CH629782A5 - Verfahren zur herstellung von 4-hydroxy-aporphinderivaten. - Google Patents
Verfahren zur herstellung von 4-hydroxy-aporphinderivaten. Download PDFInfo
- Publication number
- CH629782A5 CH629782A5 CH691177A CH691177A CH629782A5 CH 629782 A5 CH629782 A5 CH 629782A5 CH 691177 A CH691177 A CH 691177A CH 691177 A CH691177 A CH 691177A CH 629782 A5 CH629782 A5 CH 629782A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- solution
- trifluoroacetic acid
- temperature
- vanadyl
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 60
- HHQFLEDKAVLHOM-UHFFFAOYSA-N oxovanadium;trihydrofluoride Chemical compound F.F.F.[V]=O HHQFLEDKAVLHOM-UHFFFAOYSA-N 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 3
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- 230000008018 melting Effects 0.000 description 3
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- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
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- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
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- 239000000463 material Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 238000005691 oxidative coupling reaction Methods 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229960001789 papaverine Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 229940095064 tartrate Drugs 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
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/18—Ring systems of four or more rings
-
- 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
- A61P9/12—Antihypertensives
-
- 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
- C07D217/18—Aralkyl radicals
- C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2625116A DE2625116C2 (de) | 1976-06-04 | 1976-06-04 | Verfahren zur Herstellung von 4-Hydroxy-aporphin-Derivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH629782A5 true CH629782A5 (de) | 1982-05-14 |
Family
ID=5979808
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH691177A CH629782A5 (de) | 1976-06-04 | 1977-06-03 | Verfahren zur herstellung von 4-hydroxy-aporphinderivaten. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4120964A (enExample) |
| JP (1) | JPS535169A (enExample) |
| AU (1) | AU508171B2 (enExample) |
| BE (1) | BE855412A (enExample) |
| CH (1) | CH629782A5 (enExample) |
| DE (1) | DE2625116C2 (enExample) |
| DK (1) | DK248277A (enExample) |
| ES (1) | ES459504A1 (enExample) |
| FR (1) | FR2353534A1 (enExample) |
| GB (1) | GB1521020A (enExample) |
| IE (1) | IE44937B1 (enExample) |
| LU (1) | LU77482A1 (enExample) |
| NL (1) | NL7706180A (enExample) |
| SE (1) | SE433212B (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2757335C3 (de) * | 1977-12-22 | 1982-03-25 | Gödecke AG, 1000 Berlin | Verfahren zur O-Methylierung von Hydroxyaporphinen |
| DE2757281C3 (de) * | 1977-12-22 | 1980-10-23 | Goedecke Ag, 1000 Berlin | Verfahren zur Herstellung von 1 -Hydroxy-Aporphinderivaten |
| FI68813C (fi) * | 1978-08-21 | 1985-11-11 | Dow Chemical Co | Foerfarande foer framstaellning av terapeutiskt effektiva 1- och d,1-glausinfosfatsalter |
| DE3324089A1 (de) * | 1983-07-05 | 1985-01-17 | Basf Ag, 6700 Ludwigshafen | Elektrophotographische aufzeichnungsmaterialien mit verbesserter photoempfindlichkeit |
| DE3324090A1 (de) * | 1983-07-05 | 1985-01-17 | Basf Ag, 6700 Ludwigshafen | Elektrophotographische aufzeichnungsmaterialien mit verbesserter photoempfindlichkeit |
| US5156847A (en) * | 1990-09-20 | 1992-10-20 | Walter H. Lewis | Wound-healing composition |
| US5474782A (en) * | 1994-05-20 | 1995-12-12 | Woundfast Pharmaceuticals, Inc. | Wound-healing composition and method |
| US5659037A (en) * | 1994-08-18 | 1997-08-19 | Abbott Laboratories | Process for preparing chiral tetracyclic dopaminergic compounds |
| DE19535762A1 (de) * | 1995-09-26 | 1997-03-27 | Basf Ag | Verfahren zur Racematspaltung |
| US5932617A (en) * | 1998-02-06 | 1999-08-03 | Woundfast Pharmaceuticals Inc. | Wound-treating composition and method |
| US6210680B1 (en) | 1999-06-11 | 2001-04-03 | Univera Pharmaceuticals, Inc. | Method for the prevention and treatment of chronic venous insufficiency |
| US20030187011A1 (en) * | 2001-12-20 | 2003-10-02 | Lashuel Hilal A. | Apomorphine inhibitors of amyloid-beta (Abeta) fibril formation and their use in amyloidosis based disease |
| TWI404536B (zh) * | 2008-06-20 | 2013-08-11 | Standard Chem & Pharm Co Ltd | 阿朴芬化合物及其醫藥用途 |
| CN105315208A (zh) * | 2014-07-17 | 2016-02-10 | 中国科学院兰州化学物理研究所 | 阿朴菲类生物碱及其制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3131191A (en) * | 1962-08-08 | 1964-04-28 | Smith Kline French Lab | Process for the preparation of noraporphines |
-
1976
- 1976-06-04 DE DE2625116A patent/DE2625116C2/de not_active Expired
-
1977
- 1977-05-25 US US05/800,492 patent/US4120964A/en not_active Expired - Lifetime
- 1977-05-30 IE IE1110/77A patent/IE44937B1/en unknown
- 1977-06-01 GB GB23115/77A patent/GB1521020A/en not_active Expired
- 1977-06-03 BE BE6046041A patent/BE855412A/xx not_active IP Right Cessation
- 1977-06-03 FR FR7716976A patent/FR2353534A1/fr active Granted
- 1977-06-03 SE SE7706488A patent/SE433212B/xx unknown
- 1977-06-03 JP JP6561677A patent/JPS535169A/ja active Pending
- 1977-06-03 LU LU77482A patent/LU77482A1/xx unknown
- 1977-06-03 CH CH691177A patent/CH629782A5/de not_active IP Right Cessation
- 1977-06-03 AU AU25809/77A patent/AU508171B2/en not_active Expired
- 1977-06-03 DK DK248277A patent/DK248277A/da not_active Application Discontinuation
- 1977-06-03 NL NL7706180A patent/NL7706180A/xx not_active Application Discontinuation
- 1977-06-04 ES ES459504A patent/ES459504A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK248277A (da) | 1977-12-05 |
| IE44937L (en) | 1977-12-04 |
| JPS535169A (en) | 1978-01-18 |
| FR2353534B1 (enExample) | 1980-03-07 |
| BE855412A (fr) | 1977-12-05 |
| AU508171B2 (en) | 1980-03-13 |
| IE44937B1 (en) | 1982-05-19 |
| LU77482A1 (enExample) | 1977-09-22 |
| FR2353534A1 (fr) | 1977-12-30 |
| SE433212B (sv) | 1984-05-14 |
| ES459504A1 (es) | 1978-05-01 |
| DE2625116C2 (de) | 1984-01-26 |
| GB1521020A (en) | 1978-08-09 |
| AU2580977A (en) | 1978-12-07 |
| DE2625116A1 (de) | 1977-12-22 |
| US4120964A (en) | 1978-10-17 |
| SE7706488L (sv) | 1977-12-05 |
| NL7706180A (nl) | 1977-12-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |