DE2509683A1 - Cyclopentan-1,2,3,4-tetrahydroisochinoline - Google Patents
Cyclopentan-1,2,3,4-tetrahydroisochinolineInfo
- Publication number
- DE2509683A1 DE2509683A1 DE19752509683 DE2509683A DE2509683A1 DE 2509683 A1 DE2509683 A1 DE 2509683A1 DE 19752509683 DE19752509683 DE 19752509683 DE 2509683 A DE2509683 A DE 2509683A DE 2509683 A1 DE2509683 A1 DE 2509683A1
- Authority
- DE
- Germany
- Prior art keywords
- deep
- compound
- dimethoxy
- formula
- hydrogen
- 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.)
- Pending
Links
- -1 CYCLOPENTAN-1,2,3,4-TETRAHYDROISOCHINOLINE Chemical compound 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims description 42
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- ITDHODBHQNVRFW-UHFFFAOYSA-N 4,5-dimethoxy-6-(2-nitroethenyl)-2,3-dihydro-1h-indene Chemical compound [O-][N+](=O)C=CC1=C(OC)C(OC)=C2CCCC2=C1 ITDHODBHQNVRFW-UHFFFAOYSA-N 0.000 claims description 5
- CPNJBAMJTFVFFF-UHFFFAOYSA-N 4,5-dimethoxy-7-(2-nitroethenyl)-2,3-dihydro-1h-indene Chemical compound COC1=CC(C=C[N+]([O-])=O)=C2CCCC2=C1OC CPNJBAMJTFVFFF-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- WQJWIMOQQFIBOM-UHFFFAOYSA-N n-[2-(6,7-dimethoxy-2,3-dihydro-1h-inden-4-yl)ethyl]methanimine Chemical compound COC1=CC(CCN=C)=C2CCCC2=C1OC WQJWIMOQQFIBOM-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- RWZRXYNTLDHQRZ-UHFFFAOYSA-N n-[2-(6,7-dimethoxy-2,3-dihydro-1h-inden-5-yl)ethyl]methanimine Chemical compound C=NCCC1=C(OC)C(OC)=C2CCCC2=C1 RWZRXYNTLDHQRZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 229940127557 pharmaceutical product Drugs 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims 2
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- 229960000583 acetic acid Drugs 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 150000001299 aldehydes Chemical class 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 230000036772 blood pressure Effects 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- CKKAOFMMFNPZPR-UHFFFAOYSA-N 6,7-dimethoxy-2,3-dihydro-1h-indene-5-carbaldehyde Chemical compound O=CC1=C(OC)C(OC)=C2CCCC2=C1 CKKAOFMMFNPZPR-UHFFFAOYSA-N 0.000 description 6
- 239000002262 Schiff base Substances 0.000 description 6
- 150000004753 Schiff bases Chemical class 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- OYPVPAXDSIDUQG-UHFFFAOYSA-N 4,5-dimethoxy-2,3-dihydro-1h-indene Chemical compound COC1=CC=C2CCCC2=C1OC OYPVPAXDSIDUQG-UHFFFAOYSA-N 0.000 description 5
- KHVRKYOQRGQIRY-UHFFFAOYSA-N 6,7-dimethoxy-2,3-dihydro-1h-indene-4-carbaldehyde Chemical compound COC1=CC(C=O)=C2CCCC2=C1OC KHVRKYOQRGQIRY-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
- 239000005695 Ammonium acetate Substances 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- 229940043376 ammonium acetate Drugs 0.000 description 4
- 235000019257 ammonium acetate Nutrition 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 150000002468 indanes Chemical class 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- HWTJUAINQVAQDN-UHFFFAOYSA-N 2-(6,7-dimethoxy-2,3-dihydro-1h-inden-5-yl)ethanamine Chemical compound NCCC1=C(OC)C(OC)=C2CCCC2=C1 HWTJUAINQVAQDN-UHFFFAOYSA-N 0.000 description 3
- XQODIRIVQXQUFN-UHFFFAOYSA-N 4,5-dimethoxy-2,3-dihydroinden-1-one Chemical compound COC1=CC=C2C(=O)CCC2=C1OC XQODIRIVQXQUFN-UHFFFAOYSA-N 0.000 description 3
- 229910010082 LiAlH Inorganic materials 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000011260 aqueous acid Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N benzocyclopentane Natural products C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 2
- VNWQQFOZEKADBU-UHFFFAOYSA-N 2-(6,7-dimethoxy-2,3-dihydro-1h-inden-4-yl)ethanamine Chemical compound COC1=CC(CCN)=C2CCCC2=C1OC VNWQQFOZEKADBU-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 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
- 206010020772 Hypertension Diseases 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000006929 Pictet-Spengler synthesis reaction Methods 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000538 analytical sample Substances 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 230000001631 hypertensive effect Effects 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 150000002537 isoquinolines Chemical class 0.000 description 2
- 239000012280 lithium aluminium hydride 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
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000004971 nitroalkyl group Chemical group 0.000 description 2
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 230000035488 systolic blood pressure Effects 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 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
- 238000005406 washing Methods 0.000 description 2
- 230000003313 weakening effect Effects 0.000 description 2
- VZJSCBVJXIHTIY-UHFFFAOYSA-N 1-(6,7-diethoxy-2,3-dihydro-1h-inden-5-yl)propan-2-amine Chemical compound CC(N)CC1=C(OCC)C(OCC)=C2CCCC2=C1 VZJSCBVJXIHTIY-UHFFFAOYSA-N 0.000 description 1
- ATYVGMRNNKLFFA-UHFFFAOYSA-N 1-(6,7-dipropoxy-2,3-dihydro-1h-inden-4-yl)butan-2-amine Chemical compound CCCOC1=CC(CC(N)CC)=C2CCCC2=C1OCCC ATYVGMRNNKLFFA-UHFFFAOYSA-N 0.000 description 1
- ITBTVUBHMLFDJV-UHFFFAOYSA-N 1-(6,7-dipropoxy-2,3-dihydro-1h-inden-5-yl)butan-2-amine Chemical compound CCC(N)CC1=C(OCCC)C(OCCC)=C2CCCC2=C1 ITBTVUBHMLFDJV-UHFFFAOYSA-N 0.000 description 1
- WFYSSTHMJYADMI-UHFFFAOYSA-N 2-(6-ethoxy-7-methoxy-2,3-dihydro-1h-inden-4-yl)ethanamine Chemical compound CCOC1=CC(CCN)=C2CCCC2=C1OC WFYSSTHMJYADMI-UHFFFAOYSA-N 0.000 description 1
- YNMDENKWNSWIEE-UHFFFAOYSA-N 2-(6-ethoxy-7-methoxy-2,3-dihydro-1h-inden-5-yl)ethanamine Chemical compound CCOC1=C(CCN)C=C2CCCC2=C1OC YNMDENKWNSWIEE-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ACUKSMLNQJTHEL-UHFFFAOYSA-N 4,5-di(propan-2-yloxy)-2,3-dihydro-1h-indene Chemical compound CC(C)OC1=CC=C2CCCC2=C1OC(C)C ACUKSMLNQJTHEL-UHFFFAOYSA-N 0.000 description 1
- OSJAAUGCWFHJEW-UHFFFAOYSA-N 4,5-dibutoxy-2,3-dihydro-1h-indene Chemical compound CCCCOC1=CC=C2CCCC2=C1OCCCC OSJAAUGCWFHJEW-UHFFFAOYSA-N 0.000 description 1
- RIHNBVJSAXNNLW-UHFFFAOYSA-N 4,5-diethoxy-2,3-dihydro-1h-indene Chemical compound CCOC1=CC=C2CCCC2=C1OCC RIHNBVJSAXNNLW-UHFFFAOYSA-N 0.000 description 1
