Medicaments |
DE3780276T2 (de) * | 1986-12-16 | 1993-02-25 | Robins Co Inc A H | Angstloesende n-(1-azabicyclo(2.2.2)oct-3-yl)benzamide und -thiobenzamide. |
DK662687A (da) * | 1986-12-17 | 1988-06-18 | Glaxo Group Ltd | Anvendelse af tricycliske carbazoloner |
US5246941A (en) * | 1986-12-17 | 1993-09-21 | Glaxo Group Limited | Method for the treatment of depression |
US5190954A (en) * | 1986-12-17 | 1993-03-02 | Glaxo Group Limited | Methods for the treatment of cognitive disorders |
EP0278173B1 (en) * | 1986-12-17 | 1993-11-03 | Glaxo Group Limited | Use of heterocyclic derivatives in the treatment of depressions |
US5200414A (en) * | 1986-12-17 | 1993-04-06 | Glaxo Group Limited | Methods for the treatment of cognitive disorders |
EP0279990B1 (en) * | 1986-12-17 | 1995-07-12 | Glaxo Group Limited | Use of heterocyclic derivatives in the treatment of cognitive disorders |
US5244909A (en) * | 1986-12-17 | 1993-09-14 | Glaxo Group Limited | Methods for the treatment of cognitive disorders |
GB8806990D0 (en) * | 1988-03-23 | 1988-04-27 | Beecham Group Plc | Novel compounds |
GB8701022D0 (en) * | 1987-01-19 | 1987-02-18 | Beecham Group Plc | Treatment |
EP0287196B1 (en) * | 1987-02-18 | 1994-11-23 | Beecham Group Plc | Indole derivatives, process for their preparation and pharmaceutical compositions containing them |
DE3881950T2 (de) * | 1987-04-25 | 1993-09-30 | Beecham Group Plc | Azabicyclische Verbindungen, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen. |
FR2616149B1 (fr) * | 1987-06-04 | 1990-10-19 | Adir | Nouveau derive de l'acide benzo (b) thiophene - 7 carboxylique, son procede de preparation et les compositions pharmaceutiques qui le contiennent |
DE3822792C2 (de) * | 1987-07-11 | 1997-11-27 | Sandoz Ag | Neue Verwendung von 5HT¶3¶-Antagonisten |
GB8718445D0 (en) * | 1987-08-04 | 1987-09-09 | Wyeth John & Brother Ltd | Pyridyl-ethers |
CA1307790C (en) * | 1987-08-04 | 1992-09-22 | Ian Anthony Cliffe | Ethers |
DE3827253A1 (de) * | 1987-08-20 | 1989-03-02 | Sandoz Ag | Ester und amide von cyclischen carbonsaeuren und cyclischen alkoholen und aminen sowie verfahren zu deren herstellung und sie enthaltende therapeutische zusammensetzungen |
GB8720805D0 (en) * | 1987-09-04 | 1987-10-14 | Naylor R J | 2-alkoxy-n-(1-azabicyclo(2 2 2)oct-3-yl)benzamides & thiobenzamides |
US4921982A (en) * | 1988-07-21 | 1990-05-01 | Eli Lilly And Company | 5-halo-2,3-dihydro-2,2-dimethylbenzofuran-7-carboxylic acids useful as intermediates for 5-HT3 antagonists |
US5364863A (en) * | 1987-09-08 | 1994-11-15 | Eli Lilly And Company | Specific 5-HT3 antagonists |
GB8723157D0 (en) * | 1987-10-02 | 1987-11-04 | Beecham Group Plc | Compounds |
EP0311724A1 (en) * | 1987-10-16 | 1989-04-19 | Synthelabo | Anxiolytic-R-N-(1-azabicyclo[2.2.2]oct-3-yl) benzamides and thiobenzamides |
CA1304082C (en) * | 1987-10-22 | 1992-06-23 | Tetsuya Tahara | Benzoxazine compounds and pharmaceutical use thereof |
DK680788A (da) * | 1987-12-10 | 1989-06-11 | Duphar Int Res | Indolcarboxylsyreestere og -amider, deres fremstilling of laegemidler indeholdende forbindelserne |
