DD145532A5 - Verfahren zur herstellung von 7,8-dichlor-1,2,3,4-tetrahydroisochinolin - Google Patents
Verfahren zur herstellung von 7,8-dichlor-1,2,3,4-tetrahydroisochinolin Download PDFInfo
- Publication number
- DD145532A5 DD145532A5 DD79214893A DD21489379A DD145532A5 DD 145532 A5 DD145532 A5 DD 145532A5 DD 79214893 A DD79214893 A DD 79214893A DD 21489379 A DD21489379 A DD 21489379A DD 145532 A5 DD145532 A5 DD 145532A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- chloride
- reaction
- aluminum chloride
- mmol
- item
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 50
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 12
- 235000019270 ammonium chloride Nutrition 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- -1 ammonium halides Chemical class 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
- 239000012433 hydrogen halide Substances 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- LVCDXCQFSONNDO-UHFFFAOYSA-N n-benzylhydroxylamine Chemical compound ONCC1=CC=CC=C1 LVCDXCQFSONNDO-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 235000002639 sodium chloride Nutrition 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000000460 chlorine Chemical group 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Chemical group 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- GQCJTRZKCFBVQK-UHFFFAOYSA-N 2-[(2,3-dichlorophenyl)methylamino]ethanol Chemical compound OCCNCC1=CC=CC(Cl)=C1Cl GQCJTRZKCFBVQK-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000001030 gas--liquid chromatography Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical class C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
- LLMLNAVBOAMOEE-UHFFFAOYSA-N 2,3-dichlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1Cl LLMLNAVBOAMOEE-UHFFFAOYSA-N 0.000 description 2
- SUKDCMQPGWYAEJ-UHFFFAOYSA-N 2-[(2,3-dichlorophenyl)methylamino]ethanol;hydrochloride Chemical compound Cl.OCCNCC1=CC=CC(Cl)=C1Cl SUKDCMQPGWYAEJ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 108010002822 Phenylethanolamine N-Methyltransferase Proteins 0.000 description 2
- 102100028917 Phenylethanolamine N-methyltransferase Human genes 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 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
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- KEYKSFAHECWVRQ-UHFFFAOYSA-N 2-[(2,3-dichlorophenyl)methylamino]ethanol;hydrobromide Chemical compound Br.OCCNCC1=CC=CC(Cl)=C1Cl KEYKSFAHECWVRQ-UHFFFAOYSA-N 0.000 description 1
- MSROIXVDNRYFFA-UHFFFAOYSA-N 2-chloro-n-[(2,3-dichlorophenyl)methyl]ethanamine;hydrochloride Chemical compound Cl.ClCCNCC1=CC=CC(Cl)=C1Cl MSROIXVDNRYFFA-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
- MPGYNUDLCXDURR-UHFFFAOYSA-N 7,8-dichloro-1,2,3,4-tetrahydroisoquinolin-2-ium;chloride Chemical compound Cl.C1CNCC2=C(Cl)C(Cl)=CC=C21 MPGYNUDLCXDURR-UHFFFAOYSA-N 0.000 description 1
- WFPUBEDBBOGGIQ-UHFFFAOYSA-N 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline Chemical compound C1CNCC2=C(Cl)C(Cl)=CC=C21 WFPUBEDBBOGGIQ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 101100453960 Drosophila melanogaster klar gene Proteins 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical group NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
