IL26917A - Process for the production of A6 - Fluoro - 16 - Methylene - A17 - Hydroxy - steroids from the Parganan series - Google Patents
Process for the production of A6 - Fluoro - 16 - Methylene - A17 - Hydroxy - steroids from the Parganan seriesInfo
- Publication number
- IL26917A IL26917A IL2691766A IL2691766A IL26917A IL 26917 A IL26917 A IL 26917A IL 2691766 A IL2691766 A IL 2691766A IL 2691766 A IL2691766 A IL 2691766A IL 26917 A IL26917 A IL 26917A
- Authority
- IL
- Israel
- Prior art keywords
- methylene
- steroids
- 6alpha
- 17alpha
- fluoro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 150000003128 pregnanes Chemical class 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000003431 steroids Chemical class 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- -1 methylene steroids Chemical class 0.000 claims 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- JWMFYGXQPXQEEM-NUNROCCHSA-N 5β-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-NUNROCCHSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- CPUKWYXYHPOQJH-RDQPJNLGSA-N (8r,9s,10s,13s,14s)-17-ethenyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1CCC[C@]2(C)[C@H]3CC[C@](C)(C(=CC4)C=C)[C@@H]4[C@@H]3CCC21 CPUKWYXYHPOQJH-RDQPJNLGSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- MOVRKLZUVNCBIP-RFZYENFJSA-N cortancyl Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)CC2=O MOVRKLZUVNCBIP-RFZYENFJSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229960003387 progesterone Drugs 0.000 description 1
- 239000000186 progesterone Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- 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
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM0067768 | 1965-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL26917A true IL26917A (en) | 1970-07-19 |
Family
ID=7312330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL2691766A IL26917A (en) | 1965-12-23 | 1966-11-23 | Process for the production of A6 - Fluoro - 16 - Methylene - A17 - Hydroxy - steroids from the Parganan series |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE691655A (enrdf_load_html_response) |
| CH (1) | CH476704A (enrdf_load_html_response) |
| DE (1) | DE1543256A1 (enrdf_load_html_response) |
| ES (1) | ES334816A1 (enrdf_load_html_response) |
| FR (1) | FR1505675A (enrdf_load_html_response) |
| GB (1) | GB1127167A (enrdf_load_html_response) |
| IL (1) | IL26917A (enrdf_load_html_response) |
| NL (1) | NL6615761A (enrdf_load_html_response) |
| SE (1) | SE304003B (enrdf_load_html_response) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4599463A (en) * | 1984-12-24 | 1986-07-08 | General Electric Company | Process for the preparation of bisphenols |
-
1965
- 1965-12-23 DE DE19651543256 patent/DE1543256A1/de active Pending
-
1966
- 1966-10-10 CH CH1458566A patent/CH476704A/de not_active IP Right Cessation
- 1966-11-08 NL NL6615761A patent/NL6615761A/xx unknown
- 1966-11-18 GB GB5173866A patent/GB1127167A/en not_active Expired
- 1966-11-23 IL IL2691766A patent/IL26917A/en unknown
- 1966-12-08 FR FR86634A patent/FR1505675A/fr not_active Expired
- 1966-12-21 SE SE1749866A patent/SE304003B/xx unknown
- 1966-12-22 ES ES334816A patent/ES334816A1/es not_active Expired
- 1966-12-22 BE BE691655D patent/BE691655A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE691655A (enrdf_load_html_response) | 1967-06-22 |
| ES334816A1 (es) | 1968-03-01 |
| CH476704A (de) | 1969-08-15 |
| NL6615761A (enrdf_load_html_response) | 1967-06-26 |
| DE1543256A1 (de) | 1969-09-11 |
| SE304003B (enrdf_load_html_response) | 1968-09-16 |
| FR1505675A (fr) | 1967-12-15 |
| GB1127167A (en) | 1968-09-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2777843A (en) | Preparation of 4-pregnen-17alpha-ol-3, 20-dione | |
| IL26917A (en) | Process for the production of A6 - Fluoro - 16 - Methylene - A17 - Hydroxy - steroids from the Parganan series | |
| US2779773A (en) | Steroid 3, 16alpha-diols and process | |
| US2341081A (en) | Compounds of the cyclopentanopolyhydrophenanthrene series and process for the manufacture thereof | |
| US2906758A (en) | 3-(hydroxyalkyl)-ethers of estradiol | |
| US2700666A (en) | Method of preparing cortisone derivatives | |
| US2751379A (en) | Preparation of steroidal 11alpha-hydroxy compounds | |
| US2990414A (en) | 17-undecenoate of estradiol | |
| DE2023122B2 (de) | Verfahren zur Herstellung von Pregnen-Derivaten | |
| US3062843A (en) | C-2-carboxylic acid and c-2-hydroxymethyl derivatives of the androstane series | |
| US3249628A (en) | Delta1, 3-androstadiene-3, 17beta-diol-3-benzyl ether and process for the productionthereof | |
| US3096350A (en) | 6, 16alpha-dimethyl-delta1, 4, 6-pregnatriene-17alpha-ol-3, 20-dione and esters thereof | |
| US3102897A (en) | 6-halo-19-nor-delta4,6-androstadien-17beta-ol-3-one derivatives | |
| US3741955A (en) | 3beta-hydroxy - 14,15beta-oxido - 14beta-bufa-4,20,22-trienalide-3beta-(alpha-l-rhamnopyranoside) | |
| US3062845A (en) | Process for the conversion of alpha-acetyl steroids to beta-acetyl steroids and intermediates therein | |
| US2713588A (en) | 3 beta, 11alpha-dihydroxyallopregnane-20-one and esters thereof | |
| US2167132A (en) | Process for the preparation of derivatives of estradiol | |
| AT271747B (de) | Verfahren zur Herstellung neuer 9β, 10α Steroide | |
| US3099656A (en) | delta3,5-pregnadiene derivatives | |
| US2964543A (en) | 3, 17-bisoxygenated androst-4-en-9alpha-ols | |
| US3004966A (en) | 6-methyl steroid compounds and method for preparing same | |
| US2615017A (en) | Steroid compounds | |
| US3082221A (en) | 4-chloro-6alpha-methyl derivatives of testosterone | |
| US2833790A (en) | 5-halo-17(20)-bisnorcholenal compounds and process for preparing same | |
| CH494213A (de) | Verfahren zur Herstellung von Gonadienonen |