AT287720B - Verfahren zur Herstellung von neuen 1-(2-Pyridyl)-1,2,3,4-tetrahydro-isochinolinen sowie deren Säureadditionssalzen - Google Patents
Verfahren zur Herstellung von neuen 1-(2-Pyridyl)-1,2,3,4-tetrahydro-isochinolinen sowie deren SäureadditionssalzenInfo
- Publication number
- AT287720B AT287720B AT197369A AT197369A AT287720B AT 287720 B AT287720 B AT 287720B AT 197369 A AT197369 A AT 197369A AT 197369 A AT197369 A AT 197369A AT 287720 B AT287720 B AT 287720B
- Authority
- AT
- Austria
- Prior art keywords
- formula
- formic acid
- compounds
- pyridyl
- isoquinoline
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 239000002253 acid Substances 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 6
- 150000003839 salts Chemical class 0.000 title claims description 6
- XYYUSMIOLBNTRM-UHFFFAOYSA-N 1-pyridin-2-yl-1,2,3,4-tetrahydroisoquinoline Chemical class N1CCC2=CC=CC=C2C1C1=CC=CC=N1 XYYUSMIOLBNTRM-UHFFFAOYSA-N 0.000 title claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 16
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- 235000019253 formic acid Nutrition 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- -1 alkyl radicals Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229920002866 paraformaldehyde Polymers 0.000 claims description 5
- IOEPOEDBBPRAEI-UHFFFAOYSA-N 1,2-dihydroisoquinoline Chemical compound C1=CC=C2CNC=CC2=C1 IOEPOEDBBPRAEI-UHFFFAOYSA-N 0.000 claims description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 230000009467 reduction Effects 0.000 claims description 4
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000004678 hydrides Chemical class 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 235000021190 leftovers Nutrition 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 239000007868 Raney catalyst Substances 0.000 description 5
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 5
- 229910000564 Raney nickel Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- QTEZWJVHWHCJDX-UHFFFAOYSA-N 3,3-dimethyl-1-pyridin-2-yl-4h-isoquinoline Chemical compound N=1C(C)(C)CC2=CC=CC=C2C=1C1=CC=CC=N1 QTEZWJVHWHCJDX-UHFFFAOYSA-N 0.000 description 4
- TWWIYQSAWIJWJH-UHFFFAOYSA-N CC1(NC(C2=CC=CC=C2C1)C1=NC=CC=C1)C Chemical compound CC1(NC(C2=CC=CC=C2C1)C1=NC=CC=C1)C TWWIYQSAWIJWJH-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 4
- 229960002456 hexobarbital Drugs 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- XLLQXMOAAIZTQI-UHFFFAOYSA-N CC1(C)CC2=C(C=CC=C2)C(N1C=O)C1=NC=CC=C1 Chemical compound CC1(C)CC2=C(C=CC=C2)C(N1C=O)C1=NC=CC=C1 XLLQXMOAAIZTQI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000012448 Lithium borohydride Substances 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000004904 shortening Methods 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 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
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- GKPITGQPHJASLZ-UHFFFAOYSA-N 3,3-diethyl-1-pyridin-2-yl-2,4-dihydro-1H-isoquinoline Chemical compound C(C)C1(NC(C2=CC=CC=C2C1)C1=NC=CC=C1)CC GKPITGQPHJASLZ-UHFFFAOYSA-N 0.000 description 1
- GZZUSVCHJDRMKF-UHFFFAOYSA-N 3,3-diethyl-1-pyridin-2-yl-4H-isoquinoline Chemical compound C(C)C1(N=C(C2=CC=CC=C2C1)C1=NC=CC=C1)CC GZZUSVCHJDRMKF-UHFFFAOYSA-N 0.000 description 1
- VFRKELRWEUAIKF-UHFFFAOYSA-N 3,3-dimethyl-1-(6-methylpyridin-2-yl)-2,4-dihydro-1H-isoquinoline Chemical compound CC1(NC(C2=CC=CC=C2C1)C1=NC(=CC=C1)C)C VFRKELRWEUAIKF-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
- 229910000497 Amalgam Inorganic materials 0.000 description 1
- RGLPGKQDJZXCQQ-UHFFFAOYSA-N CC1(N=C(C2=CC=CC=C2C1C)C1=NC=CC=C1)C Chemical compound CC1(N=C(C2=CC=CC=C2C1C)C1=NC=CC=C1)C RGLPGKQDJZXCQQ-UHFFFAOYSA-N 0.000 description 1
- LDXFQQNGUFMPSY-UHFFFAOYSA-N CC1(NC(C2=CC=CC=C2C1C)C1=NC=CC=C1)C Chemical compound CC1(NC(C2=CC=CC=C2C1C)C1=NC=CC=C1)C LDXFQQNGUFMPSY-UHFFFAOYSA-N 0.000 description 1
- NRJGKXPTQYUJSR-UHFFFAOYSA-N CCC1(CC)CC2=C(C=CC=C2)C(N1C)C1=NC=CC=C1 Chemical compound CCC1(CC)CC2=C(C=CC=C2)C(N1C)C1=NC=CC=C1 NRJGKXPTQYUJSR-UHFFFAOYSA-N 0.000 description 1
- IKYKREGBBSHGGH-UHFFFAOYSA-N Cl.C(C)C1(N(C(C2=CC=CC=C2C1)C1=NC=CC=C1)C=O)CC Chemical compound Cl.C(C)C1(N(C(C2=CC=CC=C2C1)C1=NC=CC=C1)C=O)CC IKYKREGBBSHGGH-UHFFFAOYSA-N 0.000 description 1
- UHABRCBNUPTFNC-UHFFFAOYSA-N Cl.CC1(C)CC2=CC=CC=C2C(=N1)C1=NC=CC=C1 Chemical compound Cl.CC1(C)CC2=CC=CC=C2C(=N1)C1=NC=CC=C1 UHABRCBNUPTFNC-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 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
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 210000004185 liver Anatomy 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000009666 routine test Methods 0.000 description 1
- 230000004622 sleep time Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- FBGKGORFGWHADY-UHFFFAOYSA-L tin(2+);dihydroxide Chemical compound O[Sn]O FBGKGORFGWHADY-UHFFFAOYSA-L 0.000 description 1
- 229910021509 tin(II) hydroxide Inorganic materials 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681695922 DE1695922A1 (de) | 1968-02-27 | 1968-02-27 | Verfahren zur Herstellung von 1-(2-Pyridyl)-1,2,3,4-tetrahydro-isochinolinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT287720B true AT287720B (de) | 1971-02-10 |
Family
ID=5687905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT197369A AT287720B (de) | 1968-02-27 | 1969-02-27 | Verfahren zur Herstellung von neuen 1-(2-Pyridyl)-1,2,3,4-tetrahydro-isochinolinen sowie deren Säureadditionssalzen |
Country Status (2)
| Country | Link |
|---|---|
| JP (2) | JPS4823439B1 (enExample) |
| AT (1) | AT287720B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52107030U (enExample) * | 1976-02-12 | 1977-08-15 |
-
1969
- 1969-02-27 AT AT197369A patent/AT287720B/de not_active IP Right Cessation
-
1970
- 1970-01-07 JP JP218870A patent/JPS4823439B1/ja active Pending
- 1970-01-07 JP JP218770A patent/JPS4823438B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4823438B1 (enExample) | 1973-07-13 |
| JPS4823439B1 (enExample) | 1973-07-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ELJ | Ceased due to non-payment of the annual fee |