CH493520A - Verfahren zur Herstellung von 1-Phenoxymethyl-3,4-dihydroisochinolinen und ihren Säureanlagerungssalzen - Google Patents

Verfahren zur Herstellung von 1-Phenoxymethyl-3,4-dihydroisochinolinen und ihren Säureanlagerungssalzen

Info

Publication number: CH493520A
Authority: CH; Switzerland
Prior art keywords: acid; dihydroisoquinoline; phenoxymethyl; hydrogen; hydrochloride
Prior art date: 1964-12-18

Application number

CH1738465A

Other languages

German (de)

English (en)

Inventor

Roy Gildersleve David

Shilton Tute Michael

Original Assignee

Pfizer

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.)

1964-12-18

Filing date

1965-12-16

Publication date

1970-07-15

1965-12-16 Application filed by Pfizer filed Critical Pfizer

1970-07-15 Publication of CH493520A publication Critical patent/CH493520A/de

Links

AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 title 2
230000000840 anti-viral effect Effects 0.000 title 1
239000002253 acid Substances 0.000 claims abstract description 16
150000003839 salts Chemical class 0.000 claims abstract description 12
229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
150000007513 acids Chemical class 0.000 claims abstract description 5
229910052794 bromium Inorganic materials 0.000 claims abstract description 3
229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims abstract 4
238000000034 method Methods 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
VTHPMBVZXKLEQS-UHFFFAOYSA-N 1-(phenoxymethyl)-3,4-dihydroisoquinoline Chemical class N=1CCC2=CC=CC=C2C=1COC1=CC=CC=C1 VTHPMBVZXKLEQS-UHFFFAOYSA-N 0.000 claims description 4
239000007858 starting material Substances 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 3
239000012024 dehydrating agents‎ Substances 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 3
150000002431 hydrogen Chemical group 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
239000012442 inert solvent Substances 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
231100000252 nontoxic Toxicity 0.000 abstract description 6
230000003000 nontoxic effect Effects 0.000 abstract description 6
241000712461 unidentified influenza virus Species 0.000 abstract description 4
125000003545 alkoxy group Chemical group 0.000 abstract 1
239000003443 antiviral agent Substances 0.000 abstract 1
-1 alkyl radicals Chemical class 0.000 description 25
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
235000002639 sodium chloride Nutrition 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000002585 base Substances 0.000 description 7
239000000243 solution Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 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
239000007864 aqueous solution Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
YHDHSSBAHPSMPM-UHFFFAOYSA-N 1-[(4-chlorophenoxy)methyl]-3,4-dihydroisoquinoline Chemical compound C1=CC(Cl)=CC=C1OCC1=NCCC2=CC=CC=C12 YHDHSSBAHPSMPM-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
239000000969 carrier Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 4
239000012458 free base Substances 0.000 description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
241000700605 Viruses Species 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
150000004682 monohydrates Chemical class 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000003826 tablet Substances 0.000 description 3
XWPQCMLTRJWFKB-UHFFFAOYSA-N 1-[(4-chlorophenoxy)methyl]-3,4-dihydroisoquinoline;hydrochloride Chemical compound Cl.C1=CC(Cl)=CC=C1OCC1=NCCC2=CC=CC=C12 XWPQCMLTRJWFKB-UHFFFAOYSA-N 0.000 description 2
XUMWBPBVHHGEFI-UHFFFAOYSA-N 1-[(4-fluorophenoxy)methyl]-3,4-dihydroisoquinoline Chemical compound C1=CC(F)=CC=C1OCC1=NCCC2=CC=CC=C12 XUMWBPBVHHGEFI-UHFFFAOYSA-N 0.000 description 2
NOCSCLPQKGWLDB-UHFFFAOYSA-N 1-[(4-methoxyphenoxy)methyl]-3,4-dihydroisoquinoline Chemical compound C1=CC(OC)=CC=C1OCC1=NCCC2=CC=CC=C12 NOCSCLPQKGWLDB-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
229940092714 benzenesulfonic acid Drugs 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
235000015165 citric acid Nutrition 0.000 description 2
230000000694 effects Effects 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
229940071870 hydroiodic acid Drugs 0.000 description 2
239000004310 lactic acid Substances 0.000 description 2
235000014655 lactic acid Nutrition 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
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
238000003860 storage Methods 0.000 description 2
239000011975 tartaric acid Substances 0.000 description 2
235000002906 tartaric acid Nutrition 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 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
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
IOEPOEDBBPRAEI-UHFFFAOYSA-N 1,2-dihydroisoquinoline Chemical compound C1=CC=C2CNC=CC2=C1 IOEPOEDBBPRAEI-UHFFFAOYSA-N 0.000 description 1
LFFGEYHTAJZONR-UHFFFAOYSA-N 1-[(4-methoxyphenoxy)methyl]-3,4-dihydroisoquinoline;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1OCC1=NCCC2=CC=CC=C12 LFFGEYHTAJZONR-UHFFFAOYSA-N 0.000 description 1
VRBVHQUSAOKVDH-UHFFFAOYSA-N 2-(4-chlorophenoxy)acetyl chloride Chemical compound ClC(=O)COC1=CC=C(Cl)C=C1 VRBVHQUSAOKVDH-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
238000006407 Bischler-Napieralski reaction Methods 0.000 description 1
HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
240000003183 Manihot esculenta Species 0.000 description 1
235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
244000000231 Sesamum indicum Species 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
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150000004781 alginic acids Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000004067 bulking agent Substances 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
NUIWRMGOBPOIOY-UHFFFAOYSA-N ethanesulfonic acid;methanesulfonic acid Chemical compound CS(O)(=O)=O.CCS(O)(=O)=O NUIWRMGOBPOIOY-UHFFFAOYSA-N 0.000 description 1
239000000945 filler Substances 0.000 description 1
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150000008282 halocarbons Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
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239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
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238000007918 intramuscular administration Methods 0.000 description 1
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UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
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239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
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210000002345 respiratory system Anatomy 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
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239000011780 sodium chloride Substances 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
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239000007921 spray Substances 0.000 description 1
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230000004083 survival effect Effects 0.000 description 1
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235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH1738465A 1964-12-18 1965-12-16 Verfahren zur Herstellung von 1-Phenoxymethyl-3,4-dihydroisochinolinen und ihren Säureanlagerungssalzen CH493520A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB5154564A GB1077089A (en)	1964-12-18	1964-12-18	1-substituted-3,4-dihydroisoquinolines