US4863919A (en) * | 1988-02-01 | 1989-09-05 | A. H. Robins Company, Incorporated | Method of enhancing memory or correcting memory deficiency with arylamido(and arylthiomido)-azabicycloalkanes |
ES2080727T3 (es) * | 1988-02-23 | 1996-02-16 | Merrell Pharma Inc | Uso de quinolizina y derivados de quinolizinona en la fabricacion de medicamentos. |
IT1226389B (it) * | 1988-07-12 | 1991-01-15 | Angeli Inst Spa | Nuovi derivati ammidinici e guanidinici |
US5166341A (en) * | 1988-07-29 | 1992-11-24 | Dainippon Pharmaceutical Co., Ltd. | 6-amino-1,4-hexahydro-1H-diazepine derivatives |
US5017573A (en) * | 1988-07-29 | 1991-05-21 | Dainippon Pharmaceutical Co., Ltd. | Indazole-3-carboxylic acid derivatives |
DE3878235T2 (de) * | 1988-08-04 | 1993-06-03 | Synthelabo | Antischizophren-wirksame s-n-(1-azabicyclo (2.2.2.)oct-3-yl)benzamide und thiobenzamide. |
CA2004911A1 (en) * | 1988-12-22 | 1990-06-22 | Mitsuaki Ohta | 4,5,6,7-tetrahydrobenzimidazole derivatives |
AU626980B2 (en) * | 1989-02-02 | 1992-08-13 | Astellas Pharma Inc. | Tetrahydrobenzimidazole derivatives |
GB8904551D0 (en) * | 1989-02-28 | 1989-04-12 | Glaxo Group Ltd | Chemical compounds |
US4914207A (en) * | 1989-05-09 | 1990-04-03 | Pfizer Inc. | Arylthiazolylimidazoles |
GB8913646D0 (en) * | 1989-06-14 | 1989-08-02 | Glaxo Group Ltd | Chemical compounds |
US5126343A (en) * | 1989-09-11 | 1992-06-30 | G. D. Searle & Co. | N-azabicyclo [3.3.0]octane amides of aromatic acids |
US5225419A (en) * | 1989-10-14 | 1993-07-06 | John Wyeth & Brother, Limited | Certain 1,8-ethano or propano-1,4-dihydro-4-oxo-quinoline-3-carboxamides and derivatives thereof |
GB2236751B (en) | 1989-10-14 | 1993-04-28 | Wyeth John & Brother Ltd | Heterocyclic compounds |
CA2030051C (en) * | 1989-11-17 | 2001-08-07 | Haruhiko Kikuchi | Indole derivatives |
US5446050A (en) * | 1989-11-17 | 1995-08-29 | Pfizer Inc. | Azabicyclo amides and esters as 5-HT3 receptor antagonists |
GB8928837D0 (en) * | 1989-12-21 | 1990-02-28 | Beecham Group Plc | Pharmaceuticals |
GB9009542D0 (en) * | 1990-04-27 | 1990-06-20 | Beecham Group Plc | Novel compounds |
US5223613A (en) * | 1990-04-27 | 1993-06-29 | G. D. Searle & Co. | Azatetracycle compounds and process of preparing same |
US5140023A (en) * | 1990-04-27 | 1992-08-18 | G. D. Searle & Co. | Azatetracycle compounds |
US5187166A (en) * | 1990-07-31 | 1993-02-16 | Nisshin Flour Milling Co., Ltd. | Azabicyclo derivatives and their use as antiemetics |
US5189041A (en) * | 1990-11-16 | 1993-02-23 | Syntex (U.S.A.) Inc. | Tricyclic 5-ht3 receptor antagonists |
WO1992009284A1 (en) * | 1990-11-29 | 1992-06-11 | Rhone-Poulenc Rorer International (Holdings), Inc. | 2,6-methano-2h-1-benzoxocincarboxamides as 5-ht3-antagonists |
JP3026845B2 (ja) * | 1991-02-20 | 2000-03-27 | 日清製粉株式会社 | ピペリジン誘導体 |
US5227377A (en) * | 1991-03-07 | 1993-07-13 | G. D. Searle & Co. | Meso-azacyclic amides of certain bicyclic carboxylic acids |
US5196547A (en) * | 1991-03-07 | 1993-03-23 | G. D. Searle & Co. | Meso-azacyclic amides of imidazopyridine carboxylic acids and analogs thereof |
EP0528026A1 (en) * | 1991-03-07 | 1993-02-24 | G.D. Searle & Co. | New meso-azacyclic aromatic acid amides and esters as novel serotonergic agents |