- IODGIRMGLDCAFV-UHFFFAOYSA-N 4,5-diethoxy-2,3-dihydroinden-1-one Chemical compound CCOC1=CC=C2C(=O)CCC2=C1OCC IODGIRMGLDCAFV-UHFFFAOYSA-N 0.000 description 1
- PVJVBZSGGACUNX-UHFFFAOYSA-N 4,5-diethoxy-6-(2-nitroethenyl)-2,3-dihydro-1h-indene Chemical compound [O-][N+](=O)C=CC1=C(OCC)C(OCC)=C2CCCC2=C1 PVJVBZSGGACUNX-UHFFFAOYSA-N 0.000 description 1
- JQXASNXFUUDUDW-UHFFFAOYSA-N 4,5-diethoxy-7-(2-nitroethenyl)-2,3-dihydro-1h-indene Chemical compound CCOC1=CC(C=C[N+]([O-])=O)=C2CCCC2=C1OCC JQXASNXFUUDUDW-UHFFFAOYSA-N 0.000 description 1
- KKFKNHZKYJKKFF-UHFFFAOYSA-N 4,5-dimethoxy-6-(2-nitrobut-1-enyl)-2,3-dihydro-1h-indene Chemical compound COC1=C(OC)C(C=C(CC)[N+]([O-])=O)=CC2=C1CCC2 KKFKNHZKYJKKFF-UHFFFAOYSA-N 0.000 description 1
- OKNVTTUULKFFDQ-UHFFFAOYSA-N 4,5-dimethoxy-6-(2-nitroprop-1-enyl)-2,3-dihydro-1h-indene Chemical compound [O-][N+](=O)C(C)=CC1=C(OC)C(OC)=C2CCCC2=C1 OKNVTTUULKFFDQ-UHFFFAOYSA-N 0.000 description 1
- YDGQWORTJYRSLN-UHFFFAOYSA-N 4,5-dimethoxy-7-(2-nitrobut-1-enyl)-2,3-dihydro-1h-indene Chemical compound CCC([N+]([O-])=O)=CC1=CC(OC)=C(OC)C2=C1CCC2 YDGQWORTJYRSLN-UHFFFAOYSA-N 0.000 description 1
- INBAOLFKFLYIAV-UHFFFAOYSA-N 4,5-dimethoxy-7-(2-nitroprop-1-enyl)-2,3-dihydro-1h-indene Chemical compound COC1=CC(C=C(C)[N+]([O-])=O)=C2CCCC2=C1OC INBAOLFKFLYIAV-UHFFFAOYSA-N 0.000 description 1
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- IAHFDSKTWWTXGE-UHFFFAOYSA-N 4,5-dipropoxy-2,3-dihydroinden-1-one Chemical compound CCCOC1=CC=C2C(=O)CCC2=C1OCCC IAHFDSKTWWTXGE-UHFFFAOYSA-N 0.000 description 1
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- CNDZXXYCHQSGOA-UHFFFAOYSA-N 5-ethoxy-4-methoxy-2,3-dihydro-1h-indene Chemical compound CCOC1=CC=C2CCCC2=C1OC CNDZXXYCHQSGOA-UHFFFAOYSA-N 0.000 description 1
- HOEQJFXFNVLWPC-UHFFFAOYSA-N 5-ethoxy-4-methoxy-2,3-dihydroinden-1-one Chemical compound CCOC1=CC=C2C(=O)CCC2=C1OC HOEQJFXFNVLWPC-UHFFFAOYSA-N 0.000 description 1
- SOVHOTUGQVOWAY-UHFFFAOYSA-N 5-ethoxy-4-methoxy-6-(2-nitroethenyl)-2,3-dihydro-1h-indene Chemical compound C1=C(C=C[N+]([O-])=O)C(OCC)=C(OC)C2=C1CCC2 SOVHOTUGQVOWAY-UHFFFAOYSA-N 0.000 description 1
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- IQIQEKYONZFVIR-UHFFFAOYSA-N 6,7-diethoxy-2,3-dihydro-1h-indene-4-carbaldehyde Chemical compound CCOC1=CC(C=O)=C2CCCC2=C1OCC IQIQEKYONZFVIR-UHFFFAOYSA-N 0.000 description 1
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- 125000003172 aldehyde group Chemical group 0.000 description 1
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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- 238000010411 cooking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 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
- 239000008187 granular material Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000008297 liquid dosage form Substances 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
- 238000004519 manufacturing process Methods 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
- JOZOFRLWWRSVIP-UHFFFAOYSA-N n-[1-(6,7-diethoxy-2,3-dihydro-1h-inden-4-yl)propan-2-yl]methanimine Chemical compound CCOC1=CC(CC(C)N=C)=C2CCCC2=C1OCC JOZOFRLWWRSVIP-UHFFFAOYSA-N 0.000 description 1