- 150000003939 benzylamines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000003840 hydrochlorides Chemical group 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002537 isoquinolines Chemical class 0.000 description 1
- 239000007788 liquid Substances 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- C07D217/02—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/932,586 US4251660A (en) | 1978-08-10 | 1978-08-10 | Method for preparing tetrahydroisoquinolines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD145532A5 true DD145532A5 (de) | 1980-12-17 |
Family
ID=25462546
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79214893A DD145532A5 (de) | 1978-08-10 | 1979-08-09 | Verfahren zur herstellung von 7,8-dichlor-1,2,3,4-tetrahydroisochinolin |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US4251660A (cs) |
| EP (1) | EP0008405B1 (cs) |
| JP (1) | JPS5524196A (cs) |
| AR (1) | AR220218A1 (cs) |
| AT (1) | ATE258T1 (cs) |
| AU (1) | AU522843B2 (cs) |
| BG (1) | BG32714A3 (cs) |
| CA (1) | CA1130290A (cs) |
| CS (1) | CS226006B2 (cs) |
| DD (1) | DD145532A5 (cs) |
| DE (1) | DE2961141D1 (cs) |
| DK (1) | DK330579A (cs) |
| ES (1) | ES483151A1 (cs) |
| FI (1) | FI65062C (cs) |
| GR (1) | GR69853B (cs) |
| HU (1) | HU178110B (cs) |
| IE (1) | IE48618B1 (cs) |
| IL (1) | IL57980A (cs) |
| IN (1) | IN152421B (cs) |
| IT (1) | IT1227791B (cs) |
| MX (1) | MX5581E (cs) |
| NO (1) | NO153807C (cs) |
| NZ (1) | NZ191227A (cs) |
| PH (1) | PH24441A (cs) |
| PL (1) | PL217684A1 (cs) |
| PT (1) | PT70029A (cs) |
| RO (1) | RO78160A (cs) |
| SU (1) | SU860698A3 (cs) |
| ZA (1) | ZA793308B (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0161350A1 (en) * | 1981-11-27 | 1985-11-21 | Smithkline Beckman Corporation | Process for preparing benzazepines |
| US4541954A (en) * | 1984-09-05 | 1985-09-17 | Smithkline Beckman Corporation | Method for preparing 6-chloro-N-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2771468A (en) * | 1954-02-19 | 1956-11-20 | Sterling Drug Inc | 4-aralkyl-3-morpholones, 4-aralkyl-3-homomorpholones and their preparation |
| US3947456A (en) * | 1970-01-06 | 1976-03-30 | Hoffman-La Roche Inc. | Substituted 4-phenyl isoquinolines |
| US3752892A (en) * | 1970-03-11 | 1973-08-14 | Ciba Geigy Corp | Anorexigenic tetrahydrobenzazepine derivative method and composition thereof |
-
1978
- 1978-08-10 US US05/932,586 patent/US4251660A/en not_active Expired - Lifetime
-
1979
- 1979-06-27 IN IN470/DEL/79A patent/IN152421B/en unknown
- 1979-07-03 ZA ZA793308A patent/ZA793308B/xx unknown
- 1979-08-02 IT IT7924894A patent/IT1227791B/it active
- 1979-08-03 CA CA333,200A patent/CA1130290A/en not_active Expired
- 1979-08-03 AR AR277592A patent/AR220218A1/es active
- 1979-08-03 PH PH22859A patent/PH24441A/en unknown
- 1979-08-03 AU AU49547/79A patent/AU522843B2/en not_active Ceased
- 1979-08-06 GR GR59778A patent/GR69853B/el unknown
- 1979-08-06 ES ES483151A patent/ES483151A1/es not_active Expired
- 1979-08-06 PT PT70029A patent/PT70029A/pt unknown
- 1979-08-06 IL IL57980A patent/IL57980A/xx unknown
- 1979-08-06 FI FI792436A patent/FI65062C/fi not_active IP Right Cessation
- 1979-08-06 NZ NZ191227A patent/NZ191227A/xx unknown
- 1979-08-07 JP JP10115279A patent/JPS5524196A/ja active Pending
