SE446736B - Beta-karbolin-3-karboxylsyraderivat och framstellning derav - Google Patents
Beta-karbolin-3-karboxylsyraderivat och framstellning deravInfo
- Publication number
- SE446736B SE446736B SE8107493A SE8107493A SE446736B SE 446736 B SE446736 B SE 446736B SE 8107493 A SE8107493 A SE 8107493A SE 8107493 A SE8107493 A SE 8107493A SE 446736 B SE446736 B SE 446736B
- Authority
- SE
- Sweden
- Prior art keywords
- carbon atoms
- compound
- alkyl
- carboxylic acid
- carboline
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 13
- ARLVFKCLBYUINL-UHFFFAOYSA-N 9h-pyrido[3,4-b]indole-3-carboxylic acid Chemical class N1C2=CC=CC=C2C2=C1C=NC(C(=O)O)=C2 ARLVFKCLBYUINL-UHFFFAOYSA-N 0.000 title claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 56
- 150000001875 compounds Chemical class 0.000 claims abstract description 53
- 238000000034 method Methods 0.000 claims abstract description 23
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- 125000001424 substituent group Chemical group 0.000 claims abstract description 7
- -1 amino compound Chemical class 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229910052794 bromium Inorganic materials 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 239000000460 chlorine Substances 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 16
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 10
- 125000006239 protecting group Chemical group 0.000 claims description 9
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 229910004013 NO 2 Inorganic materials 0.000 claims description 6
- 150000001350 alkyl halides Chemical class 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 150000002828 nitro derivatives Chemical class 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 230000026030 halogenation Effects 0.000 claims description 3
- 238000005658 halogenation reaction Methods 0.000 claims description 3
- 150000002475 indoles Chemical class 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 abstract description 2
- AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical class N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 114
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- 239000000203 mixture Substances 0.000 description 43
- 239000000243 solution Substances 0.000 description 39
- 150000002168 ethanoic acid esters Chemical class 0.000 description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 238000002844 melting Methods 0.000 description 30
- 230000008018 melting Effects 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 239000000741 silica gel Substances 0.000 description 22
- 229910002027 silica gel Inorganic materials 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 238000001816 cooling Methods 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000499 gel Substances 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 12
- 238000002425 crystallisation Methods 0.000 description 12
- 230000008025 crystallization Effects 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000012362 glacial acetic acid Substances 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 6
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 6
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 230000007717 exclusion Effects 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 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 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 229930040373 Paraformaldehyde Natural products 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
