GB1055353A - Process for the preparation of 3-hydroxy-and 3-alkoxy-estratrienes and intermediates therefor - Google Patents
Process for the preparation of 3-hydroxy-and 3-alkoxy-estratrienes and intermediates thereforInfo
- Publication number
- GB1055353A GB1055353A GB50273/63A GB5027363A GB1055353A GB 1055353 A GB1055353 A GB 1055353A GB 50273/63 A GB50273/63 A GB 50273/63A GB 5027363 A GB5027363 A GB 5027363A GB 1055353 A GB1055353 A GB 1055353A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyano
- androstene
- give
- formula
- dione
- 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
- 239000000543 intermediate Substances 0.000 title 1
- 239000005977 Ethylene Substances 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 2
- 229960001566 methyltestosterone Drugs 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- JWMFYGXQPXQEEM-GCOKGBOCSA-N 5α-pregnane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](CC)[C@@]2(C)CC1 JWMFYGXQPXQEEM-GCOKGBOCSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- LADUGMKTIJWWMV-YLXRRXKZSA-N N-[[(5R,8S,9S,10R,13S,14S)-13-methyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-10-yl]methylidene]hydroxylamine Chemical compound N(O)=C[C@]12CCCC[C@@H]1CC[C@H]1[C@@H]3CCC[C@@]3(C)CC[C@H]21 LADUGMKTIJWWMV-YLXRRXKZSA-N 0.000 abstract 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 abstract 1
- 239000004157 Nitrosyl chloride Substances 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 230000000397 acetylating effect Effects 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 abstract 1
- 238000006735 epoxidation reaction Methods 0.000 abstract 1
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 abstract 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 230000001678 irradiating effect Effects 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 abstract 1
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 abstract 1
- 235000019392 nitrosyl chloride Nutrition 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 150000004965 peroxy acids Chemical class 0.000 abstract 1
- 230000005855 radiation Effects 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
- 239000012279 sodium borohydride Substances 0.000 abstract 1
- 150000003431 steroids Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2485662 | 1962-12-19 | ||
| IT1999363A IT1051710B (it) | 1963-09-30 | 1963-09-30 | Procedimento per la preparazione di 3 ossi e 3 alcossi estratrieni |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1055353A true GB1055353A (en) | 1967-01-18 |
Family
ID=26327365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB50273/63A Expired GB1055353A (en) | 1962-12-19 | 1963-12-19 | Process for the preparation of 3-hydroxy-and 3-alkoxy-estratrienes and intermediates therefor |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3231567A (enrdf_load_stackoverflow) |
| BE (1) | BE641351A (enrdf_load_stackoverflow) |
| CH (1) | CH441304A (enrdf_load_stackoverflow) |
| DE (1) | DE1223379B (enrdf_load_stackoverflow) |
| DK (1) | DK104301C (enrdf_load_stackoverflow) |
| GB (1) | GB1055353A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3689512A (en) * | 1970-10-06 | 1972-09-05 | American Home Prod | Novel 3-etherified-1,3,5(10)-triene-steroids and process thereof |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3381003A (en) * | 1965-06-01 | 1968-04-30 | Merck & Co Inc | 3-keto-13beta-alkyl-17beta-acetyl-gona-4-ene-17alpha-ol compounds and processes of preparing them |
| US3487155A (en) * | 1968-02-19 | 1969-12-30 | Sandoz Ag | Substituted estradiol alkyl ethers |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2378918A (en) * | 1941-08-19 | 1945-06-26 | Squibb & Sons Inc | Cyclic ketals of keto-cyclopentanoperhydrophenanthrenes and methods of preparing them |
| US2729654A (en) * | 1954-05-19 | 1956-01-03 | Searle & Co | 10-hydroxy-3-ketosteroids |
-
0
- BE BE641351D patent/BE641351A/xx unknown
-
1963
- 1963-12-16 US US330584A patent/US3231567A/en not_active Expired - Lifetime
- 1963-12-17 CH CH1544763A patent/CH441304A/de unknown
- 1963-12-17 DK DK586663AA patent/DK104301C/da active
- 1963-12-17 DE DEV25048A patent/DE1223379B/de active Pending
- 1963-12-19 GB GB50273/63A patent/GB1055353A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3689512A (en) * | 1970-10-06 | 1972-09-05 | American Home Prod | Novel 3-etherified-1,3,5(10)-triene-steroids and process thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| US3231567A (en) | 1966-01-25 |
| DK104301C (da) | 1966-05-02 |
| CH441304A (de) | 1967-08-15 |
| DE1223379B (de) | 1966-08-25 |
| BE641351A (enrdf_load_stackoverflow) |
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