US5234921A (en) * | 1991-03-07 | 1993-08-10 | G. D. Searle & Co. | Meso-azacyclic amides of imidazopyridine carboxylic acids and analogs thereof as pharmaceuticals |
US5137893A (en) * | 1991-03-07 | 1992-08-11 | G. D. Searle & Co. | Pharmaceutically useful meso-azacyclic amides of imidazopyridine carboxylic acids and analogs thereof |
US5516782A (en) * | 1991-03-07 | 1996-05-14 | G. D. Searle & Co. | New meso-azacyclic aromatic acid amides and esters as novel serotonergic agents |
US5260303A (en) * | 1991-03-07 | 1993-11-09 | G. D. Searle & Co. | Imidazopyridines as serotonergic 5-HT3 antagonists |
US5219850A (en) * | 1991-03-07 | 1993-06-15 | G. D. Searle & Co. | Pharmaceutically useful meso-azacyclic amides of imidazopyridine carboxylic acids and analogs thereof |
PT100785A (pt) * | 1991-08-20 | 1994-04-29 | Smithkline Beecham Plc | Utilizacao de compostos, por exemplo indole-3-carboxilatos, para a producao de medicamentos, compostos ai utilizados e composicoes farmaceuticas que os contem. |
US5552398A (en) * | 1991-09-12 | 1996-09-03 | Smithkline Beecham P.L.C. | Azabicyclic compounds as 5-HT4 receptor antagonists |
US5344831A (en) * | 1992-01-31 | 1994-09-06 | Nisshin Flour Milling Co., Ltd. | Diazabicyclo derivatives |
JPH05310732A (ja) * | 1992-03-12 | 1993-11-22 | Mitsubishi Kasei Corp | シンノリン−3−カルボン酸誘導体 |
US5852014A (en) * | 1992-03-12 | 1998-12-22 | Smithkline Beecham P.L.C. | Condensed indole derivatives as 5HT4 -receptor antagonists |
JP2699794B2 (ja) * | 1992-03-12 | 1998-01-19 | 三菱化学株式会社 | チエノ〔3,2−b〕ピリジン誘導体 |
US5236931A (en) * | 1992-03-26 | 1993-08-17 | A. H. Robins Company, Incorporated | 2-substituted benzamide and benzoate derivatives of 3-aminoquinuclidine and 3-quinuclidinol |
US5748825A (en) * | 1992-08-03 | 1998-05-05 | Rockwell, Iii; Marshall A. | Liquid crystal optical waveguide display system |
GR1001378B (el) * | 1992-10-08 | 1993-10-29 | Smithkline Beecham Plc | Ανταγωνιστές 5-ΗΤ4 πιπεριδυλαλκυλίου. |
ES2056728B1 (es) * | 1992-10-28 | 1995-05-01 | Smithkline Beecham Plc | Nuevos derivados de piperidilo y aminoalquilo con actividad antagonista del receptor 5-ht4 |
GB9414900D0 (en) * | 1994-07-23 | 1994-09-14 | Smithkline Beecham Plc | Novel process |
US5723103A (en) * | 1994-12-09 | 1998-03-03 | Vanderbilt University | Substituted benzamides and radioligand analogs and methods of use |
WO2000044743A1 (fr) * | 1999-01-28 | 2000-08-03 | Nippon Shinyaku Co., Ltd. | Derives d'amides et compositions de medicaments |
KR20010112673A (ko) * | 2000-06-09 | 2001-12-21 | 김환기 | 트로피세트론 염산염(일반식ⅰ)의 제조방법 |
US6486172B2 (en) | 2000-08-18 | 2002-11-26 | Pharmacia & Upjohn Company | Quinuclidine-substituted aryl compounds for treatment of disease |
US6492385B2 (en) | 2000-08-18 | 2002-12-10 | Pharmacia & Upjohn Company | Quinuclidine-substituted heteroaryl moieties for treatment of disease |
WO2002016358A2 (en) | 2000-08-18 | 2002-02-28 | Pharmacia & Upjohn Company | Quinuclidine-substituted aryl moieties for treatment of disease (nicotinic acetylcholine receptor ligands) |
AU2001282875A1 (en) | 2000-08-21 | 2002-03-04 | Pharmacia And Upjohn Company | Quinuclidine-substituted heteroaryl moieties for treatment of disease |