- MOQOOKGPCBQMCY-UHFFFAOYSA-N acetic acid;hexane Chemical compound CC(O)=O.CCCCCC MOQOOKGPCBQMCY-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 239000000010 aprotic solvent Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- IUHKSTINHDUYRO-UHFFFAOYSA-N ethyl 4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=CC=C2C3=C(COC)C(C(=O)OCC)=NC=C3NC2=C1 IUHKSTINHDUYRO-UHFFFAOYSA-N 0.000 description 4
- XZFNJRASXSVQBZ-UHFFFAOYSA-N ethyl 6-amino-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound N1C2=CC=C(N)C=C2C2=C1C=NC(C(=O)OCC)=C2 XZFNJRASXSVQBZ-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- 229920002866 paraformaldehyde Polymers 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000006356 dehydrogenation reaction Methods 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- FMLHHZMITXIXJR-UHFFFAOYSA-N ethyl 6-amino-4-methyl-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C(N)C=C2C3=C(C)C(C(=O)OCC)=NC=C3NC2=C1 FMLHHZMITXIXJR-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 3
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 3
- 235000019799 monosodium phosphate Nutrition 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- YSEFYOVWKJXNCH-UHFFFAOYSA-N 2-methoxyacetaldehyde Chemical compound COCC=O YSEFYOVWKJXNCH-UHFFFAOYSA-N 0.000 description 2
- HQAXHIGPGBPPFU-UHFFFAOYSA-N 2-prop-2-ynoxyoxane Chemical compound C#CCOC1CCCCO1 HQAXHIGPGBPPFU-UHFFFAOYSA-N 0.000 description 2
- SICNEQNVWDROPT-UHFFFAOYSA-N 4-(methoxymethyl)-1-(4-methylphenyl)sulfonylindole Chemical compound C1=CC=2C(COC)=CC=CC=2N1S(=O)(=O)C1=CC=C(C)C=C1 SICNEQNVWDROPT-UHFFFAOYSA-N 0.000 description 2
- JPONOTGMJUOKCE-UHFFFAOYSA-N 4-(methoxymethyl)-1h-indole Chemical compound COCC1=CC=CC2=C1C=CN2 JPONOTGMJUOKCE-UHFFFAOYSA-N 0.000 description 2
- YIZNPYBICIOFLG-UHFFFAOYSA-N 9h-pyrido[3,4-b]indole-3-carboxamide Chemical class N1C2=CC=CC=C2C2=C1C=NC(C(=O)N)=C2 YIZNPYBICIOFLG-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
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- SADNNRATNFCDQC-UHFFFAOYSA-N ethyl 6,7-dimethoxy-4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound COC1=C(OC)C=C2C3=C(COC)C(C(=O)OCC)=NC=C3NC2=C1 SADNNRATNFCDQC-UHFFFAOYSA-N 0.000 description 1
- ZBVSSKCFFMRTKP-UHFFFAOYSA-N ethyl 6-(1,1-dioxo-1,2-thiazolidin-2-yl)-4-methyl-9H-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C2C3=C(C)C(C(=O)OCC)=NC=C3NC2=CC=C1N1CCCS1(=O)=O ZBVSSKCFFMRTKP-UHFFFAOYSA-N 0.000 description 1
- XIQBYBJEPTXQBU-UHFFFAOYSA-N ethyl 6-(3-chloropropylsulfonylamino)-4-methyl-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C(NS(=O)(=O)CCCCl)C=C2C3=C(C)C(C(=O)OCC)=NC=C3NC2=C1 XIQBYBJEPTXQBU-UHFFFAOYSA-N 0.000 description 1
- PUHKLTSNYMLMHH-UHFFFAOYSA-N ethyl 6-(3-diethoxyphosphorylprop-1-ynyl)-9H-pyrido[3,4-b]indole-3-carboxylate Chemical compound C(C)OC(=O)C=1N=CC=2NC3=CC=C(C=C3C=2C=1)C#CCP(=O)(OCC)OCC PUHKLTSNYMLMHH-UHFFFAOYSA-N 0.000 description 1
- OEFCKJXKGYWBAA-UHFFFAOYSA-N ethyl 6-(3-hydroxyprop-1-ynyl)-4-methyl-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C(C#CCO)C=C2C3=C(C)C(C(=O)OCC)=NC=C3NC2=C1 OEFCKJXKGYWBAA-UHFFFAOYSA-N 0.000 description 1
- MZOJZFMNTPDYAM-UHFFFAOYSA-N ethyl 6-(3-methoxyprop-1-ynyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound N1C2=CC=C(C#CCOC)C=C2C2=C1C=NC(C(=O)OCC)=C2 MZOJZFMNTPDYAM-UHFFFAOYSA-N 0.000 description 1
- IRBARSVNGQYUBQ-UHFFFAOYSA-N ethyl 6-(3-oxoprop-1-ynyl)-9H-pyrido[3,4-b]indole-3-carboxylate Chemical compound CCOC(=O)c1cc2c(cn1)[nH]c1ccc(cc21)C#CC=O IRBARSVNGQYUBQ-UHFFFAOYSA-N 0.000 description 1
- RMDZOOHVFFKPEW-UHFFFAOYSA-N ethyl 6-(azepan-1-yl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC(C2=C3)=C1NC2=CC=C3N1CCCCCC1 RMDZOOHVFFKPEW-UHFFFAOYSA-N 0.000 description 1
