GB881501A - Substituted pregnenes - Google Patents
Substituted pregnenesInfo
- Publication number
- GB881501A GB881501A GB22566/59A GB2256659A GB881501A GB 881501 A GB881501 A GB 881501A GB 22566/59 A GB22566/59 A GB 22566/59A GB 2256659 A GB2256659 A GB 2256659A GB 881501 A GB881501 A GB 881501A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pregnene
- dione
- steroid
- group
- alkanoyl
- 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
- 150000003130 pregnenes Chemical class 0.000 title 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 2
- SUPOKHOQAKXOHJ-BYZMTCBYSA-N (8s,9s,10r,13r,14s,17s)-17-ethyl-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical class C1CC2=CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 SUPOKHOQAKXOHJ-BYZMTCBYSA-N 0.000 abstract 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 150000003431 steroids Chemical class 0.000 abstract 1
Classifications
-
- 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)
Abstract
The invention comprises D 4-pregnenes having the general formula <FORM:0881501/IV (b)/1> in which R is a hydrogen atom or a lower alkanoyl radical having 1-6 carbon atoms, X is a halogen atom and X1 is the divalent radical -CO- or -CHOH-, and a process for the preparation thereof which comprises (a) treating a D 4,9(11)-steroid of the general formula <FORM:0881501/IV (b)/2> in which R is a hydrogen atom or a lower alkanoyl alkanoyl group and R1 is hydrogen, or the 16 and 17 position is bonded together to form the 16a ,17a -methylenedioxy steroid, and -Y-Z-is the following <FORM:0881501/IV (b)/3> to form the 9a -halo-11b -hydroxy derivative, and then doing the following in any desired sequence (b) if desired, when R and R1 are bonded together to form the 16a ,17a -methylenedioxy or where R is a lower-alkanoyl group, oxidising to convert the 11b -hydroxy group to an 11-keto group (c) when the 16,17 positions form a <FORM:0881501/IV (b)/4> group, hydrolysing the product produced in step (a) or step (b) to convert to a product in which R and R1 form a hydrogen atom, (d) and further, if desired, when R is hydrogen, alkanoylating to form the 16a -lower-alkanoyl steroid of formula I. Conversion to the 9a -halo-11b -hydroxy steroid in step (a) may be effected with N-bromosuccinimide or 1,3-dichloro-5,5-dimethylhydantoin in the presence of a solvent and then with perchloric acid when -Y-Z- represents <FORM:0881501/IV (b)/5> or with hydrohalic acid when -Y-Z- is <FORM:0881501/IV (b)/6> Illustrative products of the invention are 16a -acetoxy - 9a - bromo - 11b ,17a - dihydroxy - 4 - pregnene - 3,20 - dione, 16a - acetoxy - 9a - chloro - 11b ,17a - dihydroxy - 4 - pregnene - 3,20 - dione, 9a - fluoro - 11b ,16a ,17a - trihydroxy - 4 - pregnene - 3,20 - dione, 16a - acetoxy - 9a - fluoro-11b ,17a - dihydroxy - 4 - pregnene - 3,20 - dione and 9a - bromo - 11b ,16a ,17a - trihydroxy - 4 - pregnene-3,20-dione.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US881501XA | 1958-07-09 | 1958-07-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB881501A true GB881501A (en) | 1961-11-01 |
Family
ID=22209643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB22566/59A Expired GB881501A (en) | 1958-07-09 | 1959-07-01 | Substituted pregnenes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB881501A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103588853A (en) * | 2013-11-28 | 2014-02-19 | 浙江省天台县奥锐特药业有限公司 | Method for preparing 9,11beta-epoxy steroid compound |
-
1959
- 1959-07-01 GB GB22566/59A patent/GB881501A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103588853A (en) * | 2013-11-28 | 2014-02-19 | 浙江省天台县奥锐特药业有限公司 | Method for preparing 9,11beta-epoxy steroid compound |
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