GB909201A - New steroid products and process of preparing them - Google Patents
New steroid products and process of preparing themInfo
- Publication number
- GB909201A GB909201A GB13767/61A GB1376761A GB909201A GB 909201 A GB909201 A GB 909201A GB 13767/61 A GB13767/61 A GB 13767/61A GB 1376761 A GB1376761 A GB 1376761A GB 909201 A GB909201 A GB 909201A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- hydrogen
- acid
- androsten
- double bond
- 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
- 150000003431 steroids Chemical class 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 150000002596 lactones Chemical group 0.000 abstract 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 229930194542 Keto Natural products 0.000 abstract 2
- 125000000468 ketone group Chemical group 0.000 abstract 2
- 229910052763 palladium Inorganic materials 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- -1 steroid lactones Chemical class 0.000 abstract 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 2
- PHGUEOWJJYYXEP-VNCHUVBTSA-N 4-hydroxy-4-[(3S,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid Chemical compound OC(CCC(=O)O)(C)[C@@H]1[C@]2(C)[C@@H](CC1)[C@@H]1CC[C@H]3C[C@H](CC[C@]3(C)[C@H]1CC2)O PHGUEOWJJYYXEP-VNCHUVBTSA-N 0.000 abstract 1
- CPKPYGMPIQXHLR-MMRNZBBESA-N 4-hydroxy-4-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pent-2-enoic acid Chemical compound OC(C=CC(=O)O)(C)[C@@H]1[C@]2(C)[C@@H](CC1)[C@@H]1CC=C3C[C@H](CC[C@]3(C)[C@H]1CC2)O CPKPYGMPIQXHLR-MMRNZBBESA-N 0.000 abstract 1
- BTVSKHJYYXZPNX-MMRNZBBESA-N 4-hydroxy-4-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid Chemical compound OC(CCC(=O)O)(C)[C@@H]1[C@]2(C)[C@@H](CC1)[C@@H]1CC=C3C[C@H](CC[C@]3(C)[C@H]1CC2)O BTVSKHJYYXZPNX-MMRNZBBESA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000004652 butanoic acids Chemical class 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 150000001261 hydroxy acids Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- LROBJRRFCPYLIT-UHFFFAOYSA-M magnesium;ethyne;bromide Chemical compound [Mg+2].[Br-].[C-]#C LROBJRRFCPYLIT-UHFFFAOYSA-M 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- ORNBQBCIOKFOEO-QGVNFLHTSA-N pregnenolone Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 ORNBQBCIOKFOEO-QGVNFLHTSA-N 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical class CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J19/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 by a lactone ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
- A61K31/585—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin containing lactone rings, e.g. oxandrolone, bufalin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises steroid lactones of the general formula <FORM:0909201/IV (b)/1> wherein Y represents hydrogen or methyl (there either is or is not a 2:3 double bond in the lactone ring), X represents keto, b -hydroxy and a -hydrogen, or b -acyloxy and a -hydrogen where the acyl radical is derived from an aliphatic acid containing from 1 to 9 carbon atoms, and wherein when X represents keto there is either a 4:5 double bond or a 5a -hydrogen atom, and when X is b -hydroxy (or acyloxy) and a -hydrogen there is either a 5:6-double bond or a 5a -hydrogen atom but not 2:3-double bond in the lactone ring, the salts produced by treating the above lactones with alkali, and the corresponding hydroxy-acids derived from the salts; and processes for the preparation of (a) the lactone of 4-hydroxy4 - (3b -hydroxy-5-androsten-17b -yl)-2-pentenoic acid or the corresponding butenoic acid by hydrogenating the corresponding 2-pentinoic or butinoic acid with one mol of hydrogen in the presence of Lindlar palladium in tetrahydrofuran or alcohol solution, (b) the lactone of 4-hydroxy-4-(3b -hydroxy-5-androsten-17b -yl) pentanoic acid or of 4-hydroxy-4-(3b -hydroxy-5a -androstane-17b -yl) pentanoic acid or of either of the corresponding butanoic acids by hydrogenating 4-hydroxy-4-(3b -hydroxy-5-androsten-17b -yl) pentinoic acid or the corresponding butanoic acid in the presence of 10% palladium over carbon in tetrahydrofuran or alcohol solution until the requisite amount of hydrogen is absorbed, (c) the 3-acyloxy compounds defined by the general formula above by acylating the corresponding 3-hydroxy compounds, e.g. to form 3-acetates, propionates, valerates, b -phenylpropionates, b -cyclopentylpropionates and hemisuccinates and (d) the 3-keto compounds defined by the general formula above by oxidising the corresponding 3b -hydroxy compound having the double bond, if at all, in the 5:6 position. Therapeutic compositions useful as nutriuretics contain a steroid lactone of the above general formula and a solid and/or liquid pharmaceutically acceptable carrier. p 4-Hydroxy - 4 - (3b -hydroxy-5-androsten-17b -yl)-T-pentionic and -butinoic acids are prepared by reacting ethynyl magnesium bromide with pregn-5-en-3b -ol-20-one and 17b -formyl-5-androsten-3b -ol-3-acetate to form 20-ethynyl-21-nov-5-pregnene-3b ,20-diol respectively, and reacting the 20-ethynyl compounds with a Grignard reagent and then carboxylating with carbon dioxide.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT694760 | 1960-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB909201A true GB909201A (en) | 1962-10-31 |
Family
ID=11122612
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB13767/61A Expired GB909201A (en) | 1960-04-20 | 1961-04-17 | New steroid products and process of preparing them |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1078M (en) |
| GB (1) | GB909201A (en) |
-
1961
- 1961-04-17 GB GB13767/61A patent/GB909201A/en not_active Expired
- 1961-04-18 FR FR859056A patent/FR1078M/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1078M (en) | 1962-01-22 |
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