- QTCUESCRJQINBD-UHFFFAOYSA-N ethyl 6-(benzylamino)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC(C2=C3)=C1NC2=CC=C3NCC1=CC=CC=C1 QTCUESCRJQINBD-UHFFFAOYSA-N 0.000 description 1
- SRZMGKPJYFCKBX-UHFFFAOYSA-N ethyl 6-(dibenzylamino)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC(C2=C3)=C1NC2=CC=C3N(CC=1C=CC=CC=1)CC1=CC=CC=C1 SRZMGKPJYFCKBX-UHFFFAOYSA-N 0.000 description 1
- XXVNLKIXCPACJM-UHFFFAOYSA-N ethyl 6-(dimethylsulfamoyl)-4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C(S(=O)(=O)N(C)C)C=C2C3=C(COC)C(C(=O)OCC)=NC=C3NC2=C1 XXVNLKIXCPACJM-UHFFFAOYSA-N 0.000 description 1
- CGOWDFDTSVFKSN-UHFFFAOYSA-N ethyl 6-[3-(dimethylamino)prop-1-ynyl]-4-ethyl-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C(C#CCN(C)C)C=C2C3=C(CC)C(C(=O)OCC)=NC=C3NC2=C1 CGOWDFDTSVFKSN-UHFFFAOYSA-N 0.000 description 1
- VBANAGFCXJEBLZ-UHFFFAOYSA-N ethyl 6-[3-(oxan-2-yloxy)prop-1-ynyl]-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC(C2=C3)=C1NC2=CC=C3C#CCOC1CCCCO1 VBANAGFCXJEBLZ-UHFFFAOYSA-N 0.000 description 1
- IOQYWEKDYOLGBI-UHFFFAOYSA-N ethyl 6-[bis(2-methylprop-2-enyl)amino]-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound N1C2=CC=C(N(CC(C)=C)CC(C)=C)C=C2C2=C1C=NC(C(=O)OCC)=C2 IOQYWEKDYOLGBI-UHFFFAOYSA-N 0.000 description 1
- RLWRYLDDWSKRJN-UHFFFAOYSA-N ethyl 6-amino-4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C(N)C=C2C3=C(COC)C(C(=O)OCC)=NC=C3NC2=C1 RLWRYLDDWSKRJN-UHFFFAOYSA-N 0.000 description 1
- CVORKKPWLLMEHE-UHFFFAOYSA-N ethyl 6-amino-5-chloro-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound N1C2=CC=C(N)C(Cl)=C2C2=C1C=NC(C(=O)OCC)=C2 CVORKKPWLLMEHE-UHFFFAOYSA-N 0.000 description 1
- JBUAHEHEKCENKN-UHFFFAOYSA-N ethyl 6-amino-5-piperidin-1-yl-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC(C=23)=C1NC3=CC=C(N)C=2N1CCCCC1 JBUAHEHEKCENKN-UHFFFAOYSA-N 0.000 description 1
- GHUREMNXRLUZEU-UHFFFAOYSA-N ethyl 6-chloro-4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C(Cl)C=C2C3=C(COC)C(C(=O)OCC)=NC=C3NC2=C1 GHUREMNXRLUZEU-UHFFFAOYSA-N 0.000 description 1
- SOUPOUGCXKZPNX-UHFFFAOYSA-N ethyl 6-di(propan-2-yloxy)phosphoryl-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound N1C2=CC=C(P(=O)(OC(C)C)OC(C)C)C=C2C2=C1C=NC(C(=O)OCC)=C2 SOUPOUGCXKZPNX-UHFFFAOYSA-N 0.000 description 1
- NLPCYXPXHZLZSO-UHFFFAOYSA-N ethyl 6-diethoxyphosphoryl-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound N1C2=CC=C(P(=O)(OCC)OCC)C=C2C2=C1C=NC(C(=O)OCC)=C2 NLPCYXPXHZLZSO-UHFFFAOYSA-N 0.000 description 1
- LTYUPBZLKIUGQX-UHFFFAOYSA-N ethyl 6-iodo-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound N1C2=CC=C(I)C=C2C2=C1C=NC(C(=O)OCC)=C2 LTYUPBZLKIUGQX-UHFFFAOYSA-N 0.000 description 1
- VWLOLHAOKKIZES-UHFFFAOYSA-N ethyl 6-methoxy-4-(2-methoxyethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C(OC)C=C2C3=C(CCOC)C(C(=O)OCC)=NC=C3NC2=C1 VWLOLHAOKKIZES-UHFFFAOYSA-N 0.000 description 1
- NIZDPLDGPDAKDS-UHFFFAOYSA-N ethyl 6-nitro-5-phenylmethoxy-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC(C=23)=C1NC3=CC=C([N+]([O-])=O)C=2OCC1=CC=CC=C1 NIZDPLDGPDAKDS-UHFFFAOYSA-N 0.000 description 1
- GZZHBMSHNLABIN-UHFFFAOYSA-N ethyl 6-nitro-5-piperidin-1-yl-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC(C=23)=C1NC3=CC=C([N+]([O-])=O)C=2N1CCCCC1 GZZHBMSHNLABIN-UHFFFAOYSA-N 0.000 description 1
- IKBKLNWJNDQHFA-UHFFFAOYSA-N ethyl 6-nitro-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound N1C2=CC=C([N+]([O-])=O)C=C2C2=C1C=NC(C(=O)OCC)=C2 IKBKLNWJNDQHFA-UHFFFAOYSA-N 0.000 description 1
- QYIQUJTUQIZJAZ-UHFFFAOYSA-N ethyl 6-pyrrolidin-1-yl-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC(C2=C3)=C1NC2=CC=C3N1CCCC1 QYIQUJTUQIZJAZ-UHFFFAOYSA-N 0.000 description 1
