SE464301B - Foerfarande foer framstaellning av enkainid - Google Patents
Foerfarande foer framstaellning av enkainidInfo
- Publication number
- SE464301B SE464301B SE8700776A SE8700776A SE464301B SE 464301 B SE464301 B SE 464301B SE 8700776 A SE8700776 A SE 8700776A SE 8700776 A SE8700776 A SE 8700776A SE 464301 B SE464301 B SE 464301B
- Authority
- SE
- Sweden
- Prior art keywords
- methyl
- hydrochloride
- iii
- product
- acetone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 22
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 6
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 5
- PJWPNDMDCLXCOM-UHFFFAOYSA-N encainide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=CC=C1CCC1N(C)CCCC1 PJWPNDMDCLXCOM-UHFFFAOYSA-N 0.000 claims description 5
- OJIIZIWOLTYOBS-UHFFFAOYSA-N encainide hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C(=O)NC1=CC=CC=C1CCC1N(C)CCCC1 OJIIZIWOLTYOBS-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- -1 2-nitrostyrenyl Chemical group 0.000 claims description 4
- 229960004121 encainide hydrochloride Drugs 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 235000011056 potassium acetate Nutrition 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 2
- NVKBSSIKGBDAIE-UHFFFAOYSA-N S(=O)(=O)(OC)O.CC1=NC=CC=C1 Chemical compound S(=O)(=O)(OC)O.CC1=NC=CC=C1 NVKBSSIKGBDAIE-UHFFFAOYSA-N 0.000 claims description 2
- CCXFKJBMYLLRBW-UHFFFAOYSA-N 2-[2-(1-methylpiperidin-2-yl)ethyl]aniline Chemical compound CN1CCCCC1CCC1=CC=CC=C1N CCXFKJBMYLLRBW-UHFFFAOYSA-N 0.000 claims 4
- 150000004677 hydrates Chemical class 0.000 claims 3
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 229960001142 encainide Drugs 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- DGEYTDCFMQMLTH-UHFFFAOYSA-N methanol;propan-2-ol Chemical compound OC.CC(C)O DGEYTDCFMQMLTH-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 240000007509 Phytolacca dioica Species 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QHMBFTJYGBDTHQ-UHFFFAOYSA-N n-phenylbenzamide;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 QHMBFTJYGBDTHQ-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/02—Preparation by ring-closure or hydrogenation
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/833,295 US4675409A (en) | 1986-02-25 | 1986-02-25 | Process for the preparation of encainide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8700776D0 SE8700776D0 (sv) | 1987-02-24 |
| SE8700776L SE8700776L (sv) | 1987-08-26 |
| SE464301B true SE464301B (sv) | 1991-04-08 |
Family
ID=25264016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8700776A SE464301B (sv) | 1986-02-25 | 1987-02-24 | Foerfarande foer framstaellning av enkainid |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4675409A (cs) |
| JP (1) | JPS62240659A (cs) |
| KR (1) | KR900001203B1 (cs) |
| AT (1) | AT394716B (cs) |
| AU (1) | AU597939B2 (cs) |
| BE (1) | BE1000112A5 (cs) |
| CA (1) | CA1291483C (cs) |
| CH (1) | CH671223A5 (cs) |
| DE (1) | DE3705664A1 (cs) |
| DK (1) | DK94487A (cs) |
| ES (2) | ES2002637A6 (cs) |
| FI (1) | FI85853C (cs) |
| FR (1) | FR2595353B1 (cs) |
| GB (1) | GB2187189B (cs) |
| GR (1) | GR870281B (cs) |
| HU (1) | HU196960B (cs) |
| IL (1) | IL81657A0 (cs) |
| IT (1) | IT1203501B (cs) |
| LU (1) | LU86785A1 (cs) |
| NL (1) | NL8700452A (cs) |
| PT (1) | PT84348B (cs) |
| SE (1) | SE464301B (cs) |
| ZA (1) | ZA871334B (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4800226A (en) * | 1986-02-25 | 1989-01-24 | Bristol-Myers Company | Process intermediate for the preparation of encainide |
| EP1994001A2 (en) * | 2005-11-17 | 2008-11-26 | Novartis AG | Benzeneszkfibate salts and their use as intermediates for the synthesis of 2-[2-(1-alkyl-2-piperidyl)ethyl] cinnamanilides |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA961038A (en) * | 1971-03-03 | 1975-01-14 | Joseph L. Minielli | Substituted piperidines |
| US3931195A (en) * | 1971-03-03 | 1976-01-06 | Mead Johnson & Company | Substituted piperidines |
| US4000143A (en) * | 1971-03-03 | 1976-12-28 | Mead Johnson & Company | Substituted piperidines |
| US4064254A (en) * | 1971-03-03 | 1977-12-20 | Mead Johnson & Company | Substituted piperidines therapeutic process and compositions |
