ES369990A1 - Procedure to produce a composite of prostaglandinas. (Machine-translation by Google Translate, not legally binding) - Google Patents
Procedure to produce a composite of prostaglandinas. (Machine-translation by Google Translate, not legally binding)Info
- Publication number
- ES369990A1 ES369990A1 ES369990A ES369990A ES369990A1 ES 369990 A1 ES369990 A1 ES 369990A1 ES 369990 A ES369990 A ES 369990A ES 369990 A ES369990 A ES 369990A ES 369990 A1 ES369990 A1 ES 369990A1
- Authority
- ES
- Spain
- Prior art keywords
- ethyl acetate
- formula
- translation
- procedure
- google translate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title abstract 3
- 239000002131 composite material Substances 0.000 title 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 4
- -1 prostaglandin compound Chemical class 0.000 abstract 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 239000011780 sodium chloride Substances 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000002024 ethyl acetate extract Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000000741 silica gel Substances 0.000 abstract 1
- 229910002027 silica gel Inorganic materials 0.000 abstract 1
- 229910052938 sodium sulfate Inorganic materials 0.000 abstract 1
- 235000011152 sodium sulphate Nutrition 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P31/00—Preparation of compounds containing a five-membered ring having two side-chains in ortho position to each other, and having at least one oxygen atom directly bound to the ring in ortho position to one of the side-chains, one side-chain containing, not directly bound to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having at least one oxygen atom bound in gamma-position to the ring, e.g. prostaglandins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Procedure for producing a prostaglandin compound of the formula: **(See formula)** where n is 1 to 8 and a is zero to 4; wherein R16 is hydrogen alkyl of 1 to 4 carbon atoms inclusive; where Y is isobutyl, tert-butyl, 3,3-difluoro-butyl, 4,4-difluorobutyl, or 4,4,4-trifluorobutyl and where it indicates binding of the group to the ring in alpha or beta configuration, characterized in that consists of dehydrating with acid a compound of the formula: **(See formula)** where R16, n, a, Y, and are defined as above, carrying out the operative process in successive phases as follows: a 200 mg solution of 19-methylprostaglandin E1 methyl ester, in a 2 ml mixture, of tetrahydrofuran and 2 ml, of 0.5N hydrochloric acid, stir in nitrogen, at 25ºC, for five days; the reaction mixture is then diluted with saturated aqueous sodium chloride solution and extracted with ethyl acetate; the ethyl acetate extract is washed with saturated aqueous sodium chloride solution; it is dried over sodium sulfate and evaporated to give 159 mg, of an oil; This is chromatographed on 25 g of silica gel and eluted with 350 ml of 20%, 400 ml of 30%, 500 ml of 40%, 1,000 ml of 50% and 500 ml of 60% acetate. of ethyl in Skellysolve B, and then with 500 ml of ethyl acetate, collecting 25 ml fractions; and eluate fractions 17-22 are concentrated and mixed to give 45 mg of 17-methyl-prostaglandin A1 methyl ester. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74815868A | 1968-07-29 | 1968-07-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES369990A1 true ES369990A1 (en) | 1971-12-16 |
Family
ID=25008268
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES369990A Expired ES369990A1 (en) | 1968-07-29 | 1969-07-29 | Procedure to produce a composite of prostaglandinas. (Machine-translation by Google Translate, not legally binding) |
| ES394672A Expired ES394672A1 (en) | 1968-07-29 | 1971-08-31 | Procedure to produce a composite of prostaglandinas. (Machine-translation by Google Translate, not legally binding) |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES394672A Expired ES394672A1 (en) | 1968-07-29 | 1971-08-31 | Procedure to produce a composite of prostaglandinas. (Machine-translation by Google Translate, not legally binding) |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE736726A (en) |
| CH (1) | CH532009A (en) |
| DE (1) | DE1937908A1 (en) |
| ES (2) | ES369990A1 (en) |
| FR (1) | FR2013927A1 (en) |
| IL (1) | IL32552A (en) |
| NL (1) | NL6911476A (en) |
| PL (1) | PL84082B1 (en) |
| SU (1) | SU385430A3 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1396206A (en) * | 1972-04-27 | 1975-06-04 | Upjohn Co | Prostaglandins and the preparation thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1198071A (en) * | 1966-08-09 | 1970-07-08 | George Erich Just | Improvements in or relating to Prostaglandin Analogues and the Manufacture thereof |
-
1969
- 1969-07-04 IL IL32552A patent/IL32552A/en unknown
- 1969-07-25 DE DE19691937908 patent/DE1937908A1/en active Pending
- 1969-07-25 NL NL6911476A patent/NL6911476A/xx unknown
- 1969-07-28 PL PL1969135099A patent/PL84082B1/en unknown
- 1969-07-28 CH CH1149769A patent/CH532009A/en not_active IP Right Cessation
- 1969-07-28 FR FR6925804A patent/FR2013927A1/en active Granted
- 1969-07-29 ES ES369990A patent/ES369990A1/en not_active Expired
- 1969-07-29 BE BE736726A patent/BE736726A/en unknown
- 1969-07-29 SU SU1353823A patent/SU385430A3/ru active
-
1971
- 1971-08-31 ES ES394672A patent/ES394672A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH532009A (en) | 1972-12-31 |
| NL6911476A (en) | 1970-02-02 |
| PL84082B1 (en) | 1976-02-28 |
| DE1937908A1 (en) | 1970-07-02 |
| FR2013927B1 (en) | 1973-01-12 |
| IL32552A (en) | 1975-07-28 |
| BE736726A (en) | 1970-01-29 |
| FR2013927A1 (en) | 1970-04-10 |
| ES394672A1 (en) | 1974-02-16 |
| IL32552A0 (en) | 1969-09-25 |
| SU385430A3 (en) | 1973-05-29 |
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