Publications (1)

Publication Number	Publication Date
CH493520A true CH493520A (de)	1970-07-15

Family

ID=10460432

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1738465A CH493520A (de)	1964-12-18	1965-12-16	Verfahren zur Herstellung von 1-Phenoxymethyl-3,4-dihydroisochinolinen und ihren Säureanlagerungssalzen

Country Status (11)

Country	Link
AT (2)	AT264525B (fr)
BE (1)	BE673952A (fr)
CH (1)	CH493520A (fr)
DE (1)	DE1620122A1 (fr)
DK (1)	DK114694B (fr)
ES (1)	ES320801A1 (fr)
FI (1)	FI45757C (fr)
FR (1)	FR4911M (fr)
GB (1)	GB1077089A (fr)
NL (1)	NL6516328A (fr)
SE (1)	SE342623B (fr)

1964
- 1964-12-18 GB GB5154564A patent/GB1077089A/en not_active Expired
1965
- 1965-12-15 DE DE19651620122 patent/DE1620122A1/de active Pending
- 1965-12-15 NL NL6516328A patent/NL6516328A/xx unknown
- 1965-12-16 ES ES0320801A patent/ES320801A1/es not_active Expired
- 1965-12-16 FI FI301865A patent/FI45757C/fi active
- 1965-12-16 CH CH1738465A patent/CH493520A/de not_active IP Right Cessation
- 1965-12-17 FR FR42726A patent/FR4911M/fr not_active Expired
- 1965-12-17 BE BE673952D patent/BE673952A/xx unknown
- 1965-12-17 AT AT1136665A patent/AT264525B/de active
- 1965-12-17 AT AT650867A patent/AT271478B/de active
- 1965-12-17 SE SE1642265A patent/SE342623B/xx unknown
- 1965-12-17 DK DK648165A patent/DK114694B/da unknown

