SU420173A3 - Способ получения ацилпроизводнб1х просцилларидина а - Google Patents
Способ получения ацилпроизводнб1х просцилларидина аInfo
- Publication number
- SU420173A3 SU420173A3 SU1728032A SU1728032A SU420173A3 SU 420173 A3 SU420173 A3 SU 420173A3 SU 1728032 A SU1728032 A SU 1728032A SU 1728032 A SU1728032 A SU 1728032A SU 420173 A3 SU420173 A3 SU 420173A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- proscillaridin
- ortho ester
- trimethyl
- proscillaridine
- Prior art date
Links
- MYEJFUXQJGHEQK-ALRJYLEOSA-N Proscillaridin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C=C2CC[C@H]3[C@@]4(O)CC[C@H](C5=COC(=O)C=C5)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1 MYEJFUXQJGHEQK-ALRJYLEOSA-N 0.000 title description 20
- 238000000034 method Methods 0.000 title description 6
- 150000002905 orthoesters Chemical class 0.000 description 23
- 229960003584 proscillaridin Drugs 0.000 description 19
- MYEJFUXQJGHEQK-UHFFFAOYSA-N proscillaridin A Natural products OC1C(O)C(O)C(C)OC1OC1C=C2CCC3C4(O)CCC(C5=COC(=O)C=C5)C4(C)CCC3C2(C)CC1 MYEJFUXQJGHEQK-UHFFFAOYSA-N 0.000 description 18
- -1 cycloalkyl radical Chemical group 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229930190098 proscillaridin Natural products 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YVHAIVPPUIZFBA-UHFFFAOYSA-N Cyclopentylacetic acid Chemical compound OC(=O)CC1CCCC1 YVHAIVPPUIZFBA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical compound OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 description 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 229910001923 silver oxide Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KVFQMAZOBTXCAZ-UHFFFAOYSA-N 3,4-Hexanedione Chemical group CCC(=O)C(=O)CC KVFQMAZOBTXCAZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 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
- 230000002152 alkylating effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229940097217 cardiac glycoside Drugs 0.000 description 1
- 239000002368 cardiac glycoside Substances 0.000 description 1
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- URAXDCBRCGSGAT-UHFFFAOYSA-N cyclooctanecarboxylic acid Chemical compound OC(=O)C1CCCCCCC1 URAXDCBRCGSGAT-UHFFFAOYSA-N 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- SGBIPKSFOQACNA-UHFFFAOYSA-N cyclopropanecarboxylic acid;hydrochloride Chemical compound Cl.OC(=O)C1CC1 SGBIPKSFOQACNA-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229930002534 steroid glycoside Natural products 0.000 description 1
- 150000008143 steroidal glycosides Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- QENJZWZWAWWESF-UHFFFAOYSA-N tri-methylbenzoic acid Natural products CC1=CC(C)=C(C(O)=O)C=C1C QENJZWZWAWWESF-UHFFFAOYSA-N 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/286—Polysaccharides, e.g. gums; Cyclodextrin
- A61K9/2866—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J19/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 by a lactone ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/284—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/2853—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers, poly(lactide-co-glycolide)
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2063406A DE2063406C3 (de) | 1970-12-23 | 1970-12-23 | Acylderivate des Proscillaridin A, Verfahren zu deren Herstellung und diese enthaltende Präparate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU420173A3 true SU420173A3 (ru) | 1974-03-15 |
Family
ID=5791955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1728032A SU420173A3 (ru) | 1970-12-23 | 1971-12-21 | Способ получения ацилпроизводнб1х просцилларидина а |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS5741480B1 (xx) |
| AT (1) | AT312815B (xx) |
| AU (1) | AU469336B2 (xx) |
| BE (1) | BE777164A (xx) |
| BG (1) | BG20580A3 (xx) |
| CA (1) | CA939664A (xx) |
| CH (1) | CH593302A5 (xx) |
| CS (1) | CS166041B2 (xx) |
| DD (1) | DD95231A5 (xx) |
| DE (1) | DE2063406C3 (xx) |
