GB1193951A - 03-C2-4 Alkyl-Gonane Compounds - Google Patents
03-C2-4 Alkyl-Gonane CompoundsInfo
- Publication number
- GB1193951A GB1193951A GB2234366A GB2234366A GB1193951A GB 1193951 A GB1193951 A GB 1193951A GB 2234366 A GB2234366 A GB 2234366A GB 2234366 A GB2234366 A GB 2234366A GB 1193951 A GB1193951 A GB 1193951A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- reduction
- compounds
- ketal
- ester
- 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
- 230000009467 reduction Effects 0.000 abstract 4
- 238000006722 reduction reaction Methods 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- CNUGRHHHSQRLMF-JIUSCHCVSA-N 2-diazonio-1-[(8r,9s,10s,13s,14s,17s)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]ethenolate Chemical compound C1CCC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C([O-])=C[N+]#N)[C@@H]4[C@@H]3CCC21 CNUGRHHHSQRLMF-JIUSCHCVSA-N 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 239000003470 adrenal cortex hormone Substances 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 230000001195 anabolic effect Effects 0.000 abstract 1
- 230000003444 anaesthetic effect Effects 0.000 abstract 1
- 239000008280 blood Substances 0.000 abstract 1
- 210000004369 blood Anatomy 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- RKHQGWMMUURILY-UHRZLXHJSA-N cortivazol Chemical compound C([C@H]1[C@@H]2C[C@H]([C@]([C@@]2(C)C[C@H](O)[C@@H]1[C@@]1(C)C2)(O)C(=O)COC(C)=O)C)=C(C)C1=CC1=C2C=NN1C1=CC=CC=C1 RKHQGWMMUURILY-UHRZLXHJSA-N 0.000 abstract 1
- 238000006567 deketalization reaction Methods 0.000 abstract 1
- 230000000881 depressing effect Effects 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000000328 estrogen antagonist Substances 0.000 abstract 1
- 238000006266 etherification reaction Methods 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 238000005907 ketalization reaction Methods 0.000 abstract 1
- 150000002632 lipids Chemical class 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000000446 sulfanediyl group Chemical group *S* 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,193,951. 13-C 2-4 alkyl-gonane compounds. H. SMITH. 18 Aug., 1967 [19 May, 1966], No. 22343/66. Heading C2U. Novel steriods of the structure wherein R<SP>1</SP> is C 2-4 alkyl; Y is CH(OH) or an ester or ether thereof or a corresponding group with the 17-hydrogen atom replaced by a substituted or unsubstituted alkyl, alkenyl or alkynyl group, CO or a ketal thereof, CH(COCH 2 OH) or an ester thereof, CH(CH.OH.CH 2 - OH) or a mono- or di-ester thereof, or CH(CO 2 H) or a halide thereof; W is CH(OH) or CO or a ketal thereof; and ring A can optionally contain at least one halogen, alkyl or ethoxalyl substituent, are prepared by reduction of the corresponding #<SP>4</SP>-, #<SP>5</SP>- or #<SP>5(10)</SP>-gonenes. This reduction may be followed by one or more of the following processes: acylation, hydrolysis, oxidation and reduction in the 17-side chain, reduction of a 3-one to a 3-ol, ketalization of a 3-one, conversion of a 2-unsubstituted-3-one to a 2-alkyl-3-one, via for example, the 2-ethoxalyl compound if the 2-methyl compound is required, etherification of a 17-ol, conversion of a 17-one to a 17α-hydrocarbon-17#-ol, and deketalization of a 3-ketal. Also the 21-hydroxy- 20-ones and -ols and their acylates can be prepared from the 21-unsubstituted, 20-ones or the 17-halocarbonyl compounds by known methods e.g. conversion of a 17-halocarbonyl compound to a 21-diazopregnan-20-one and hydrolysis or acylolysis of thio. The steriods are of the dseries but may also be in admixture with those of the l-series, including racemic mixture. The 13-C 2-4 -alkylgonane compounds of the invention, which may variously have minerals corticoid, anaesthetic, anabolic, blood lipid depressing and estrogen antagonist activity, may be made up into pharmaceutical compositions with suitable carriers.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2234366A GB1193951A (en) | 1966-05-19 | 1966-05-19 | 03-C2-4 Alkyl-Gonane Compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2234366A GB1193951A (en) | 1966-05-19 | 1966-05-19 | 03-C2-4 Alkyl-Gonane Compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1193951A true GB1193951A (en) | 1970-06-03 |
Family
ID=10177866
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2234366A Expired GB1193951A (en) | 1966-05-19 | 1966-05-19 | 03-C2-4 Alkyl-Gonane Compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1193951A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102007063499A1 (en) | 2007-12-29 | 2009-07-02 | Bayer Schering Pharma Aktiengesellschaft | Steroid 17,17-lactol derivative, its use and the derivative containing drug |
-
1966
- 1966-05-19 GB GB2234366A patent/GB1193951A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102007063499A1 (en) | 2007-12-29 | 2009-07-02 | Bayer Schering Pharma Aktiengesellschaft | Steroid 17,17-lactol derivative, its use and the derivative containing drug |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PE20 | Patent expired after termination of 20 years |