- PRYCTVHSKQJFDW-UHFFFAOYSA-N ethyl 7-methoxy-4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound COC1=CC=C2C3=C(COC)C(C(=O)OCC)=NC=C3NC2=C1 PRYCTVHSKQJFDW-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- BNSOYWDFFBDEFB-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O BNSOYWDFFBDEFB-UHFFFAOYSA-L 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- WEAXQUBYRSEBJD-UHFFFAOYSA-N methyl 1h-indole-4-carboxylate Chemical compound COC(=O)C1=CC=CC2=C1C=CN2 WEAXQUBYRSEBJD-UHFFFAOYSA-N 0.000 description 1
- ALBSWLMUHHZLLR-UHFFFAOYSA-N methyl 2-nitroacetate Chemical compound COC(=O)C[N+]([O-])=O ALBSWLMUHHZLLR-UHFFFAOYSA-N 0.000 description 1
- WSUIYKIMSXYURD-UHFFFAOYSA-N methyl 4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound N1C2=CC=CC=C2C2=C1C=NC(C(=O)OC)=C2COC WSUIYKIMSXYURD-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- ILBIXZPOMJFOJP-UHFFFAOYSA-N n,n-dimethylprop-2-yn-1-amine Chemical compound CN(C)CC#C ILBIXZPOMJFOJP-UHFFFAOYSA-N 0.000 description 1
- AEYWPRODWLOEFK-UHFFFAOYSA-N n-methylmethanamine;pyridine Chemical compound CNC.C1=CC=NC=C1 AEYWPRODWLOEFK-UHFFFAOYSA-N 0.000 description 1
- MXOWOGWCSFJPNN-UHFFFAOYSA-N n-propan-2-ylethanimine Chemical compound CC=NC(C)C MXOWOGWCSFJPNN-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- ZOUWOGOTHLRRLS-UHFFFAOYSA-N palladium;phosphane Chemical compound P.[Pd] ZOUWOGOTHLRRLS-UHFFFAOYSA-N 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- GYMQSBJEULIXBZ-UHFFFAOYSA-N propan-2-yl 6,7-dimethoxy-4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound N1C2=CC(OC)=C(OC)C=C2C2=C1C=NC(C(=O)OC(C)C)=C2COC GYMQSBJEULIXBZ-UHFFFAOYSA-N 0.000 description 1
- DSINGDWEBKKDIE-UHFFFAOYSA-N propyl 4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=CC=C2C3=C(COC)C(C(=O)OCCC)=NC=C3NC2=C1 DSINGDWEBKKDIE-UHFFFAOYSA-N 0.000 description 1
- FJHNPORTUMDBJE-UHFFFAOYSA-N propyl 6,7-dimethoxy-4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound COC1=C(OC)C=C2C3=C(COC)C(C(=O)OCCC)=NC=C3NC2=C1 FJHNPORTUMDBJE-UHFFFAOYSA-N 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803048318 DE3048318A1 (de) | 1980-12-17 | 1980-12-17 | 4-alkoxyalkyl substituierte (beta)-carbolin-3-carbonsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| DE19813136857 DE3136857A1 (de) | 1981-09-14 | 1981-09-14 | Substituierte (beta)-carbolin-3-carbonsaeurealkylester, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8107493L SE8107493L (sv) | 1982-06-18 |
| SE446736B true SE446736B (sv) | 1986-10-06 |
Family
ID=25789905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8107493A SE446736B (sv) | 1980-12-17 | 1981-12-15 | Beta-karbolin-3-karboxylsyraderivat och framstellning derav |
Country Status (5)
| Country | Link |
|---|---|
| DK (1) | DK170504B1 (da) |
| FI (1) | FI74961C (da) |
| GR (1) | GR82311B (da) |
| NO (1) | NO159490C (da) |
| SE (1) | SE446736B (da) |
-
1981
- 1981-12-14 DK DK554281A patent/DK170504B1/da not_active IP Right Cessation
- 1981-12-14 NO NO814259A patent/NO159490C/no unknown
- 1981-12-15 SE SE8107493A patent/SE446736B/sv not_active IP Right Cessation
- 1981-12-15 GR GR66792A patent/GR82311B/el unknown
- 1981-12-16 FI FI814043A patent/FI74961C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI74961C (fi) | 1988-04-11 |
| NO814259L (no) | 1982-06-18 |
| SE8107493L (sv) | 1982-06-18 |
| DK170504B1 (da) | 1995-10-02 |
| DK554281A (da) | 1982-06-18 |
| FI814043L (fi) | 1982-06-18 |
| GR82311B (da) | 1984-12-13 |
| NO159490C (no) | 1989-01-04 |
| NO159490B (no) | 1988-09-26 |
| FI74961B (fi) | 1987-12-31 |
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