DD254201A5 - Verfahren zur herstellung von phenoxy-substituierten beta-carbolinderivaten - Google Patents

Verfahren zur herstellung von phenoxy-substituierten beta-carbolinderivaten Download PDF

Info

Publication number: DD254201A5
Authority: DD; German Democratic Republic
Prior art keywords: carboline; methoxymethyl; carboxylic acid; ethyl; chlorophenoxy
Prior art date: 1985-11-13

Application number

DD86296211A

Other languages

German (de)

English (en)

Inventor

Ralph Schmiechen

Dieter Seidelmann

Andreas Huth

Herbert H Schneider

David N Stephens

Mogens Engelstoft

John B Hansen

Erling Petersen

Original Assignee

��@��k��

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-11-13

Filing date

1986-11-12

Publication date

1988-02-17

1986-11-12 Application filed by ��@��k�� filed Critical ��@��k��

1988-02-17 Publication of DD254201A5 publication Critical patent/DD254201A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 2
AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical class N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 title 1
-1 phenoxy-substituted b-carboline Chemical class 0.000 claims abstract description 232
125000000217 alkyl group Chemical group 0.000 claims abstract description 20
229910052736 halogen Inorganic materials 0.000 claims abstract description 12
150000002367 halogens Chemical class 0.000 claims abstract description 12
239000001257 hydrogen Substances 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
125000002252 acyl group Chemical group 0.000 claims abstract description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 3
125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
125000005530 alkylenedioxy group Chemical group 0.000 claims abstract description 3
125000002648 azanetriyl group Chemical group *N(*)* 0.000 claims abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 claims description 40
150000001875 compounds Chemical class 0.000 claims description 38
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 32
239000000203 mixture Substances 0.000 claims description 11
238000000034 method Methods 0.000 claims description 10
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 6
QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
125000004185 ester group Chemical group 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
150000001540 azides Chemical class 0.000 claims description 3
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 3
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229910052740 iodine Inorganic materials 0.000 claims description 3
UGRMITBWUVWUEB-UHFFFAOYSA-N 1-$l^{1}-oxidanyl-3-methylbenzene Chemical group CC1=CC=CC([O])=C1 UGRMITBWUVWUEB-UHFFFAOYSA-N 0.000 claims description 2
150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
ARCSBFATIFHVTF-UHFFFAOYSA-N 3-ethyl-1,2,4-oxadiazole Chemical compound CCC=1N=CON=1 ARCSBFATIFHVTF-UHFFFAOYSA-N 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 abstract description 5
238000002844 melting Methods 0.000 description 108
230000008018 melting Effects 0.000 description 108
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239000000243 solution Substances 0.000 description 11
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
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238000006243 chemical reaction Methods 0.000 description 7
230000000694 effects Effects 0.000 description 7
239000000126 substance Substances 0.000 description 7
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239000003480 eluent Substances 0.000 description 6
XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
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239000003054 catalyst Substances 0.000 description 5
229960002200 flunitrazepam Drugs 0.000 description 5
239000002904 solvent Substances 0.000 description 5
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238000006073 displacement reaction Methods 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
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239000000725 suspension Substances 0.000 description 4
238000005809 transesterification reaction Methods 0.000 description 4
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
206010010904 Convulsion Diseases 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
102000004300 GABA-A Receptors Human genes 0.000 description 3
108090000839 GABA-A Receptors Proteins 0.000 description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 3
PPTYJKAXVCCBDU-UHFFFAOYSA-N Rohypnol Chemical compound N=1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1F PPTYJKAXVCCBDU-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
239000000010 aprotic solvent Substances 0.000 description 3
210000004556 brain Anatomy 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
210000003169 central nervous system Anatomy 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000012954 diazonium Substances 0.000 description 3
150000001989 diazonium salts Chemical class 0.000 description 3
239000003814 drug Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
238000007911 parenteral administration Methods 0.000 description 3
WUHLVXDDBHWHLQ-UHFFFAOYSA-N pentazole Chemical compound N=1N=NNN=1 WUHLVXDDBHWHLQ-UHFFFAOYSA-N 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
230000000506 psychotropic effect Effects 0.000 description 3
238000010992 reflux Methods 0.000 description 3
WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 2
FBAOVPVVMDOHPK-UHFFFAOYSA-N 2-(1h-imidazol-2-ylsulfinyl)-1h-imidazole Chemical compound N=1C=CNC=1S(=O)C1=NC=CN1 FBAOVPVVMDOHPK-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
ARLVFKCLBYUINL-UHFFFAOYSA-N 9h-pyrido[3,4-b]indole-3-carboxylic acid Chemical compound N1C2=CC=CC=C2C2=C1C=NC(C(=O)O)=C2 ARLVFKCLBYUINL-UHFFFAOYSA-N 0.000 description 2
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-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
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
241001465754 Metazoa Species 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
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NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
241000700159 Rattus Species 0.000 description 2
230000004913 activation Effects 0.000 description 2
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230000001773 anti-convulsant effect Effects 0.000 description 2
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238000009835 boiling Methods 0.000 description 2