Also Published As

Publication number	Publication date
AT271478B (de)	1969-06-10
ES320801A1 (es)	1967-03-01
FI45757C (fi)	1972-09-11
NL6516328A (fr)	1966-06-20
DK114694B (da)	1969-07-28
DE1620122A1 (de)	1970-04-09
AT264525B (de)	1968-09-10
FR4911M (fr)	1967-03-13
GB1077089A (en)	1967-07-26
BE673952A (fr)	1966-04-15
SE342623B (fr)	1972-02-14
FI45757B (fr)	1972-05-31

Legal Events

Date	Code	Title	Description
1974-07-31	PL	Patent ceased

Publication	Publication Date	Title
AT363096B (de)	1981-07-10	Verfahren zur herstellung von neuen phthalazinderivaten und deren salzen
EP0047923A1 (fr)	1982-03-24	Dérivés de l'isoquinoléine, leurs procédés de préparation et compositions pharmaceutiques les contenant
DD149511A5 (de)	1981-07-15	Verfahren zur herstellung von 9-aminoalkylfluorenen
AT396362B (de)	1993-08-25	5,5-dimethyl-3-phenylvinyl-1-aminoalkoxy-iminocyclohex-2-enderivate
DE2839279A1 (de)	1979-03-29	Derivate des 1,2,3,3a,8,8a-hexahydropyrrolo eckige klammer auf 2,3-b eckige klammer zu indols, verfahren zu ihrer herstellung sowie diese enthaltende arzneimittel
EP0105210A2 (fr)	1984-04-11	Dérivés de l'isoquinoléine, leur procédé de préparation compositions pharmaceutiques les contenant et leur utilisation
EP0152868A2 (fr)	1985-08-28	Dérivés d'isoxazole, procédé de préparation et médicaments contenant ces composés
CH650249A5 (de)	1985-07-15	Basische oximaether, solche enthaltende pharmazeutische praeparate und verfahren zur herstellung derselben.
DE2609437C2 (fr)	1987-10-01
CH640507A5 (en)	1984-01-13	Process for preparing novel 1-aryloxy-2-hydroxy-3-aminopropanes
DE1927759A1 (de)	1969-12-04	Neue basische Derivate des Benzoxazolin-2-ons und Verfahren zur Herstellung derselben
DE2548968A1 (de)	1977-05-12	Neue amino-benzoesaeureamide
CH493520A (de)	1970-07-15	Verfahren zur Herstellung von 1-Phenoxymethyl-3,4-dihydroisochinolinen und ihren Säureanlagerungssalzen
CH503026A (de)	1971-02-15	Verfahren zur Herstellung von Isochinolinderivaten
CH493467A (de)	1970-07-15	Verfahren zur Herstellung von Dibenzosuberenderivaten
DE2609862C2 (fr)	1987-09-24
DE2833892A1 (de)	1979-02-22	12h-dibenzo eckige klammer auf d,g eckige klammer zu eckige klammer auf 1,3,6 eckige klammer zu dioxazocinderivate, solche enthaltende arzneimittel und verfahren zur herstellung derselben
CH615153A5 (fr)	1980-01-15
DE1095283B (de)	1960-12-22	Verfahren zur Herstellung von Phenthiazinderivaten
CH516532A (de)	1971-12-15	Verfahren zur Herstellung neuer Oximäther
DD150897A5 (de)	1981-09-23	Verfahren zur herstellung von neuen pyrazolo(1,5-c)chinazolinderivaten
DE1620151B1 (de)	1971-07-15	10-Piperazino-dibenzo(a,d)cycloheptadienderivate und Verfahren zu ihrer Herstellung
DD149664A5 (de)	1981-07-22	Verfahren zur herstellung von 1,1'-biphenyl-2-yl-alkylamin-derivaten
EP0003298A2 (fr)	1979-08-08	Dérivés de 4-hydroxy-2-benzimidazoline-thione, leur procédé de préparation et compositions pharmaceutiques les contenant
DE2836062A1 (de)	1979-03-01	N-(4-pyrazolidinyl)benzamide und deren salze und sie enthaltende pharmazeutische zubereitungen