DE3807533C2 - - Google Patents
Info
- Publication number
- DE3807533C2 DE3807533C2 DE3807533A DE3807533A DE3807533C2 DE 3807533 C2 DE3807533 C2 DE 3807533C2 DE 3807533 A DE3807533 A DE 3807533A DE 3807533 A DE3807533 A DE 3807533A DE 3807533 C2 DE3807533 C2 DE 3807533C2
- Authority
- DE
- Germany
- Prior art keywords
- compound
- general formula
- compounds
- pharmaceutically acceptable
- formula
- 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 - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 claims description 84
- 150000003839 salts Chemical class 0.000 claims description 15
- -1 methoxy, hydroxy, acetamino, acetyl Chemical group 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 3
- 150000002475 indoles Chemical class 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 239000008177 pharmaceutical agent Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000000126 substance Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 238000005984 hydrogenation reaction Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 230000036772 blood pressure Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QXJMCSBBTMVSJS-UHFFFAOYSA-N 1-(1h-indol-2-yl)ethanone Chemical class C1=CC=C2NC(C(=O)C)=CC2=C1 QXJMCSBBTMVSJS-UHFFFAOYSA-N 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003245 coal Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- MRBDMNSDAVCSSF-UHFFFAOYSA-N phentolamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 MRBDMNSDAVCSSF-UHFFFAOYSA-N 0.000 description 3
- 229960001999 phentolamine Drugs 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 2
- HUUPVABNAQUEJW-UHFFFAOYSA-N 1-methylpiperidin-4-one Chemical compound CN1CCC(=O)CC1 HUUPVABNAQUEJW-UHFFFAOYSA-N 0.000 description 2
- XCOJBYZDWMZKAF-UHFFFAOYSA-N 7,13-diazatetracyclo[9.7.0.03,8.012,16]octadeca-1,3(8),4,6,9,11,13,15,17-nonaene Chemical class N1=CC=C2C=CC=3C(=C12)C=CC1=C(C=3)C=CC=N1 XCOJBYZDWMZKAF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000004480 active ingredient Substances 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000017858 demethylation Effects 0.000 description 2
- 238000010520 demethylation reaction Methods 0.000 description 2
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- INYCZGVYPRTSPR-UHFFFAOYSA-N l007596 Chemical compound C1C2CN(C)CCC2CC(=O)C2=C1C1=CC=CC=C1N2 INYCZGVYPRTSPR-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 208000031225 myocardial ischemia Diseases 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 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
- 238000012546 transfer Methods 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- HBBCKARIXVLLRZ-UHFFFAOYSA-N 1-(1h-indol-2-yl)-n,n-dimethylmethanamine Chemical compound C1=CC=C2NC(CN(C)C)=CC2=C1 HBBCKARIXVLLRZ-UHFFFAOYSA-N 0.000 description 1
- NJVXSQAOKMJYGN-UHFFFAOYSA-N 10-methoxy-5-methyl-5,12-diazatetracyclo[9.7.0.03,8.013,18]octadeca-1(11),13,15,17-tetraene Chemical compound COC1CC2CCN(C)CC2CC2=C1NC1=CC=CC=C21 NJVXSQAOKMJYGN-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
- FQTFHMSZCSUVEU-UHFFFAOYSA-N 4-(2-amino-1-hydroxyethyl)benzene-1,2-diol;hydron;chloride Chemical compound Cl.NCC(O)C1=CC=C(O)C(O)=C1 FQTFHMSZCSUVEU-UHFFFAOYSA-N 0.000 description 1
- CNBGESOKDJESED-UHFFFAOYSA-N 5-methyl-5,12-diazatetracyclo[9.7.0.03,8.013,18]octadeca-1(11),3(8),13,15,17-pentaen-10-one Chemical compound C1N(C)CCC(CC2=O)=C1CC1=C2NC2=CC=CC=C12 CNBGESOKDJESED-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005541 ACE inhibitor Substances 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- METLQVFFFUYXNT-QTPGKHNVSA-N Ervatamine Chemical compound O=C1C[C@H]2[C@H](CC)CN(C)C[C@@]2(C(=O)OC)CC2=C1NC1=CC=CC=C21 METLQVFFFUYXNT-QTPGKHNVSA-N 0.000 description 1