- 1979-08-07 DE DE7979102847T patent/DE2961141D1/de not_active Expired
- 1979-08-07 DK DK330579A patent/DK330579A/da not_active Application Discontinuation
- 1979-08-07 EP EP79102847A patent/EP0008405B1/en not_active Expired
- 1979-08-07 AT AT79102847T patent/ATE258T1/de not_active IP Right Cessation
- 1979-08-08 RO RO7998406A patent/RO78160A/ro unknown
- 1979-08-09 HU HU79SI1715A patent/HU178110B/hu unknown
- 1979-08-09 CS CS795460A patent/CS226006B2/cs unknown
- 1979-08-09 NO NO792601A patent/NO153807C/no unknown
- 1979-08-09 IE IE1534/79A patent/IE48618B1/en unknown
- 1979-08-09 DD DD79214893A patent/DD145532A5/de unknown
- 1979-08-10 BG BG044609A patent/BG32714A3/xx unknown
- 1979-08-10 MX MX798312U patent/MX5581E/es unknown
- 1979-08-10 PL PL21768479A patent/PL217684A1/xx unknown
- 1979-08-10 SU SU792798064A patent/SU860698A3/ru active
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2503815C2 (de) | Indazol-Derivate, Verfahren zu ihrer Herstellung und Arzneimittel | |
| DE1620694C3 (de) | Verfahren zur Herstellung von 5-Methyl-7-diäthylamino-s-triazolo [1,5-a] pyrimidin und seinen Salzen mit Säuren | |
| DE1795808B1 (de) | Verfahren zur Herstellung von 2,2,6,6-Tetramethyl-4-oxopiperidin | |
| DE2803651C2 (cs) | ||
| DE2632414A1 (de) | O-nitrobutyrophenone und verfahren zur herstellung von o-aminobutyrophenonen | |
| DE1543777C3 (de) | Verfahren zur Herstellung von alpha-niedrig Alkyl-beta-(4-hydroxyphenyl)-alaninen | |
| EP0608693A2 (de) | Verfahren zur Herstellung von Folsäure | |
| DD145532A5 (de) | Verfahren zur herstellung von 7,8-dichlor-1,2,3,4-tetrahydroisochinolin | |
| DE2602846C2 (de) | Verfahren zur Herstellung von 2-(2-Thienyl)äthylaminen | |
| DE1620305A1 (de) | Verfahren zur Herstellung von 3-Aminoisoxazolderivaten | |
| AT392784B (de) | Verfahren zur herstellung von derivaten der 2-thiophenessigsaeure | |
| DE2433176C3 (de) | N-Cyano-cyano-acetimidate und Verfahren zur Herstellung von 2-Halopyrinüdinderivaten | |
| DE1695549C3 (de) | Verfahren zur Herstellung von LundDL-alpha-Methyl-3,4-dihydroxyphenylalanin | |
| DE3026602A1 (de) | 14-oxo-15-halogen-e-homoeburnanderivate, verfahren zur herstellung derselben und von 14-oxo-15-hydroxyimino-e-homoeburnanderivaten und die ersteren enthaltende arzneimittel | |
| DE2058237C (cs) | ||
| DE3538747A1 (de) | Verfahren zur herstellung von pyrrolidin-derivaten | |
| DE2558399A1 (de) | Herstellung von 3,6-dichlorpicolinsaeure | |
| DE2065698A1 (de) | Verfahren zur herstellung von 2isopropyl-6-methyl-4(3h)-pyrimidon | |
| DE2023460C3 (de) | L- und DL-Tyrosine und Verfahren zu ihrer Herstellung | |
| DE2321332C2 (de) | Verfahren zur Herstellung von 2-Nitro-5-chlor-benzolsulfonsäurechlorid oder von 2-Nitro-5-chlor-benzolsulfonsäure | |
| DE2043378C3 (de) | Verfahren zur Herstellung von Lactamkomplexen | |
| AT360995B (de) | Verfahren zur herstellung neuer phenylazacyclo- alkane und von deren salzen und optisch aktiven verbindungen | |
| DE1151809B (de) | Verfahren zur Herstellung appetitzuegelnd wirkender ª‰-Phenylalkylamine | |
| DE3620667A1 (de) | Verfahren zur herstellung von 2-aminoaethansulfonamid | |
| DE2058237A1 (de) | Verfahren zur Herstellung von trans-4-Aminomethylcyclohexancarbonsaeure-(1) |