- VODOAGDHEKAIOI-UHFFFAOYSA-N n-[1-(6,7-diethoxy-2,3-dihydro-1h-inden-5-yl)propan-2-yl]methanimine Chemical compound C=NC(C)CC1=C(OCC)C(OCC)=C2CCCC2=C1 VODOAGDHEKAIOI-UHFFFAOYSA-N 0.000 description 1
- KRTCNRRLJANNSH-UHFFFAOYSA-N n-[1-(6,7-dipropoxy-2,3-dihydro-1h-inden-4-yl)butan-2-yl]methanimine Chemical compound CCCOC1=CC(CC(CC)N=C)=C2CCCC2=C1OCCC KRTCNRRLJANNSH-UHFFFAOYSA-N 0.000 description 1
- ORYHODJWDKTVSD-UHFFFAOYSA-N n-[1-(6,7-dipropoxy-2,3-dihydro-1h-inden-5-yl)butan-2-yl]methanimine Chemical compound CCC(N=C)CC1=C(OCCC)C(OCCC)=C2CCCC2=C1 ORYHODJWDKTVSD-UHFFFAOYSA-N 0.000 description 1
- HAZUHYBLWNRTAA-UHFFFAOYSA-N n-[2-(6-ethoxy-7-methoxy-2,3-dihydro-1h-inden-4-yl)ethyl]methanimine Chemical compound CCOC1=CC(CCN=C)=C2CCCC2=C1OC HAZUHYBLWNRTAA-UHFFFAOYSA-N 0.000 description 1
- PKARWZJCORZVSH-UHFFFAOYSA-N n-[2-(6-ethoxy-7-methoxy-2,3-dihydro-1h-inden-5-yl)ethyl]methanimine Chemical compound CCOC1=C(CCN=C)C=C2CCCC2=C1OC PKARWZJCORZVSH-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/455,574 US3963723A (en) | 1974-03-28 | 1974-03-28 | Cyclopentano (h) or (f) 1,2,3,4-tetrahydroisoquinolines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2509683A1 true DE2509683A1 (de) | 1975-10-09 |
Family
ID=23809386
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752509683 Pending DE2509683A1 (de) | 1974-03-28 | 1975-03-06 | Cyclopentan-1,2,3,4-tetrahydroisochinoline |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3963723A (en, 2012) |
| JP (1) | JPS50154433A (en, 2012) |
| BE (1) | BE827283A (en, 2012) |
| CA (1) | CA1063117A (en, 2012) |
| DE (1) | DE2509683A1 (en, 2012) |
| DK (1) | DK120975A (en, 2012) |
| FR (1) | FR2265378B1 (en, 2012) |
| IL (1) | IL46812A0 (en, 2012) |
| NL (1) | NL7503706A (en, 2012) |
| SE (1) | SE7503728L (en, 2012) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3541158A (en) * | 1967-12-19 | 1970-11-17 | Dow Chemical Co | 1-(di(lower alkoxy)-4-alkylphenyl)-2-nitropropenes |
-
1974
- 1974-03-28 US US05/455,574 patent/US3963723A/en not_active Expired - Lifetime
-
1975
- 1975-03-06 DE DE19752509683 patent/DE2509683A1/de active Pending
- 1975-03-12 IL IL46812A patent/IL46812A0/xx unknown
- 1975-03-20 JP JP50034204A patent/JPS50154433A/ja active Pending
- 1975-03-21 DK DK120975A patent/DK120975A/da unknown
- 1975-03-27 NL NL7503706A patent/NL7503706A/xx not_active Application Discontinuation
- 1975-03-27 CA CA223,273A patent/CA1063117A/en not_active Expired
- 1975-03-27 BE BE154857A patent/BE827283A/xx unknown
- 1975-03-27 FR FR7509663A patent/FR2265378B1/fr not_active Expired
- 1975-04-01 SE SE7503728A patent/SE7503728L/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2265378B1 (en, 2012) | 1980-01-25 |
| CA1063117A (en) | 1979-09-25 |
| FR2265378A1 (en, 2012) | 1975-10-24 |
| JPS50154433A (en, 2012) | 1975-12-12 |
| NL7503706A (nl) | 1975-09-30 |
| DK120975A (en, 2012) | 1975-09-29 |
| BE827283A (fr) | 1975-07-16 |
| IL46812A0 (en) | 1975-05-22 |
| US3963723A (en) | 1976-06-15 |
| SE7503728L (en, 2012) | 1975-09-29 |
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