FI60866C - Foerfarande foer framstaellning av 4-oxo-1,2,3,6,7,11b-hexahydro-4h-pyrazino-(2,1-a)isokinoliner vilka aer mellanprodukter vid framstaellning av 2-acyl-4-oxo-1,2,3,6,7,11b-hexahydro-4h-pyrazino(2,1-a)isokinoliner anvaendbara saosom antihelmintika - Google Patents
Foerfarande foer framstaellning av 4-oxo-1,2,3,6,7,11b-hexahydro-4h-pyrazino-(2,1-a)isokinoliner vilka aer mellanprodukter vid framstaellning av 2-acyl-4-oxo-1,2,3,6,7,11b-hexahydro-4h-pyrazino(2,1-a)isokinoliner anvaendbara saosom antihelmintika Download PDFInfo
- Publication number
- FI60866C FI60866C FI760519A FI760519A FI60866C FI 60866 C FI60866 C FI 60866C FI 760519 A FI760519 A FI 760519A FI 760519 A FI760519 A FI 760519A FI 60866 C FI60866 C FI 60866C
- Authority
- FI
- Finland
- Prior art keywords
- oxo
- hexahydro
- pyrazino
- isoquinoline
- acid
- Prior art date
Links
- GTRDOUXISKJZGL-UHFFFAOYSA-N 1,2,3,6,7,11b-hexahydropyrazino[2,1-a]isoquinolin-4-one Chemical compound C1=CC=C2C3CNCC(=O)N3CCC2=C1 GTRDOUXISKJZGL-UHFFFAOYSA-N 0.000 title 1
- 238000005057 refrigeration Methods 0.000 title 1
- 239000002253 acid Substances 0.000 claims description 23
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- 239000000543 intermediate Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 150000002537 isoquinolines Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 230000000507 anthelmentic effect Effects 0.000 claims description 3
- 229940124339 anthelmintic agent Drugs 0.000 claims description 3
- 239000000921 anthelmintic agent Substances 0.000 claims description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 claims 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 56
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 20
- -1 1-aminomethyl group Chemical class 0.000 description 12
- 235000011007 phosphoric acid Nutrition 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L sodium sulphate Substances [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 238000005984 hydrogenation reaction Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000002026 chloroform extract Substances 0.000 description 3
- 150000003951 lactams Chemical group 0.000 description 3
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- IOEPOEDBBPRAEI-UHFFFAOYSA-N 1,2-Dihydroisoquinoline Natural products C1=CC=C2CNC=CC2=C1 IOEPOEDBBPRAEI-UHFFFAOYSA-N 0.000 description 1
- CJWDCOSZJPAVOA-UHFFFAOYSA-N 2-acetyl-1h-isoquinoline-1-carbonitrile Chemical compound C1=CC=C2C(C#N)N(C(=O)C)C=CC2=C1 CJWDCOSZJPAVOA-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 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
- 239000004471 Glycine Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical class [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 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
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001153 fluoro group Chemical class F* 0.000 description 1
- 235000015244 frankfurter Nutrition 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910052744 lithium Chemical class 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Chemical class 0.000 description 1
- 239000001120 potassium sulphate Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- PVGBHEUCHKGFQP-UHFFFAOYSA-N sodium;n-[5-amino-2-(4-aminophenyl)sulfonylphenyl]sulfonylacetamide Chemical compound [Na+].CC(=O)NS(=O)(=O)C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 PVGBHEUCHKGFQP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000010626 work up procedure Methods 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2508947 | 1975-03-01 | ||
| DE2508947A DE2508947C3 (de) | 1975-03-01 | 1975-03-01 | Verfahren zur Herstellung von 4-Oxo-1,2,3,6,7, 11b-hexahydro-4H-pyrazino [2,1-a] isochinolinen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI760519A7 FI760519A7 (cs) | 1976-09-02 |
| FI60866B FI60866B (fi) | 1981-12-31 |
| FI60866C true FI60866C (fi) | 1982-04-13 |
Family
ID=5940184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI760519A FI60866C (fi) | 1975-03-01 | 1976-02-27 | Foerfarande foer framstaellning av 4-oxo-1,2,3,6,7,11b-hexahydro-4h-pyrazino-(2,1-a)isokinoliner vilka aer mellanprodukter vid framstaellning av 2-acyl-4-oxo-1,2,3,6,7,11b-hexahydro-4h-pyrazino(2,1-a)isokinoliner anvaendbara saosom antihelmintika |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4049659A (cs) |