- METLQVFFFUYXNT-UHFFFAOYSA-N Ervatamine Natural products O=C1CC2C(CC)CN(C)CC2(C(=O)OC)CC2=C1NC1=CC=CC=C21 METLQVFFFUYXNT-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 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 1
- 239000001358 L(+)-tartaric acid Substances 0.000 description 1
- 235000011002 L(+)-tartaric acid Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
- 229910019020 PtO2 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000000219 Sympatholytic Substances 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 102000004305 alpha Adrenergic Receptors Human genes 0.000 description 1
- 108090000861 alpha Adrenergic Receptors Proteins 0.000 description 1
- 102000015007 alpha-adrenergic receptor activity proteins Human genes 0.000 description 1
- 108040006816 alpha-adrenergic receptor activity proteins Proteins 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- 239000013011 aqueous formulation Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 208000006218 bradycardia Diseases 0.000 description 1
- 230000036471 bradycardia 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
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000001713 cholinergic effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
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- 238000007796 conventional method Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
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- 239000002552 dosage form Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000742 histaminergic effect Effects 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- JBXRLVPILRXPNH-UHFFFAOYSA-N indol-6-one Chemical compound O=C1C=CC2=CC=NC2=C1 JBXRLVPILRXPNH-UHFFFAOYSA-N 0.000 description 1
- 229930005303 indole alkaloid Natural products 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 208000012866 low blood pressure Diseases 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000003760 magnetic stirring Methods 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
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 229960001289 prazosin Drugs 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 229960003598 promazine Drugs 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000011158 quantitative evaluation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- CGRKYEALWSRNJS-UHFFFAOYSA-N sodium;2-methylbutan-2-olate Chemical compound [Na+].CCC(C)(C)[O-] CGRKYEALWSRNJS-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000009154 spontaneous behavior Effects 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000000948 sympatholitic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- 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
- C07D471/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (30)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3807533A DE3807533A1 (de) | 1988-03-08 | 1988-03-08 | Pyridocycloheptindol-verbindungen, verfahren zu ihrer herstellung und pharmazeutische mittel, die diese verbindungen enthalten |
| LU87463A LU87463A1 (fr) | 1988-03-08 | 1989-03-01 | Composes de derives d'indole,procede pour leur preparation et medicaments qui contiennent ces composes |
| SE8900725A SE500580C2 (sv) | 1988-03-08 | 1989-03-02 | Indolföreningar och förfaranden för framställning därav |
| AT0047389A AT395243B (de) | 1988-03-08 | 1989-03-02 | Indolderivate, ein verfahren zu ihrer herstellung und pharmazeutische mittel, die diese verbindungen enthalten |
| GB8904792A GB2216889B (en) | 1988-03-08 | 1989-03-02 | Indole compounds and a process for their preparation |
| CH807/89A CH677792A5 (en, 2012) | 1988-03-08 | 1989-03-02 | |
| IE70089A IE61683B1 (en) | 1988-03-08 | 1989-03-03 | Indole compounds and a process for their preparation |
