GB1082574A - Steroid esters - Google Patents
Steroid estersInfo
- Publication number
- GB1082574A GB1082574A GB1121067A GB1121067A GB1082574A GB 1082574 A GB1082574 A GB 1082574A GB 1121067 A GB1121067 A GB 1121067A GB 1121067 A GB1121067 A GB 1121067A GB 1082574 A GB1082574 A GB 1082574A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- methyl group
- nitrate
- group
- steroid esters
- 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
- -1 Steroid esters Chemical class 0.000 title 1
- 239000001257 hydrogen Substances 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 229910002651 NO3 Inorganic materials 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 229910052731 fluorine Chemical group 0.000 abstract 1
- 239000011737 fluorine Chemical group 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 abstract 1
- 238000006396 nitration reaction Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000011200 topical administration Methods 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
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
-
- 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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of formula <FORM:1082574/C2/1> wherein R is a C1- 6 alkyl group, R1 is hydrogen or a methyl group, R2 is hydrogen or a methyl group, R3 is chlorine or fluorine and R4 is hydrogen or a methyl group, provided that, at least one of R1 and R2 is hydrogen, which are prepared from the corresponding 11b ,17a -diols by nitration to form the 11-nitrate, acylation to form the 17-ester and removal of the nitrate group by a non-hydrolytic method, as claimed in Specification 1,082,573. The compounds of the invention have antiinflammatory activity and may be used in pharmaceutical compositions in combination with a carrier in forms suitable for topical administration.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB621565A GB1082573A (en) | 1965-02-12 | 1965-02-12 | Improvements in the preparation of steroid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1082574A true GB1082574A (en) | 1967-09-06 |
Family
ID=9810513
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1121067A Expired GB1082574A (en) | 1965-02-12 | 1965-02-12 | Steroid esters |
| GB621565A Expired GB1082573A (en) | 1965-02-12 | 1965-02-12 | Improvements in the preparation of steroid esters |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB621565A Expired GB1082573A (en) | 1965-02-12 | 1965-02-12 | Improvements in the preparation of steroid esters |
Country Status (7)
| Country | Link |
|---|---|
| CH (1) | CH452518A (en) |
| DE (1) | DE1568077A1 (en) |
| DK (1) | DK118557B (en) |
| FR (1) | FR5457M (en) |
| GB (2) | GB1082574A (en) |
| NO (1) | NO127190B (en) |
| SE (1) | SE326955B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997040836A1 (en) * | 1996-05-02 | 1997-11-06 | G.D. Searle & Co. | Novel pharmaceutical compositions having steroid nitrate ester derivatives useful as anti-inflammatory drugs |
| US5707984A (en) * | 1995-12-08 | 1998-01-13 | G. D. Searle & Co. | Steroid nitrite/nitrate ester derivatives useful as anti-inflammatory drugs |
| US5824669A (en) * | 1996-03-22 | 1998-10-20 | Nitromed, Inc. | Nitrosated and nitrosylated compounds and compositions and their use for treating respiratory disorders |
| US5837698A (en) * | 1996-05-02 | 1998-11-17 | G. D. Searle & Co. | Steroid nitrite and nitrate ester derivatives useful as anti-inflammatory drugs |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5792758A (en) * | 1995-12-08 | 1998-08-11 | G. D. Searle & Co. | Steroid nitrite ester derivatives useful as anti-inflammatory drugs |
-
1965
- 1965-02-12 GB GB1121067A patent/GB1082574A/en not_active Expired
- 1965-02-12 GB GB621565A patent/GB1082573A/en not_active Expired
-
1966
- 1966-02-02 NO NO16154566A patent/NO127190B/no unknown
- 1966-02-10 DK DK69066A patent/DK118557B/en unknown
- 1966-02-11 SE SE01806/66A patent/SE326955B/xx unknown
- 1966-02-11 DE DE19661568077 patent/DE1568077A1/en active Pending
- 1966-02-11 CH CH195666A patent/CH452518A/en unknown
- 1966-05-10 FR FR60887A patent/FR5457M/fr not_active Expired
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5707984A (en) * | 1995-12-08 | 1998-01-13 | G. D. Searle & Co. | Steroid nitrite/nitrate ester derivatives useful as anti-inflammatory drugs |
| US5824669A (en) * | 1996-03-22 | 1998-10-20 | Nitromed, Inc. | Nitrosated and nitrosylated compounds and compositions and their use for treating respiratory disorders |
| US6197762B1 (en) | 1996-03-22 | 2001-03-06 | Nitromed, Inc. | Nitrosated and nitrosylated steroids compositions, and methods for treating respiratory disorders |
| USRE37116E1 (en) * | 1996-03-22 | 2001-03-27 | Nitromed, Inc. | Nitrosated and nitrosylated compounds, and compositions and their use for treating respiratory disorders |
| US6579863B1 (en) | 1996-03-22 | 2003-06-17 | Nitromed, Inc. | Nitrosated and nitrosylated compounds and compositions and their use for treating respiratory disorders |
| US7160920B2 (en) | 1996-03-22 | 2007-01-09 | Nitromed, Inc. | Nitrosated and nitrosylated compounds and compositions and their use for treating respiratory disorders |
| US7345037B2 (en) | 1996-03-22 | 2008-03-18 | Nitromed, Inc. | Nitrosated and nitrosylated compounds and compositions and their use for treating respiratory disorders |
| WO1997040836A1 (en) * | 1996-05-02 | 1997-11-06 | G.D. Searle & Co. | Novel pharmaceutical compositions having steroid nitrate ester derivatives useful as anti-inflammatory drugs |
| US5837698A (en) * | 1996-05-02 | 1998-11-17 | G. D. Searle & Co. | Steroid nitrite and nitrate ester derivatives useful as anti-inflammatory drugs |
| US5985862A (en) * | 1996-05-02 | 1999-11-16 | G.D. Searle & Co. | Pharmaceutical compositions having steroid nitrate ester derivatives useful as anti-inflammatory drugs |
Also Published As
| Publication number | Publication date |
|---|---|
| CH452518A (en) | 1968-03-15 |
| NO127190B (en) | 1973-05-21 |
| FR5457M (en) | 1967-10-16 |
| DE1568077A1 (en) | 1970-03-12 |
| GB1082573A (en) | 1967-09-06 |
| SE326955B (en) | 1970-08-10 |
| DK118557B (en) | 1970-09-07 |
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