| JP (1) | JPS5940155B2 (cs) |
| AT (1) | AT358043B (cs) |
| BE (1) | BE839004A (cs) |
| CA (1) | CA1068701A (cs) |
| CH (1) | CH602727A5 (cs) |
| CS (1) | CS194236B2 (cs) |
| DE (1) | DE2508947C3 (cs) |
| DK (1) | DK137275C (cs) |
| ES (1) | ES445591A1 (cs) |
| FI (1) | FI60866C (cs) |
| FR (1) | FR2303014A1 (cs) |
| GB (1) | GB1495236A (cs) |
| HU (1) | HU175127B (cs) |
| IE (1) | IE42959B1 (cs) |
| LU (1) | LU74448A1 (cs) |
| NL (1) | NL186696C (cs) |
| SE (1) | SE422579B (cs) |
| YU (1) | YU50576A (cs) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4113867A (en) * | 1973-12-17 | 1978-09-12 | Merck Patent Gesellschaft Mit Beschrankter Haftung | 2-acyl-4-oxo-pyrazino-isoquinoline derivatives and process for the preparation thereof |
| US4196291A (en) * | 1973-12-17 | 1980-04-01 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | 2-Acyl-4-oxo-pyrazino-isoquinoline derivatives and process for the preparation thereof |
| US4162319A (en) * | 1974-08-28 | 1979-07-24 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Ring substituted pyrazino-isoquinoline derivatives and their preparation |
| DE3916549C1 (cs) * | 1989-05-20 | 1990-05-17 | Daimler-Benz Aktiengesellschaft, 7000 Stuttgart, De | |
| CN100503582C (zh) * | 2005-03-01 | 2009-06-24 | 江苏工业学院 | 吡喹酮合成工艺 |
| CN101691367B (zh) * | 2009-08-31 | 2013-07-24 | 中国人民解放军第二军医大学 | 具有抗真菌活性的哌嗪并[2,1-a]异喹啉类化合物或其盐类 |
| EP2651225A4 (en) | 2010-12-13 | 2016-07-06 | Sequent Scient Ltd | PROCESS FOR PREPARING PRAZIQUANTEL |
| RU2671202C1 (ru) | 2015-02-12 | 2018-10-30 | Чжэцзян Хисун Фармасьютикал Ко., Лтд. | Способ получения празиквантела и его промежуточных соединений |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2331713A1 (de) * | 1973-06-22 | 1975-01-23 | Merck Patent Gmbh | Pyrazinoisochinolin-derivat |
-
1975
- 1975-03-01 DE DE2508947A patent/DE2508947C3/de not_active Expired
-
1976
- 1976-02-23 CS CS761180A patent/CS194236B2/cs unknown
- 1976-02-25 FR FR7605247A patent/FR2303014A1/fr active Granted
- 1976-02-25 DK DK79476A patent/DK137275C/da active
- 1976-02-26 SE SE7602535A patent/SE422579B/xx not_active IP Right Cessation
- 1976-02-27 BE BE164697A patent/BE839004A/xx not_active IP Right Cessation
- 1976-02-27 AT AT147576A patent/AT358043B/de not_active IP Right Cessation
- 1976-02-27 GB GB7831/76A patent/GB1495236A/en not_active Expired
- 1976-02-27 IE IE398/76A patent/IE42959B1/en unknown
- 1976-02-27 CA CA246,703A patent/CA1068701A/en not_active Expired
- 1976-02-27 ES ES445591A patent/ES445591A1/es not_active Expired
- 1976-02-27 LU LU74448A patent/LU74448A1/xx unknown
- 1976-02-27 JP JP51022039A patent/JPS5940155B2/ja not_active Expired
- 1976-02-27 FI FI760519A patent/FI60866C/fi not_active IP Right Cessation
- 1976-02-27 YU YU00505/76A patent/YU50576A/xx unknown
- 1976-02-27 US US05/662,009 patent/US4049659A/en not_active Expired - Lifetime
- 1976-03-01 HU HU76ME1959A patent/HU175127B/hu unknown
- 1976-03-01 CH CH251576A patent/CH602727A5/xx not_active IP Right Cessation
- 1976-03-01 NL NLAANVRAGE7602101,A patent/NL186696C/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CS194236B2 (en) | 1979-11-30 |
| CH602727A5 (cs) | 1978-07-31 |
| ATA147576A (de) | 1980-01-15 |
| DK137275B (da) | 1978-02-13 |
| DE2508947B2 (de) | 1981-05-07 |
| FR2303014B1 (cs) | 1978-05-19 |
| ES445591A1 (es) | 1977-06-01 |
| JPS51110600A (en) | 1976-09-30 |
| YU50576A (en) | 1982-05-31 |
| CA1068701A (en) | 1979-12-25 |
| BE839004A (fr) | 1976-08-27 |
| NL7602101A (nl) | 1976-09-03 |
| HU175127B (hu) | 1980-05-28 |
| DE2508947A1 (de) | 1976-09-09 |
| LU74448A1 (cs) | 1977-09-12 |
| DE2508947C3 (de) | 1982-02-25 |
| NL186696B (nl) | 1990-09-03 |
| IE42959L (en) | 1976-09-01 |
| FR2303014A1 (fr) | 1976-10-01 |
| US4049659A (en) | 1977-09-20 |
| FI760519A7 (cs) | 1976-09-02 |
| DK137275C (da) | 1978-07-17 |
| AT358043B (de) | 1980-08-11 |
| SE422579B (sv) | 1982-03-15 |
| IE42959B1 (en) | 1980-11-19 |
| NL186696C (nl) | 1991-02-01 |
| FI60866B (fi) | 1981-12-31 |
| SE7602535L (sv) | 1976-09-02 |
| JPS5940155B2 (ja) | 1984-09-28 |
| DK79476A (da) | 1976-09-02 |
| GB1495236A (en) | 1977-12-14 |
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