WO2002015662A2 (en) | 2000-08-21 | 2002-02-28 | Pharmacia & Upjohn Company | Quinuclidine-substituted heteroaryl moieties for treatment of disease (nicotinic acetylcholine receptor antagonists |
AR036040A1 (es) | 2001-06-12 | 2004-08-04 | Upjohn Co | Compuestos de heteroarilo multiciclicos sustituidos con quinuclidinas y composiciones farmaceuticas que los contienen |
AR036041A1 (es) * | 2001-06-12 | 2004-08-04 | Upjohn Co | Compuestos aromaticos heterociclicos sustituidos con quinuclidina y composiciones farmaceuticas que los contienen |
AUPR701101A0 (en) * | 2001-08-14 | 2001-09-06 | Commonwealth Scientific And Industrial Research Organisation | Agonists and antagonists of 5ht3-like receptors of invertebrates as pesticides |
BR0212123A (pt) * | 2001-08-24 | 2004-07-20 | Upjohn Co | 7-aza[2.2.1]biciclo-heptanos substituìdos com arila para o tratamento de doenças |
WO2003022856A1 (en) * | 2001-09-12 | 2003-03-20 | Pharmacia & Upjohn Company | Substituted 7-aza[2.2.1] bicycloheptanes for the treatment of diseases |
ES2383001T3 (es) | 2001-10-02 | 2012-06-15 | Pharmacia & Upjohn Company Llc | Compuestos de heteroarilo condensado sustituidos con azabicíclico para el tratamiento de enfermedades |
US6849620B2 (en) | 2001-10-26 | 2005-02-01 | Pfizer Inc | N-(azabicyclo moieties)-substituted hetero-bicyclic aromatic compounds for the treatment of disease |
ES2307902T3 (es) * | 2002-02-12 | 2008-12-01 | N.V. Organon | Derivados de indolina e indol 1-arilsulfonil-3- sustituidos utilizados en el tratamiento de transtornos del sistema nervioso central. |
JP2005522456A (ja) | 2002-02-15 | 2005-07-28 | ファルマシア・アンド・アップジョン・カンパニー・エルエルシー | Cns関連障害治療のためのアザビシクロ置換ベンゾイルアミドおよびチオアミド |
EP1476449A1 (en) * | 2002-02-19 | 2004-11-17 | PHARMACIA & UPJOHN COMPANY | Fused bicyclic-n-bridged-heteroaromatic carboxamides for the treatment of disease |
WO2003070731A2 (en) * | 2002-02-19 | 2003-08-28 | Pharmacia & Upjohn Company | Azabicyclic compounds for the treatment of disease |
US7001900B2 (en) * | 2002-02-20 | 2006-02-21 | Pfizer Inc. | Azabicyclic compounds for the treatment of disease |
EP1542999A1 (en) | 2002-08-01 | 2005-06-22 | Pharmacia & Upjohn Company LLC | 1h-pyrazole and 1h-pyrrole-azabicyclic compounds with alfa-7 nachr activity |
EP1543000B1 (en) | 2002-09-25 | 2013-03-06 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, and benzoisothiazoles, and preparation and uses thereof |
WO2004039815A2 (en) * | 2002-11-01 | 2004-05-13 | Pharmacia & Upjohn Company Llc | Compounds having both alpha7 nachr agonist and 5ht antagonist activity for treatment of cns diseases |
JP2006525364A (ja) | 2003-04-30 | 2006-11-09 | ジ インスチチュート フォー ファーマシューティカル ディスカバリー、エルエルシー | 置換アミノカルボン酸 |
JP4824578B2 (ja) | 2003-12-22 | 2011-11-30 | メモリー・ファーマシューティカルズ・コーポレイション | インドール類、1,2−ベンズイソオキサゾール類、および1,2−ベンゾイソチアゾール類、ならびにそれらの製造と使用 |
WO2005092890A2 (en) | 2004-03-25 | 2005-10-06 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, and preparation and uses thereof |
CA2567977A1 (en) * | 2004-04-22 | 2006-01-05 | Memory Pharmaceutical Corporation | Indoles, 1h-indazoles, 1,2-benzisoxazoles, 1,2-benzoisothiazoles, and preparation and uses thereof |
