GB898294A - Improvements in or relating to steroids and the manufacture thereof - Google Patents
Improvements in or relating to steroids and the manufacture thereofInfo
- Publication number
- GB898294A GB898294A GB20009/61A GB2000961A GB898294A GB 898294 A GB898294 A GB 898294A GB 20009/61 A GB20009/61 A GB 20009/61A GB 2000961 A GB2000961 A GB 2000961A GB 898294 A GB898294 A GB 898294A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- fluoro
- compound
- hydroxymethylene
- dione
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000003431 steroids Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 239000011737 fluorine Chemical group 0.000 abstract 2
- 239000001257 hydrogen Chemical group 0.000 abstract 2
- 229910052739 hydrogen Chemical group 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229930193140 Neomycin Natural products 0.000 abstract 1
- YJQPYGGHQPGBLI-UHFFFAOYSA-N Novobiocin Natural products O1C(C)(C)C(OC)C(OC(N)=O)C(O)C1OC1=CC=C(C(O)=C(NC(=O)C=2C=C(CC=C(C)C)C(O)=CC=2)C(=O)O2)C2=C1C YJQPYGGHQPGBLI-UHFFFAOYSA-N 0.000 abstract 1
- 229930182555 Penicillin Natural products 0.000 abstract 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 abstract 1
- 239000004133 Sodium thiosulphate Substances 0.000 abstract 1
- 239000004098 Tetracycline Substances 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229960005091 chloramphenicol Drugs 0.000 abstract 1
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229960004927 neomycin Drugs 0.000 abstract 1
- 229960002950 novobiocin Drugs 0.000 abstract 1
- YJQPYGGHQPGBLI-KGSXXDOSSA-N novobiocin Chemical compound O1C(C)(C)[C@H](OC)[C@@H](OC(N)=O)[C@@H](O)[C@@H]1OC1=CC=C(C(O)=C(NC(=O)C=2C=C(CC=C(C)C)C(O)=CC=2)C(=O)O2)C2=C1C YJQPYGGHQPGBLI-KGSXXDOSSA-N 0.000 abstract 1
- 239000002674 ointment Substances 0.000 abstract 1
- 239000003791 organic solvent mixture Substances 0.000 abstract 1
- 150000002960 penicillins Chemical class 0.000 abstract 1
- 239000008024 pharmaceutical diluent Substances 0.000 abstract 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 abstract 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 abstract 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 abstract 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 abstract 1
- 235000009518 sodium iodide Nutrition 0.000 abstract 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 abstract 1
- 235000019345 sodium thiosulphate Nutrition 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 229960002180 tetracycline Drugs 0.000 abstract 1
- 229930101283 tetracycline Natural products 0.000 abstract 1
- 235000019364 tetracycline Nutrition 0.000 abstract 1
- 150000003522 tetracyclines Chemical class 0.000 abstract 1
Classifications
-
- 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
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds having the formula <FORM:0898294/IV (b)/1> wherein X is chlorine, fluorine or hydrogen and Y is b -hydroxymethylene or carbonyl and processes for the preparation thereof by treating a compound having the formula <FORM:0898294/IV (b)/2> wherein the dotted line represents a single or double bond linkage and R is an aryl or alkyl sulphonyl radical, with sodium iodide in acetone solution and subjecting the 21-iodo compound so produced to reduction. The reduction may be effected with sodium thiosulphate, sodium bisulphite, or potassium bisulphite in an aqueous organic solvent mixture. Illustrative products of the invention are 6a -fluoro-11b ,17a -dihydroxy-16b - methyl - 1, 4 - pregnadiene - 3, 20 - dione, 6a - fluoro - 11b , 17a - dihydroxy - 16b - methyl - 4-pregnene-3,20-dione and the corresponding 9a -fluoro compounds.ALSO:Anti-inflammatory compositions comprise a compound having the formula <FORM:0898294/VI/1> wherein X is hydrogen, fluorine or chlorine, Y is b -hydroxymethylene or carbonyl and the dotted line represents a single or double bond linkage, and a pharmaceutical diluent. They are employed as ointments, tablets and suspensions, with or without coacting antibiotics e.g. penicillins, neomycin, tetracycline, chloramphenicol and novobiocin.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80009059A | 1959-03-18 | 1959-03-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB898294A true GB898294A (en) | 1962-06-06 |
Family
ID=25177458
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20009/61A Expired GB898294A (en) | 1959-03-18 | 1960-03-14 | Improvements in or relating to steroids and the manufacture thereof |
| GB8925/60A Expired GB898293A (en) | 1959-03-18 | 1960-03-14 | Improvements in or relating to steroids and the manufacture thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8925/60A Expired GB898293A (en) | 1959-03-18 | 1960-03-14 | Improvements in or relating to steroids and the manufacture thereof |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE588796A (en) |
| CH (2) | CH397670A (en) |
| DE (1) | DE1443176A1 (en) |
| DK (1) | DK108860C (en) |
| FR (2) | FR1467005A (en) |
| GB (2) | GB898294A (en) |
| SE (3) | SE307352B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2010458B2 (en) * | 1970-02-28 | 1979-04-26 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | New 21-Halogen Steroids |
-
1960
- 1960-02-18 DK DK33061AA patent/DK108860C/en active
- 1960-03-11 SE SE2497/60A patent/SE307352B/xx unknown
- 1960-03-14 GB GB20009/61A patent/GB898294A/en not_active Expired
- 1960-03-14 GB GB8925/60A patent/GB898293A/en not_active Expired
- 1960-03-15 CH CH216465A patent/CH397670A/en unknown
- 1960-03-15 CH CH291260A patent/CH397668A/en unknown
- 1960-03-17 FR FR821680A patent/FR1467005A/en not_active Expired
- 1960-03-17 DE DE19601443176 patent/DE1443176A1/en active Pending
- 1960-03-18 BE BE588796A patent/BE588796A/en unknown
- 1960-08-30 FR FR837260A patent/FR493M/fr active Active
-
1963
- 1963-10-04 SE SE10884/63A patent/SE312335B/xx unknown
- 1963-10-04 SE SE10885/63A patent/SE312555B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR1467005A (en) | 1967-01-27 |
| DE1443176A1 (en) | 1968-12-19 |
| SE307352B (en) | 1969-01-07 |
| SE312335B (en) | 1969-07-14 |
| CH397668A (en) | 1965-08-31 |
| DK108860C (en) | 1968-02-19 |
| FR493M (en) | 1961-05-08 |
| CH397670A (en) | 1965-08-31 |
| GB898293A (en) | 1962-06-06 |
| SE312555B (en) | 1969-07-21 |
| BE588796A (en) | 1960-09-19 |
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