| IL8947689A IL89476A (en) | 1988-03-08 | 1989-03-03 | 2h-pyrido [3',4':4,5] cyclohept [1,2-b] indol- 6-ol and 6-one derivatives, their preparation and pharmaceutical compositions containing them |
| IT8919648A IT1228569B (it) | 1988-03-08 | 1989-03-03 | Derivati dell'indolo, procedimento per la loro preparazione e mezzi farmaceutici contenenti tali composti. |
| NZ228246A NZ228246A (en) | 1988-03-08 | 1989-03-07 | Pyridocylohept-indolones and their pharmaceutical compositions |
| YU00484/89A YU48489A (en) | 1988-03-08 | 1989-03-07 | Indole derivatives and process for preparing thereof |
| NO89890978A NO890978L (no) | 1988-03-08 | 1989-03-07 | Fremgangsmaate ved fremstilling av indolforbindelser. |
| AU31095/89A AU610701B2 (en) | 1988-03-08 | 1989-03-07 | Indole compounds, a process for their preparation and pharmaceutical compositions containing these compounds |
| FR8902978A FR2628426A1 (fr) | 1988-03-08 | 1989-03-07 | Derives d'indole, procede pour leur preparation et medicaments qui contiennent ces composes |
| HU891112A HU205355B (en) | 1988-03-08 | 1989-03-07 | Process for producing indole derivatives and pharmaceutical compositions comprising same |
| CN89102030A CN1024551C (zh) | 1988-03-08 | 1989-03-07 | 吲哚衍生物的制备方法 |
| DK110089A DK110089A (da) | 1988-03-08 | 1989-03-07 | Indolderivater, fremgangsmaade til deres fremstilling og farmaceutiske praeparater, som indeholder disse forbindelser |
| SU894613697A SU1650012A3 (ru) | 1988-03-08 | 1989-03-07 | Способ получени производных индола или их гидрохлоридов, или тартратов |
| NL8900552A NL8900552A (nl) | 1988-03-08 | 1989-03-07 | Indoolderivaten, werkwijze voor hun bereiding en farmaceutische preparaten die deze verbindingen bevatten. |
| ZA891721A ZA891721B (en) | 1988-03-08 | 1989-03-07 | Indole compounds and a process for their preparation |
| KR1019890002754A KR910004449B1 (ko) | 1988-03-08 | 1989-03-07 | 인돌 화합물, 이들의 제조방법 및 이들 화합물을 함유하는 약학적 조성물 |
| GR890100145A GR1000311B (el) | 1988-03-08 | 1989-03-07 | Μεθοδος παρασκευης ενωσεων ινδολης. |
| DD89326336A DD283622A5 (de) | 1988-03-08 | 1989-03-07 | Verfahren zur herstellung von indolderivaten |
| CS891437A CZ143789A3 (en) | 1988-03-08 | 1989-03-07 | DERIVATIVES OF PYRIDO £3', 4':4,5|CYCLOHEPT£1,2-b|INDOLE, THEIR PHARMACEUTICALLY ACCEPTABLE SALTS, PHARMACEUTICAL PREPARATIONS IN WHICH SAID COMPOUNDS ARE COMPRISED AND PROCESS FOR PREPARING THEREOF |
| FI891086A FI92066C (fi) | 1988-03-08 | 1989-03-08 | Menetelmä valmistaa farmakologisesti arvokkaita pyrido/3',4';4,5/syklohept/1,2-b/indolijohdannaisia |
| JP1053974A JPH0613514B2 (ja) | 1988-03-08 | 1989-03-08 | インドール化合物、その製造方法および該化合物を含有する血圧降下および徐脈作用を有する心臓循環疾患の治療剤 |
| PL1989278135A PL159893B1 (en) | 1988-03-08 | 1989-03-08 | The production method of indole derivatives |
| PT89941A PT89941B (pt) | 1988-03-08 | 1989-03-08 | Processo para a preparacao de derivados de indol, de composicoes farmaceuticas que os contem e de produtos intermediarios |
| BE8900249A BE1002923A4 (fr) | 1988-03-08 | 1989-03-08 | Derives d'indole, procede pour leur preparation et medicaments qui contiennent ces composes. |
| US07/629,188 US5159080A (en) | 1988-03-08 | 1990-12-18 | Indole compounds, a process for their preparation, and pharmaceutical compositions containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3807533A DE3807533A1 (de) | 1988-03-08 | 1988-03-08 | Pyridocycloheptindol-verbindungen, verfahren zu ihrer herstellung und pharmazeutische mittel, die diese verbindungen enthalten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3807533A1 DE3807533A1 (de) | 1989-09-21 |
| DE3807533C2 true DE3807533C2 (en, 2012) | 1993-08-26 |
Family