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229910052794 bromium Inorganic materials 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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238000006482 condensation reaction Methods 0.000 description 2
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239000010949 copper Substances 0.000 description 2
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235000014113 dietary fatty acids Nutrition 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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239000011261 inert gas Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000011630 iodine Substances 0.000 description 2
239000008101 lactose 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
239000012528 membrane Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
RLZPCFQNZGINRP-UHFFFAOYSA-N n'-hydroxypropanimidamide Chemical compound CCC(N)=NO RLZPCFQNZGINRP-UHFFFAOYSA-N 0.000 description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 2
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239000002244 precipitate Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
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239000004089 psychotropic agent Substances 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
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239000007858 starting material Substances 0.000 description 2
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229910052623 talc Inorganic materials 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
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CAJDBSWZROJJPP-UHFFFAOYSA-N 5-[6-(4-chlorophenoxy)-4-(methoxymethyl)-9h-pyrido[3,4-b]indol-3-yl]-3-ethyl-1,2,4-oxadiazole Chemical compound CCC1=NOC(C=2C(=C3C4=CC(OC=5C=CC(Cl)=CC=5)=CC=C4NC3=CN=2)COC)=N1 CAJDBSWZROJJPP-UHFFFAOYSA-N 0.000 description 1
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208000007101 Muscle Cramp Diseases 0.000 description 1
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PFMSDSLUALYMMP-UHFFFAOYSA-N N'-hydroxy-9H-pyrido[3,4-b]indole-3-carboximidamide Chemical compound N1C2=CC=CC=C2C2=C1C=NC(C(=NO)N)=C2 PFMSDSLUALYMMP-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
238000000297 Sandmeyer reaction Methods 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
208000005392 Spasm Diseases 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical compound [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 description 1
206010043994 Tonic convulsion Diseases 0.000 description 1
241000251539 Vertebrata <Metazoa> Species 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
230000009435 amidation Effects 0.000 description 1
238000007112 amidation reaction Methods 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
229960003965 antiepileptics Drugs 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
239000002249 anxiolytic agent Substances 0.000 description 1
230000000949 anxiolytic effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
150000001557 benzodiazepines Chemical class 0.000 description 1
230000027455 binding Effects 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003518 caustics Substances 0.000 description 1
SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
230000002566 clonic effect Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
150000003983 crown ethers Chemical class 0.000 description 1
239000013078 crystal Substances 0.000 description 1
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125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
230000009615 deamination Effects 0.000 description 1
238000006481 deamination reaction Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000005695 dehalogenation reaction Methods 0.000 description 1
229960003529 diazepam Drugs 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 1
BBGKDYHZQOSNMU-UHFFFAOYSA-N dicyclohexano-18-crown-6 Chemical compound O1CCOCCOC2CCCCC2OCCOCCOC2CCCCC21 BBGKDYHZQOSNMU-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
206010015037 epilepsy Diseases 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
WCDZUGVKCUVOCO-UHFFFAOYSA-N ethyl 4-ethyl-6-(2-nitrophenoxy)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C2C3=C(CC)C(C(=O)OCC)=NC=C3NC2=CC=C1OC1=CC=CC=C1[N+]([O-])=O WCDZUGVKCUVOCO-UHFFFAOYSA-N 0.000 description 1
TWYLSBATIICROG-UHFFFAOYSA-N ethyl 5-(4-aminophenoxy)-4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C=12C3=C(COC)C(C(=O)OCC)=NC=C3NC2=CC=CC=1OC1=CC=C(N)C=C1 TWYLSBATIICROG-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000008423 fluorobenzenes Chemical class 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
239000007789 gas Substances 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
239000011521 glass Substances 0.000 description 1
150000005171 halobenzenes Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
150000007928 imidazolide derivatives Chemical class 0.000 description 1
125000002632 imidazolidinyl group Chemical group 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
230000036640 muscle relaxation Effects 0.000 description 1
HXRAMSFGUAOAJR-UHFFFAOYSA-N n,n,n',n'-tetramethyl-1-[(2-methylpropan-2-yl)oxy]methanediamine Chemical compound CN(C)C(N(C)C)OC(C)(C)C HXRAMSFGUAOAJR-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002826 nitrites Chemical class 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001223 polyethylene glycol 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
229910000027 potassium carbonate Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
RUWFMBHSVSKCIA-UHFFFAOYSA-N propan-2-yl 6-(4-amino-3-methoxyphenoxy)-4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C2C=3C(COC)=C(C(=O)OC(C)C)N=CC=3NC2=CC=C1OC1=CC=C(N)C(OC)=C1 RUWFMBHSVSKCIA-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000003345 scintillation counting 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
208000019116 sleep disease Diseases 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
208000018198 spasticity Diseases 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
229910052717 sulfur Inorganic materials 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
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Neurosurgery (AREA)
Life Sciences & Earth Sciences (AREA)
Neurology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Pain & Pain Management (AREA)
Anesthesiology (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Photoreceptors In Electrophotography (AREA)