WO2005111038A2 (en) | 2004-05-07 | 2005-11-24 | Memory Pharmaceuticals Corporation | 1h-indazoles, benzothiazoles, 1,2-benzoisoxazoles, 1,2-benzoisothiazoles, and chromones and preparation and uses thereof |
CN100390172C (zh) * | 2004-09-10 | 2008-05-28 | 成都欣捷高新技术开发有限公司 | 一种甲磺酸多拉司琼晶型及其制备方法 |
WO2006055725A2 (en) | 2004-11-18 | 2006-05-26 | The Institutes For Pharmaceutical Discovery, Llc | Substituted amino acids as protein tyrosine phosphatase inhibitors |
JP2008525464A (ja) * | 2004-12-22 | 2008-07-17 | メモリー・ファーマシューティカルズ・コーポレイション | α−7ニコチン性受容体リガンド並びにその製造及び使用 |
US8106066B2 (en) | 2005-09-23 | 2012-01-31 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, pyrazolopyridines, isothiazolopyridines, and preparation and uses thereof |
HRP20180531T1 (hr) | 2009-05-20 | 2018-06-01 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Antagonisti serotoninskog 5-ht3 receptora za uporabu u liječenju površina vestibularnih lezija |
ES2432618T3 (es) | 2009-05-20 | 2013-12-04 | Inserm (Institut National De La Santé Et De La Recherche Medicale) | Antagonistas del receptor 5-HT3 de serotonina para usar en el tratamiento o prevención de una patología del oído interno con déficit vestibular |
JOP20130213B1 (ar) | 2012-07-17 | 2021-08-17 | Takeda Pharmaceuticals Co | معارضات لمستقبلht3-5 |
EP3201203B1 (en) | 2014-09-29 | 2021-05-19 | Takeda Pharmaceutical Company Limited | Crystalline form of 1-(1-methyl-1h-pyrazol-4-yl)-n-((1r,5s,7s)-9-methyl-3-oxa-9-azabicyclo[3.3.1]nonan-7-yl)-1h-indole-3-carboxamide |
RU2681931C2 (ru) * | 2017-08-01 | 2019-03-14 | Фарид Шамилевич Шагиахметов | Фармацевтическая комбинация для лечения алкогольной зависимости |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0067770A2 (en) * | 1981-06-13 | 1982-12-22 | Merrell Dow France Et Cie | Treatment of migraine with tropyl benzoate derivatives |
Family Cites Families (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3170927A (en) * | 1965-02-23 | O chzoh | ||
US2478134A (en) * | 1947-11-25 | 1949-08-02 | Samuel W Smith | Simulated bowling target |
GB774858A (en) * | 1954-10-20 | 1957-05-15 | Sandoz Ltd | Tropane and -Î-tropane derivatives and process for preparation thereof |
AT198771B (de) * | 1956-03-09 | 1958-07-25 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von neuen Estern und deren Salzen |
US3342826A (en) * | 1964-01-13 | 1967-09-19 | Ile De France | Heterocyclic aminoalkyl benzamides |
US3405134A (en) * | 1965-08-17 | 1968-10-08 | Colgate Palmolive Co | Quinuclidyl esters of aromatic acids |
SE331841B (en, 2012) * | 1967-05-23 | 1971-01-18 | Astra Ab | |
US3702324A (en) * | 1970-06-24 | 1972-11-07 | Stanford Research Inst | 3,4,5-trimethoxybenzamides of substituted anilines and of alkylpiperidines |
GB1293446A (en) * | 1970-07-23 | 1972-10-18 | Rech S Et D Applic Scient Soge | Quinuclidine derivatives, the preparation thereof and pharmaceutical compositions containing them |
CH614709A5 (en, 2012) * | 1975-09-25 | 1979-12-14 | Ciba Geigy Ag | |
NL7611713A (nl) * | 1975-11-03 | 1977-05-05 | Thomae Gmbh Dr K | Werkwijze voor de bereiding van verbindingen en preparaten met waardevolle farmacologische eigen- schappen. |