| US4394507A (en) * | 1981-12-14 | 1983-07-19 | Mead Johnson & Company | Process for production of encainide |
-
1986
- 1986-02-25 US US06/833,295 patent/US4675409A/en not_active Expired - Fee Related
-
1987
- 1987-02-19 GB GB8703882A patent/GB2187189B/en not_active Expired - Fee Related
- 1987-02-20 GR GR870281A patent/GR870281B/el unknown
- 1987-02-21 DE DE19873705664 patent/DE3705664A1/de active Granted
- 1987-02-23 CA CA000530387A patent/CA1291483C/en not_active Expired - Fee Related
- 1987-02-23 FI FI870767A patent/FI85853C/fi not_active IP Right Cessation
- 1987-02-24 BE BE8700171A patent/BE1000112A5/fr not_active IP Right Cessation
- 1987-02-24 JP JP62039320A patent/JPS62240659A/ja active Pending
- 1987-02-24 IT IT19475/87A patent/IT1203501B/it active
- 1987-02-24 IL IL81657A patent/IL81657A0/xx not_active IP Right Cessation
- 1987-02-24 FR FR878702406A patent/FR2595353B1/fr not_active Expired - Fee Related
- 1987-02-24 PT PT84348A patent/PT84348B/pt not_active IP Right Cessation
- 1987-02-24 KR KR1019870001563A patent/KR900001203B1/ko not_active Expired
- 1987-02-24 DK DK094487A patent/DK94487A/da not_active Application Discontinuation
- 1987-02-24 ES ES8700482A patent/ES2002637A6/es not_active Expired
- 1987-02-24 ZA ZA871334A patent/ZA871334B/xx unknown
- 1987-02-24 NL NL8700452A patent/NL8700452A/nl not_active Application Discontinuation
- 1987-02-24 SE SE8700776A patent/SE464301B/sv not_active IP Right Cessation
- 1987-02-24 LU LU86785A patent/LU86785A1/fr unknown
- 1987-02-24 CH CH693/87A patent/CH671223A5/de not_active IP Right Cessation
- 1987-02-25 HU HU87722A patent/HU196960B/hu not_active IP Right Cessation
- 1987-02-25 AT AT0041287A patent/AT394716B/de not_active IP Right Cessation
- 1987-02-25 AU AU69246/87A patent/AU597939B2/en not_active Ceased
- 1987-06-24 ES ES8701848A patent/ES2007062A6/es not_active Expired
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HU214054B (en) | Novel process for preparing formoterol and it's n-alkyl-derivatives | |
| FI89906C (fi) | Foerfarande foer framstaellning av aminocyanacetamid | |
| US4595765A (en) | Process for preparing 5,6-dihydroxyindole | |
| US5371237A (en) | Process for the production of 4-hydroxy-2-oxopyrrolidin-1-yl-acetamide | |
| Bowman et al. | Regioselective synthesis of N-alkyl pyridones | |
| US6225473B1 (en) | Method for producing (−)cis-3-hydroxy-1-methyl-4-(2,4,6-trimethoxyphenyl)-piperidine | |
| SE464301B (sv) | Foerfarande foer framstaellning av enkainid | |
| US5744648A (en) | Process for the manufacture of 1, 3-cyclohexanedione | |
| Neumeyer et al. | Chemistry of aporphines. IV. Synthesis of aporphines via Reissert alkylation, photochemical cyclization, and the Pschorr cyclization route | |
| US4800226A (en) | Process intermediate for the preparation of encainide | |
| CN117447387A (zh) | 一种利特昔替尼关键中间体的制备方法 | |
| EP1464638A1 (en) | Process for producing erythro-3-amino-2-hydroxybutyric acid derivatives | |
| US3952010A (en) | Catalytic dehydrogenation process for the preparation of 3,5-disubstituted pyrazoles | |
| US3017427A (en) | 4-amino-2-sulfamylbenzoic acid esters | |
| US3391143A (en) | 9-piperidyl and 9-piperidylidene derivatives of acridan | |
| EP0058071A2 (en) | Process and intermediates for preparing pirbuterol | |
| Walker et al. | New Benzomorphan Ring Closure in the Synthesis of 5-Phenylbenzomorphans | |
| Yasuda et al. | Base-catalyzed reactions of. alpha.-cyano-. beta.-furylacrylic esters | |
| Constable et al. | A new synthesis of 1-alkyl (aryl)-4-isoquinolinols | |
| JP2820429B2 (ja) | ３―（３，４，５，６―テトラヒドロフタルイミド）―ベンズアルデヒドの製法 | |
| EP0251547A2 (en) | Chiral synthesis of (+)-trans-la-2,3,4A, 5,6-hexahydro-9-hydroxy-4-propyl-4H-naphth-(1,2-B)-1,4-oxazine | |
| CN108484455B (zh) | 一种合成手性光学纯对甲苯亚磺酰胺的方法 | |
| US4376860A (en) | Pyridyl ketone | |
| SU487484A3 (ru) | Способ получени производных 1-фенокси3-аминопропан-2-ола | |
| Depreux et al. | An improved synthesis of α, β methylenic cyclic ketones |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
Ref document number: 8700776-1 Effective date: 19940910 Format of ref document f/p: F |