ES255441A1 - Procedure for the preparation of 16-methylene-steroids (Machine-translation by Google Translate, not legally binding) - Google Patents
Procedure for the preparation of 16-methylene-steroids (Machine-translation by Google Translate, not legally binding)Info
- Publication number
- ES255441A1 ES255441A1 ES0255441A ES255441A ES255441A1 ES 255441 A1 ES255441 A1 ES 255441A1 ES 0255441 A ES0255441 A ES 0255441A ES 255441 A ES255441 A ES 255441A ES 255441 A1 ES255441 A1 ES 255441A1
- Authority
- ES
- Spain
- Prior art keywords
- formula
- methylene
- steroids
- 17alpha
- formation
- 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 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 238000010561 standard procedure Methods 0.000 abstract 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 239000012670 alkaline solution Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 230000000640 hydroxylating effect Effects 0.000 abstract 1
- 238000011534 incubation Methods 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 230000002906 microbiologic effect Effects 0.000 abstract 1
- 244000005700 microbiome Species 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 150000003431 steroids Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Landscapes
- Steroid Compounds (AREA)
Abstract
Process for the preparation of 16-methylene steroids of the formula A ** (See formula) ** Z = H o well OR1 R1 = H or acyl X = H o well F and its 1-dehydro derivatives, characterized in that it is treated with an epoxidizing agent 16-methyl-5,16-pregnadien-3 beta-ol-20-one or its 3-acylate and in the 16alpha, 17alpha- oxide-steroid II thus prepared, in the order of succession that is desired, a) the 16beta-methyl-16alpha, 17alpha-oxide group is dissociated by treatment with acid, with formation of a 16-methylene group and a 17alpha-OH group, b) the 3beta-OR1-5-ene system is transformed by standard methods into the 3-keto-4-ene system, c) a hydroxyl group is introduced in position 11, by incubation with hydroxylating microorganisms, d) In order to prepare the corresponding steroids with an oxygen function in position 21, the substituent Z = H is replaced by consecutive treatment with elemental bromine or alkaline solution of iodine and alkaline acylate, by the radical Z = O-acyl, and e) In order to prepare the corresponding 1-dehydro-derivatives, the saturated 1,2-bond is transformed, by treatment with ordinary dehydration agents, chemical or microbiological, in a double bond 1,2 with formation of a compound of formula B ** (See formula) ** in which X and R1 have the meaning indicated above and another double bond may exist in position 1,2, and by the fact that, when a 16-methylene steroid of the formula A in which X = F is to be prepared, a fluorine atom in the 9alpha position is introduced into the compound B by standard methods, with formation of a compound of formula C ** (See formula) ** in which Z has the meaning indicated above and another double bond may exist in position 1,2. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE255441X | 1959-01-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES255441A1 true ES255441A1 (en) | 1960-04-16 |
Family
ID=38567653
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0255441A Expired ES255441A1 (en) | 1959-01-31 | 1960-01-30 | Procedure for the preparation of 16-methylene-steroids (Machine-translation by Google Translate, not legally binding) |
Country Status (1)
| Country | Link |
|---|---|
| ES (1) | ES255441A1 (en) |
-
1960
- 1960-01-30 ES ES0255441A patent/ES255441A1/en not_active Expired
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES255441A1 (en) | Procedure for the preparation of 16-methylene-steroids (Machine-translation by Google Translate, not legally binding) | |
| GB959869A (en) | Oxasteroids of the pregnane series | |
| ES280807A1 (en) | Procedure for preparing 6-alpha-methyl-16-methylene-steroids (Machine-translation by Google Translate, not legally binding) | |
| GB965929A (en) | Novel steroid compounds and their production | |
| ES261190A1 (en) | Procedure for the preparation of 16-methylene-steroids (Machine-translation by Google Translate, not legally binding) | |
| GB983125A (en) | Preparation of 9(11)-dehydro spirostanes and 3-esters thereof | |
| ES271609A1 (en) | Procedure for the preparation of 6-alpha-methyl-16-methyleneesteroids (Machine-translation by Google Translate, not legally binding) | |
| GB1015016A (en) | New steroid compounds and processes | |
| GB963287A (en) | New steroid compounds and processes for their preparation | |
| GB896818A (en) | Improvements in or relating to steroids and the manufacture thereof | |
| GB908770A (en) | A new steroid compound and its formation | |
| ES255518A1 (en) | Procedure for the preparation of steroids containing insufficient fluorine (Machine-translation by Google Translate, not legally binding) | |
| ES234326A1 (en) | Procedure for preparing steroids (Machine-translation by Google Translate, not legally binding) | |
| GB861799A (en) | Improvements in and relating to the manufacture of a steroid | |
| GB1045035A (en) | 1ª-methyl-í¸-5ª-androsten-17ª-ols and a process for their manufacture | |
| ES281479A1 (en) | PROCEDURE FOR OBTAINING STEROID COMPOUNDS | |
| GB1101791A (en) | New 1ª‡:7ª‡-dimethyl steroids and a process for their manufacture | |
| ES309455A1 (en) | Procedure for the preparation of 6-alpha-methyl-16-fluorometilen-steroides. (Machine-translation by Google Translate, not legally binding) | |
| ES312107A1 (en) | A procedure for the preparation of new compounds of steroid structure. (Machine-translation by Google Translate, not legally binding) | |
| ES254744A1 (en) | Procedure for the preparation of unsaturated 6-halogen-3-ceto-esteroides (Machine-translation by Google Translate, not legally binding) | |
| GB1117406A (en) | Process for dehydrohalogenating organic compounds | |
| GB973899A (en) | Novel steroid compounds and their preparation | |
| GB905526A (en) | Improvements in or relating to epoxysteroids | |
| GB934708A (en) | New steroid compounds and their production | |
| GB966102A (en) | Novel cyclopentanophenanthrene compounds and a process for the production thereof |