DE2548968A1 (de) * | 1975-11-03 | 1977-05-12 | Thomae Gmbh Dr K | Neue amino-benzoesaeureamide |
GB1593146A (en) * | 1976-11-05 | 1981-07-15 | Beecham Group Ltd | Octahydro-quinolizinyl benzamide derivatives |
IL59004A0 (en) * | 1978-12-30 | 1980-03-31 | Beecham Group Ltd | Substituted benzamides their preparation and pharmaceutical compositions containing them |
FR2476088A2 (fr) * | 1979-01-16 | 1981-08-21 | Delalande Sa | Nouveaux derives du nor-tropane, leur procede de preparation et leur application en therapeutique |
NZ197356A (en) * | 1980-06-18 | 1984-05-31 | Beecham Group Ltd | Ar-alkylsulphinyl-n-(azaicycloalkyl(alkyl)) benzamides |
FR2493848B2 (fr) * | 1980-11-07 | 1986-05-16 | Delalande Sa | Nouveaux derives des nor-tropane et granatane, leur procede de preparation et leur application en therapeutique |
FR2499570A1 (fr) * | 1981-02-11 | 1982-08-13 | Delalande Sa | Nouveaux derives du b-amino-3 nor-tropane et leur procede de preparation |
GB2100259B (en) * | 1981-06-13 | 1984-10-31 | Merrell Toraude & Co | Treatment of migraine with tropyl benzoate derivatives |
EP0067615B1 (en) * | 1981-06-17 | 1986-01-08 | Beecham Group Plc | Alkylthio derivatives of azabicyclobenzamides, their preparation and pharmaceutical compositions |
EP0069482A1 (en) * | 1981-06-29 | 1983-01-12 | Beecham Group Plc | Azabicycloalkyl benzamides, process for their preparation and pharmaceutical compositions containing them |
EP0068700A1 (en) * | 1981-06-29 | 1983-01-05 | Beecham Group Plc | Azobicycloalkylbenzamides, process for their preparation and pharmaceutical compositions containing them |
NZ200981A (en) * | 1981-07-17 | 1984-10-19 | Recordati Chem Pharm | 3-methylflavone-8-carboxylic acid derivatives and pharmaceutical compositions |
DE3275296D1 (en) * | 1981-10-01 | 1987-03-05 | Beecham Group Plc | Azabicyclo-(3,3,1)-nonylbenzamide derivatives, processes for their preparation, and pharmaceutical compositions containing them |
FI74707C (fi) * | 1982-06-29 | 1988-03-10 | Sandoz Ag | Foerfarande foer framstaellning av terapeutiskt anvaendbara alkylenoeverbryggade piperidylestrar eller -amider av bicykliska karboxylsyror. |
FR2529548A1 (fr) * | 1982-07-02 | 1984-01-06 | Delalande Sa | Nouveaux derives de l'amino-3 quinuclidine, leur procede et leur application en therapeutique |
ATE19881T1 (de) * | 1982-12-10 | 1986-06-15 | Merrell Toraude & Co | Tropyl- und pseudotropylalkylbenzoate und ihre verwendung in der behandlung von migraene. |
GB8302483D0 (en) * | 1983-01-29 | 1983-03-02 | Beecham Group Plc | Compounds |
EP0135545A1 (en) * | 1983-02-19 | 1985-04-03 | Beecham Group Plc | Azabicycloalkyl benzamide and anilide derivatives |
FR2546169B1 (fr) * | 1983-05-20 | 1986-03-21 | Delalande Sa | N-oxydes de derives aminocycliques, leur procede de preparation et leur application en therapeutique |
-
1983
- 1983-06-22 FI FI832293A patent/FI74707C/fi not_active IP Right Cessation
- 1983-06-22 FR FR8310433A patent/FR2531083B1/fr not_active Expired
- 1983-06-23 DE DE3348334A patent/DE3348334C2/de not_active Expired - Lifetime
- 1983-06-23 DE DE3348331A patent/DE3348331C2/de not_active Expired - Lifetime