| DK (1) | DK129654B (xx) |
| ES (1) | ES398208A1 (xx) |
| FI (1) | FI50248C (xx) |
| FR (1) | FR2119045B1 (xx) |
| GB (1) | GB1374079A (xx) |
| HU (1) | HU162742B (xx) |
| IE (1) | IE36110B1 (xx) |
| IL (1) | IL38430A (xx) |
| NL (1) | NL7117645A (xx) |
| NO (1) | NO136671C (xx) |
| PL (1) | PL83079B1 (xx) |
| RO (1) | RO59396A (xx) |
| SE (1) | SE380812B (xx) |
| SU (1) | SU420173A3 (xx) |
| YU (1) | YU35150B (xx) |
| ZA (1) | ZA718589B (xx) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2427976C2 (de) * | 1974-06-10 | 1985-12-12 | Knoll Ag, 6700 Ludwigshafen | Proscillaridinäther, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU33975B (en) * | 1969-01-09 | 1978-09-08 | Knol Ag Chemische Fabriken | Process for preparing bufatrienolide-rhamnoside-acylates |
| DE1910207C3 (de) * | 1969-02-28 | 1978-04-13 | Knoll Ag, 6700 Ludwigshafen | Verfahren zu deren Herstellung |
| RO60624A (xx) * | 1970-03-05 | 1976-07-15 | ||
| JPS512471A (ja) * | 1974-06-25 | 1976-01-10 | Yasushi Maeda | Shootoringutokoiruno toritsukeho |
| JPS526988A (en) * | 1975-07-04 | 1977-01-19 | Sumitomo Electric Ind Ltd | Insulated wire |
-
1970
- 1970-12-23 DE DE2063406A patent/DE2063406C3/de not_active Expired
-
1971
- 1971-12-18 BG BG019278A patent/BG20580A3/xx unknown
- 1971-12-20 CH CH1859471A patent/CH593302A5/xx not_active IP Right Cessation
- 1971-12-20 JP JP46103559A patent/JPS5741480B1/ja active Pending
- 1971-12-21 HU HUBO1338A patent/HU162742B/hu unknown
- 1971-12-21 ES ES398208A patent/ES398208A1/es not_active Expired
- 1971-12-21 SU SU1728032A patent/SU420173A3/ru active
- 1971-12-22 SE SE7116530A patent/SE380812B/xx unknown
- 1971-12-22 IL IL38430A patent/IL38430A/xx unknown
- 1971-12-22 AU AU37197/71A patent/AU469336B2/en not_active Expired
- 1971-12-22 NL NL7117645A patent/NL7117645A/xx not_active Application Discontinuation
- 1971-12-22 PL PL1971152413A patent/PL83079B1/pl unknown
- 1971-12-22 BE BE777164A patent/BE777164A/xx unknown
- 1971-12-22 FI FI713661A patent/FI50248C/fi active
- 1971-12-22 AT AT1103471A patent/AT312815B/de not_active IP Right Cessation
- 1971-12-22 CS CS8920A patent/CS166041B2/cs unknown
- 1971-12-22 CA CA130,806A patent/CA939664A/en not_active Expired
- 1971-12-22 NO NO4779/71A patent/NO136671C/no unknown
- 1971-12-22 GB GB5972671A patent/GB1374079A/en not_active Expired
- 1971-12-22 DD DD159823A patent/DD95231A5/xx unknown
- 1971-12-22 ZA ZA718589A patent/ZA718589B/xx unknown
- 1971-12-22 YU YU3224/71A patent/YU35150B/xx unknown
- 1971-12-22 DK DK628671AA patent/DK129654B/da not_active IP Right Cessation
- 1971-12-22 RO RO69152A patent/RO59396A/ro unknown
- 1971-12-23 IE IE1638/71A patent/IE36110B1/xx unknown
- 1971-12-23 FR FR7146346A patent/FR2119045B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2063406A1 (de) | 1972-09-21 |
| BG20580A3 (bg) | 1975-12-05 |
| SE380812B (sv) | 1975-11-17 |
| AU469336B2 (en) | 1973-06-28 |
| DD95231A5 (xx) | 1973-01-20 |
| ZA718589B (en) | 1973-08-29 |
| CA939664A (en) | 1974-01-08 |
| IE36110B1 (en) | 1976-08-18 |
| HU162742B (xx) | 1973-04-28 |
| FI50248B (xx) | 1975-09-30 |
| IL38430A (en) | 1975-05-22 |
| DK129654B (da) | 1974-11-04 |
| FR2119045B1 (xx) | 1975-10-10 |
| ES398208A1 (es) | 1974-08-16 |
| AT312815B (de) | 1974-01-25 |
| PL83079B1 (xx) | 1975-12-31 |
| CS166041B2 (xx) | 1976-01-29 |
| AU3719771A (en) | 1973-06-28 |
| YU322471A (en) | 1980-03-15 |
| RO59396A (xx) | 1976-05-15 |
| BE777164A (fr) | 1972-06-22 |
| YU35150B (en) | 1980-09-25 |
| FR2119045A1 (xx) | 1972-08-04 |
| NO136671C (no) | 1977-10-19 |
| DE2063406B2 (de) | 1977-08-25 |
| IL38430A0 (en) | 1972-02-29 |
| DK129654C (xx) | 1975-04-01 |
| IE36110L (en) | 1972-06-23 |
| CH593302A5 (xx) | 1977-11-30 |
| FI50248C (fi) | 1976-01-12 |
| DE2063406C3 (de) | 1978-05-03 |
| GB1374079A (en) | 1974-11-13 |
| NL7117645A (xx) | 1972-06-27 |
| JPS5741480B1 (xx) | 1982-09-03 |
| NO136671B (xx) | 1977-07-11 |
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