DD86296211A 1985-11-13 1986-11-12 Verfahren zur herstellung von phenoxy-substituierten beta-carbolinderivaten DD254201A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19853540654 DE3540654A1 (de)	1985-11-13	1985-11-13	Phenoxy-substituierte ss-carbolinderivate, ihre herstellung und ihre verwendung als arzneimittel

Publications (1)

Publication Number	Publication Date
DD254201A5 true DD254201A5 (de)	1988-02-17

Family

ID=6286132

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86296211A DD254201A5 (de)	1985-11-13	1986-11-12	Verfahren zur herstellung von phenoxy-substituierten beta-carbolinderivaten

Country Status (18)

Country	Link
US (1)	US4945090A (da)
EP (1)	EP0234173B1 (da)
JP (1)	JPH0699431B2 (da)
AT (1)	ATE90678T1 (da)
AU (1)	AU602497B2 (da)
CA (1)	CA1269377A (da)
DD (1)	DD254201A5 (da)
DE (2)	DE3540654A1 (da)
DK (1)	DK169702B1 (da)
ES (1)	ES2058064T3 (da)
FI (1)	FI84067C (da)
HU (1)	HU198046B (da)
IE (1)	IE61661B1 (da)
IL (1)	IL80618A (da)
NO (1)	NO163736C (da)
NZ (1)	NZ218244A (da)
PT (1)	PT83726B (da)
ZA (1)	ZA868631B (da)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3540654A1 (de) *	1985-11-13	1987-05-14	Schering Ag	Phenoxy-substituierte ss-carbolinderivate, ihre herstellung und ihre verwendung als arzneimittel
DE3540653A1 (de) *	1985-11-13	1987-05-14	Schering Ag	Neue 3-oxadiazol- und 3-carbonsaeure-ss-carbolinderivate, ihre herstellung und ihre verwendung als arzneimittel
DE3608089A1 (de) *	1986-03-08	1987-09-10	Schering Ag	Heteroaryl-oxy-ss-carbolinderivate, ihre herstellung und ihre verwendung als arzneimittel
DE3730667A1 (de) *	1987-09-09	1989-03-23	Schering Ag	Neue ss-carboline
DE3729370C2 (de) *	1987-08-31	1995-04-20	Schering Ag	Verfahren zur Herstellung von 4-Alkoxyalkyl-beta-carbolinen
DE4029389A1 (de) *	1990-09-13	1992-03-26	Schering Ag	Verfahren zur herstellung von (beta)-carbolin-derivaten
DE4109342A1 (de) *	1991-03-19	1992-09-24	Schering Ag	Selektive phenylierung von 5-hydroxy-ss-carbolinderivaten
US5350750A (en) *	1991-04-27	1994-09-27	Schering Aktiengesellschaft	β-carboline-3-hydroxyalkylcarboxylic acid ester derivatives, process for their production and their use in pharmaceutical agents
DE4120109A1 (de) *	1991-06-15	1992-12-17	Schering Ag	3-aryl- oder 3-hetaryl-(beta)-carboline, deren herstellung und verwendung in arzneimitteln
US5543519A (en) *	1991-06-15	1996-08-06	Schering Aktiengesellschaft	3-aryl or 3-hetaryl-β-carbolines, their production and use in pharmaceutical agents
PE20120008A1 (es) *	2009-01-12	2012-01-24	Icagen Inc	Derivados de fenoxi bencenosulfonamida
JP5872552B2 (ja)	2010-07-09	2016-03-01	ファイザー・リミテッドＰｆｉｚｅｒＬｉｍｉｔｅｄ	化学化合物