- 1983-06-23 DE DE3348332A patent/DE3348332C2/de not_active Expired - Lifetime
- 1983-06-23 DE DE3348333A patent/DE3348333C2/de not_active Expired - Lifetime
- 1983-06-23 DE DE1994175004 patent/DE19475004I2/de active Active
- 1983-06-23 DE DE19833322574 patent/DE3322574A1/de active Granted
- 1983-06-24 WO PCT/CH1983/000081 patent/WO1984000166A1/de unknown
- 1983-06-24 NL NL8302253A patent/NL191991C/xx not_active IP Right Cessation
- 1983-06-27 SE SE8303651A patent/SE463210B/sv not_active IP Right Cessation
- 1983-06-27 AU AU16286/83A patent/AU570002B2/en not_active Expired
- 1983-06-27 IL IL69081A patent/IL69081A/xx not_active IP Right Cessation
- 1983-06-27 IT IT48580/83A patent/IT1173724B/it active Protection Beyond IP Right Term
- 1983-06-27 GB GB08317365A patent/GB2125398B/en not_active Expired
- 1983-06-27 PT PT76937A patent/PT76937B/pt unknown
- 1983-06-27 CY CY1500A patent/CY1500A/en unknown
- 1983-06-27 DK DK198302951A patent/DK172475B1/da not_active IP Right Cessation
- 1983-06-27 NZ NZ204714A patent/NZ204714A/xx unknown
- 1983-06-28 AT AT2358/83A patent/AT391136B/de not_active IP Right Cessation
- 1983-06-28 HU HU832335A patent/HU191053B/hu unknown
-
1984
- 1984-06-24 CH CH904/84A patent/CH669792A5/de not_active IP Right Cessation
-
1985
- 1985-08-12 GB GB08520186A patent/GB2166726B/en not_active Expired
- 1985-08-12 GB GB08520187A patent/GB2166727B/en not_active Expired
- 1985-08-12 GB GB08520188A patent/GB2166728B/en not_active Expired
-
1987
- 1987-11-25 US US07/125,048 patent/US4803199A/en not_active Expired - Lifetime
- 1987-12-10 AU AU82434/87A patent/AU603399B2/en not_active Expired
-
1988
- 1988-06-24 CH CH3305/88A patent/CH669954A5/de not_active IP Right Cessation
- 1988-11-15 US US07/272,030 patent/US4910207A/en not_active Expired - Lifetime
-
1989
- 1989-08-23 SG SG537/89A patent/SG53789G/en unknown
-
1990
- 1990-01-17 US US07/466,550 patent/US5017582A/en not_active Expired - Lifetime
- 1990-08-09 HK HK606/90A patent/HK60690A/xx not_active IP Right Cessation
-
1997
- 1997-06-02 NL NL970021C patent/NL970021I2/nl unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0067770A2 (en) * | 1981-06-13 | 1982-12-22 | Merrell Dow France Et Cie | Treatment of migraine with tropyl benzoate derivatives |
Non-Patent Citations (1)
Title |
---|
Chem.Abstr. 89, 1978, 167x * |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE3348331C2 (en, 2012) | ||
CH664567A5 (de) | Aromatische carbonsaeure- und sulfonsaeureester oder -amide. | |
WO1985002847A1 (fr) | Esters et amides d'acides carboniques carbocycliques et heterocycliques d'amines ou d'alcools azotes cycliques portes et non portes | |
Clarke et al. | Compounds affecting the central nervous system. 4. 3. beta.-phenyltropane-2-carboxylic esters and analogs | |
CH667657A5 (de) | Carbocyclische und heterocyclische carbonylmethylen- und methylpiperidine und -pyrrolidine. | |
DE69332095T2 (de) | Thieno(3,2-b)Pyridinderivate zur Behandlung von Magen-Darmstörungen | |
DE69009195T2 (de) | Isoxazol-Derivate mit Anti-Serotonin-Aktivität, deren Herstellungsverfahren und diese enthaltende Zusammensetzungen. | |
