SE303486B - - Google Patents
Info
- Publication number
- SE303486B SE303486B SE728861A SE728861A SE303486B SE 303486 B SE303486 B SE 303486B SE 728861 A SE728861 A SE 728861A SE 728861 A SE728861 A SE 728861A SE 303486 B SE303486 B SE 303486B
- Authority
- SE
- Sweden
- Prior art keywords
- hydroxy
- steroids
- steroid
- oxo
- groups
- Prior art date
Links
- 239000002253 acid Substances 0.000 abstract 6
- 150000003431 steroids Chemical class 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 239000003638 chemical reducing agent Substances 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 125000000369 oxido group Chemical group [*]=O 0.000 abstract 2
- 125000004043 oxo group Chemical group O=* 0.000 abstract 2
- XIIAYQZJNBULGD-UHFFFAOYSA-N (5alpha)-cholestane Natural products C1CC2CCCCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 XIIAYQZJNBULGD-UHFFFAOYSA-N 0.000 abstract 1
- GKBHKNPLNHLYHT-UHFFFAOYSA-N 5beta-Stigmastan Natural products C1CC2CCCCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 GKBHKNPLNHLYHT-UHFFFAOYSA-N 0.000 abstract 1
- 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 1
- QSHQKIURKJITMZ-OBUPQJQESA-N 5β-cholane Chemical compound C([C@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCC)[C@@]2(C)CC1 QSHQKIURKJITMZ-OBUPQJQESA-N 0.000 abstract 1
- 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 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- LPEHPFZVJKRNRS-FWFZCRFUSA-N [(3s,5r,6r,8s,9s,10r,13s,14s)-5-chloro-6-hydroxy-10,13-dimethyl-17-oxo-2,3,4,6,7,8,9,11,12,14,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC[C@H]3[C@@H]1C[C@@H](O)[C@]1(Cl)[C@]2(C)CC[C@H](OC(=O)C)C1 LPEHPFZVJKRNRS-FWFZCRFUSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000005042 acyloxymethyl group Chemical group 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001737 cardanolides Chemical class 0.000 abstract 1
- XIIAYQZJNBULGD-LDHZKLTISA-N cholestane Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 XIIAYQZJNBULGD-LDHZKLTISA-N 0.000 abstract 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 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
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- INLFWQCRAJUDCR-LYLBMTSKSA-N spirostane Chemical class O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CCCCC4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 INLFWQCRAJUDCR-LYLBMTSKSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- GKBHKNPLNHLYHT-LWQAOISPSA-N stigmastane Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 GKBHKNPLNHLYHT-LWQAOISPSA-N 0.000 abstract 1
- LAGFCVRVICMFFF-UHFFFAOYSA-N stigmastane Natural products CCC(CCC(C)C1CCC2C3CCC4CC(=O)CC(C)C4C3CCC12C)C(C)C LAGFCVRVICMFFF-UHFFFAOYSA-N 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- 239000011701 zinc Substances 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
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 5-3-hydroxy- or -acyloxy-steroids of the androstane, pregnane or spirostane series containing in the 10-position a hydroxymethyl, acyloxymethyl, formyl, carboxy or carbalkoxy group; and a process for the preparation of any steroid containing a D 5-double bond and the aforementioned 3- and 10-substituents wherein a 5a -halogeno-6b , 19-steroid, a 19,6b -lactone of a 5a - halogeno - 6b - hydroxy - steroid 19 - acid or a 19,6b -cyclohemiacetal of a 10-formyl-5a -halogeno - 6b - hydroxy - steroid is treated with a reducing agent and, if desired, any hydroxy or 10-carboxy compound obtained is esterified or any hydroxy or 10-formyl compound obtained is oxidized and/or any ester obtained is hydrolysed. The starting material may belong to any of the steroid series mentioned above or to the cholane, cholestane, stigmastane or cardanolide series, and may contain free, ketalized or enolized oxo groups, esterified or etherified hydroxyl groups, alkyl groups of at most 7 carbon atoms or halogen atoms in one or more positions of the steroid nucleus or 17-side chain. They may also contain double bonds and oxido groups. When alkali or alkaline earth metals in liquid ammonia are used as reducing agents D 5-19-hydroxy-steroids are formed, and this may be accompanied by the reduction of other oxido groups or of oxo groups unless they have previously been protected. 19,6b -hemiacetals of 5a -halogeno-6b -hydroxy - 19 - oxo - steroids and 19,6b - lactones of the corresponding 19-acids can be reduced under mild conditions e.g. the use of zinc and an alcohol or an acid, to yield, respectively, D 5-19-oxo-steroids and D 5-steroid-19-acids. These may also be prepared by oxidation of the 19-hydroxy-steroids. The steroids of the invention may further be converted to 19-oxygenated D 4 - 3 - oxo - steroids and these may then be heated with an alkali metal hydroxide in an anhydrous or aqueous solution to give 19-nor - D 4 - 3 - oxo - steroids. Examples are given and an extensive list of esterifying acids is provided. The 19,6b - lactone of 3b - acetoxy - 5a -chloro - 6b - hydroxy - 17 - oxo - androstane - 19-acid is prepared by chromic acid oxidation of the corresponding 6b ,19 - oxido compound. Specifications 994,764, 994,748 and 994,750 are referred to.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH813360A CH412874A (en) | 1960-07-15 | 1960-07-15 | Process for the production of new 6B, 19-oxido-steroids |
| CH1210760A CH454840A (en) | 1960-10-28 | 1960-10-28 | Process for the production of steroid 19 acids |
| CH1439360A CH451925A (en) | 1960-12-23 | 1960-12-23 | Process for the preparation of 19-hydroxy steroids |
| CH399061 | 1961-04-05 | ||
| CH648161 | 1961-06-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SE303486B true SE303486B (en) | 1968-09-02 |
Family
ID=27509171
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE728861A SE303486B (en) | 1960-07-15 | 1961-07-13 |
Country Status (3)
| Country | Link |
|---|---|
| DK (1) | DK105586C (en) |
| GB (1) | GB994747A (en) |
| SE (1) | SE303486B (en) |
-
1961
- 1961-07-13 SE SE728861A patent/SE303486B/xx unknown
- 1961-07-14 DK DK291161A patent/DK105586C/en active
- 1961-07-17 GB GB2589561A patent/GB994747A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK105586C (en) | 1966-10-17 |
| GB994747A (en) | 1965-06-10 |
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