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS57123180A (en)	1980-12-17	1982-07-31	Schering Ag	3-substituted beta-carboline, manufacture and psychotropic drug containing same
DE3322895A1 (de)	1983-06-23	1985-01-03	Schering AG, 1000 Berlin und 4709 Bergkamen	Neue ss-carboline, verfahren zur ihrer herstellung und ihre verwendung als arzneimittel (s)
DE3504045A1 (de) *	1985-02-04	1986-08-07	Schering AG, 1000 Berlin und 4709 Bergkamen	Verfahren zur herstellung von ss-carbolinen durch dehydrierung
DE3540654A1 (de) *	1985-11-13	1987-05-14	Schering Ag	Phenoxy-substituierte ss-carbolinderivate, ihre herstellung und ihre verwendung als arzneimittel

1985
- 1985-11-13 DE DE19853540654 patent/DE3540654A1/de not_active Withdrawn
1986
- 1986-11-11 DE DE8686730188T patent/DE3688594D1/de not_active Expired - Lifetime
- 1986-11-11 NZ NZ218244A patent/NZ218244A/xx unknown
- 1986-11-11 AT AT86730188T patent/ATE90678T1/de active
- 1986-11-11 EP EP86730188A patent/EP0234173B1/de not_active Expired - Lifetime
- 1986-11-11 ES ES86730188T patent/ES2058064T3/es not_active Expired - Lifetime
- 1986-11-12 DD DD86296211A patent/DD254201A5/de not_active IP Right Cessation
- 1986-11-12 PT PT83726A patent/PT83726B/pt not_active IP Right Cessation
- 1986-11-12 HU HU864678A patent/HU198046B/hu not_active IP Right Cessation
- 1986-11-12 NO NO864517A patent/NO163736C/no unknown
- 1986-11-12 IL IL80618A patent/IL80618A/xx not_active IP Right Cessation
- 1986-11-12 CA CA000522771A patent/CA1269377A/en not_active Expired - Lifetime
- 1986-11-13 IE IE299686A patent/IE61661B1/en not_active IP Right Cessation
- 1986-11-13 US US06/929,861 patent/US4945090A/en not_active Expired - Fee Related
- 1986-11-13 JP JP61268799A patent/JPH0699431B2/ja not_active Expired - Lifetime
- 1986-11-13 AU AU65170/86A patent/AU602497B2/en not_active Ceased
- 1986-11-13 DK DK543886A patent/DK169702B1/da not_active IP Right Cessation
- 1986-11-13 ZA ZA868631A patent/ZA868631B/xx unknown
- 1986-11-13 FI FI864619A patent/FI84067C/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
US4945090A (en)	1990-07-31
EP0234173A2 (de)	1987-09-02
AU602497B2 (en)	1990-10-18
IL80618A0 (en)	1987-02-27
IE61661B1 (en)	1994-11-16
DK543886A (da)	1987-05-14
ZA868631B (en)	1987-06-24
ATE90678T1 (de)	1993-07-15
CA1269377A (en)	1990-05-22
DE3688594D1 (de)	1993-07-22
IE862996L (en)	1987-05-13
AU6517086A (en)	1987-05-21
FI84067B (fi)	1991-06-28
FI864619A0 (fi)	1986-11-13
NO163736C (no)	1990-07-11
FI864619A7 (fi)	1987-05-14
EP0234173B1 (de)	1993-06-16
ES2058064T3 (es)	1994-11-01
NO864517L (no)	1987-05-14
DK543886D0 (da)	1986-11-13
PT83726B (pt)	1989-05-12
NO163736B (no)	1990-04-02
PT83726A (en)	1986-12-01
HUT43067A (en)	1987-09-28
HU198046B (en)	1989-07-28
FI84067C (fi)	1991-10-10
IL80618A (en)	1990-09-17
NZ218244A (en)	1990-05-28
EP0234173A3 (en)	1988-07-06
DE3540654A1 (de)	1987-05-14
JPH0699431B2 (ja)	1994-12-07
JPS62167780A (ja)	1987-07-24
DK169702B1 (da)	1995-01-16
NO864517D0 (no)	1986-11-12

Legal Events

Date	Code	Title	Description
1995-02-16	VZ	Disclaimer of patent (art. 11 and 12 extension act)
1995-03-02	VZ	Disclaimer of patent (art. 11 and 12 extension act)

Publication	Publication Date	Title
DE3107601C2 (da)	1989-07-20
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DE2737630A1 (de)	1979-03-01	Neue aminopropanolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
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