DE3750359T2 (de) | Ester des Hexahydro-8-hydroxy-2,6-methano-2H-chinolizin-3(4H)-ons und verwandte Verbindungen. | |
DE3810552A1 (de) | Ester und amide von indol-, benzo(b)thiopen-, benzo(b)furancarbonsaeuren oder 4-amino-2-methoxy-benzolsaeuren mit n-heterocyclischen oder n-heterobicyclischen alkoholen oder aminen, verfahren zu deren herstellung sie enthaltende pharmazeutische zusammensetzungen sowie applikator zur verabreichung derselben | |
DD235638A5 (de) | Neue neuromuskulaere blockierungsmittel | |
DE69112594T2 (de) | Dihydrobenzofurancarboxamide und Verfahren zu ihrer Herstellung. | |
DE3500251C2 (de) | Neue 8alpha-Acylaminoergoline | |
DE69918046T2 (de) | Neue basische Derivate von Benz(e)isoindol-1-onen und Pyrrolo(3,4-c)chinolin-1-onen mit 5-HT3-antagonistischer Aktivität, ihre Herstellung und ihre therapeutische Verwendung | |
DE2347142A1 (de) | Chemisches verfahren | |
DE68905363T2 (de) | Heterotetracyclische laktamderivate, verfahren zu ihrer herstellung und pharmazeutische zubereitungen, die sie enthalten. | |
EP0665014B1 (de) | 3-Benzoyl-3,7-diazabicyclo(3,3,1)nonan-Verbindungen mit anti-arrhythmischer Wirkung | |
DE69006675T2 (de) | Aroylharnstoffe. | |
DD209628A5 (de) | Verfahren zur herstellung von imidazolinderivaten | |
CH653032A5 (de) | Bicyclische verbindungen, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel. | |
EP1270576B1 (de) | 3-Phenyl-3,7-diazabicyclo(3,3,1)nonan-Verbindungen sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
DE2935685C2 (de) | 2-Brom-9,10-dihydroergosin und seine Säureadditonssalze, Verfahren zu deren Herstellung sowie diese Verbindung enthaltende Arzneimittel | |
DE60119336T2 (de) | Verwendungen von thaliporphin oder seinen derivaten in der behandlung von herzkrankheiten und seine herstellung | |
DE2002107A1 (de) | Neue organische Verbindungen und Verfahren zu deren Herstellung | |
AT337161B (de) | Verfahren zur herstellung von neuen 3-phenoxy-3-phenylpropylaminen und deren saureadditionssalzen | |
DE1543673C3 (de) | Basisch substituierte Benzofuranderivate und deren pharmazeutisch verträgliche Säureadditionssalze sowie Verfahren zu deren Herstellung und Arzneimittel mit einem Gehalt dieser Verbindungen |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
Q172 | Divided out of (supplement): |
Ref country code: DE Ref document number: 3322574 |
|
8181 | Inventor (new situation) |
Free format text: DONATSCH, PETER, DR., ALLSCHWEIL, CH ENGEL, GUENTER, DR., 7858 WEIL, DE HUEGI, BRUNO, DR., PFEFFINGEN, CH RICHARDSON, BRIAN PETER, DR., MAGDEN, CH STADLER, PAUL, DR., BIEL-BENKEN, CH |
|
8110 | Request for examination paragraph 44 | ||
AC | Divided out of |
Ref country code: DE Ref document number: 3322574 Format of ref document f/p: P |
|
AC | Divided out of |
Ref country code: DE Ref document number: 3322574 Format of ref document f/p: P |
|
D2 | Grant after examination | ||
8364 | No opposition during term of opposition | ||
8327 | Change in the person/name/address of the patent owner |
Owner name: NOVARTIS AG, BASEL, CH |
|
8328 | Change in the person/name/address of the agent |
Free format text: SPOTT WEINMILLER & PARTNER, 80336 MUENCHEN |