ID=6349134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3807533A Granted DE3807533A1 (de) | 1988-03-08 | 1988-03-08 | Pyridocycloheptindol-verbindungen, verfahren zu ihrer herstellung und pharmazeutische mittel, die diese verbindungen enthalten |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US5159080A (en, 2012) |
| JP (1) | JPH0613514B2 (en, 2012) |
| KR (1) | KR910004449B1 (en, 2012) |
| CN (1) | CN1024551C (en, 2012) |
| AT (1) | AT395243B (en, 2012) |
| AU (1) | AU610701B2 (en, 2012) |
| BE (1) | BE1002923A4 (en, 2012) |
| CH (1) | CH677792A5 (en, 2012) |
| CZ (1) | CZ143789A3 (en, 2012) |
| DD (1) | DD283622A5 (en, 2012) |
| DE (1) | DE3807533A1 (en, 2012) |
| DK (1) | DK110089A (en, 2012) |
| FI (1) | FI92066C (en, 2012) |
| FR (1) | FR2628426A1 (en, 2012) |
| GB (1) | GB2216889B (en, 2012) |
| GR (1) | GR1000311B (en, 2012) |
| HU (1) | HU205355B (en, 2012) |
| IE (1) | IE61683B1 (en, 2012) |
| IL (1) | IL89476A (en, 2012) |
| IT (1) | IT1228569B (en, 2012) |
| LU (1) | LU87463A1 (en, 2012) |
| NL (1) | NL8900552A (en, 2012) |
| NO (1) | NO890978L (en, 2012) |
| NZ (1) | NZ228246A (en, 2012) |
| PL (1) | PL159893B1 (en, 2012) |
| PT (1) | PT89941B (en, 2012) |
| SE (1) | SE500580C2 (en, 2012) |
| SU (1) | SU1650012A3 (en, 2012) |
| YU (1) | YU48489A (en, 2012) |
| ZA (1) | ZA891721B (en, 2012) |
-
1988
- 1988-03-08 DE DE3807533A patent/DE3807533A1/de active Granted
-
1989
- 1989-03-01 LU LU87463A patent/LU87463A1/fr unknown
- 1989-03-02 AT AT0047389A patent/AT395243B/de not_active IP Right Cessation
- 1989-03-02 CH CH807/89A patent/CH677792A5/de not_active IP Right Cessation
- 1989-03-02 SE SE8900725A patent/SE500580C2/sv unknown
- 1989-03-02 GB GB8904792A patent/GB2216889B/en not_active Expired - Fee Related
- 1989-03-03 IT IT8919648A patent/IT1228569B/it active
- 1989-03-03 IE IE70089A patent/IE61683B1/en not_active IP Right Cessation
- 1989-03-03 IL IL8947689A patent/IL89476A/en unknown
- 1989-03-07 GR GR890100145A patent/GR1000311B/el unknown
- 1989-03-07 DD DD89326336A patent/DD283622A5/de not_active IP Right Cessation
- 1989-03-07 ZA ZA891721A patent/ZA891721B/xx unknown
- 1989-03-07 DK DK110089A patent/DK110089A/da not_active Application Discontinuation
- 1989-03-07 YU YU00484/89A patent/YU48489A/xx unknown
- 1989-03-07 AU AU31095/89A patent/AU610701B2/en not_active Ceased
- 1989-03-07 NO NO89890978A patent/NO890978L/no unknown
- 1989-03-07 SU SU894613697A patent/SU1650012A3/ru active
- 1989-03-07 CZ CS891437A patent/CZ143789A3/cs unknown
- 1989-03-07 HU HU891112A patent/HU205355B/hu not_active IP Right Cessation
- 1989-03-07 CN CN89102030A patent/CN1024551C/zh not_active Expired - Fee Related
- 1989-03-07 FR FR8902978A patent/FR2628426A1/fr active Granted
- 1989-03-07 NL NL8900552A patent/NL8900552A/nl not_active Application Discontinuation
- 1989-03-07 NZ NZ228246A patent/NZ228246A/en unknown
- 1989-03-07 KR KR1019890002754A patent/KR910004449B1/ko not_active Expired
- 1989-03-08 PT PT89941A patent/PT89941B/pt not_active IP Right Cessation
- 1989-03-08 PL PL1989278135A patent/PL159893B1/pl unknown
- 1989-03-08 JP JP1053974A patent/JPH0613514B2/ja not_active Expired - Lifetime
- 1989-03-08 BE BE8900249A patent/BE1002923A4/fr not_active IP Right Cessation
- 1989-03-08 FI FI891086A patent/FI92066C/fi not_active IP Right Cessation
-
1990
- 1990-12-18 US US07/629,188 patent/US5159080A/en not_active Expired - Fee Related
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| OP8 | Request for examination as to paragraph 44 patent law | ||
| 8127 | New person/name/address of the applicant |
Owner name: MADAUS AG, 5000 KOELN, DE |
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| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |