GB1214508A - 03-alkyl-11-oxygenated-18,19-dinorpregnenes - Google Patents
03-alkyl-11-oxygenated-18,19-dinorpregnenesInfo
- Publication number
- GB1214508A GB1214508A GB27161/70A GB2716170A GB1214508A GB 1214508 A GB1214508 A GB 1214508A GB 27161/70 A GB27161/70 A GB 27161/70A GB 2716170 A GB2716170 A GB 2716170A GB 1214508 A GB1214508 A GB 1214508A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- oxo
- protected
- group
- alkyl
- 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 8
- 125000004043 oxo group Chemical group O=* 0.000 abstract 8
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 150000003431 steroids Chemical class 0.000 abstract 2
- 230000000845 anti-microbial effect Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- 125000003700 epoxy group Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000003054 hormonal effect Effects 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 abstract 1
- 239000012285 osmium tetroxide Substances 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
-
- 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
-
- 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
- C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,214,508. 13 - Alkyl - 11 - oxygenated - -18,- 19-dinor-pregnenes. AMERICAN HOME PRODUCTS CORP. 19 Dec., 1967 [19 Dec., 1966 (2)], No. 27161/70. Divided out of 1,214,506. Heading C2U. Novel steroids of the formula where W is a hydroxy, oxo, protected hydroxy or protected oxo group; Y is a hydroxy or protected hydroxy group and ring A is aromatic or Y is etherified hydroxy and there is a 2,5(10)- diene system or Y is protected oxo and there is a 4-, 5(10)- or 5-double bond with or without a 2- or 3-double bond or Y is oxo and there is a 4- or 5(10)-double bond; R<SP>1</SP> is alkyl of at least 2 carbon atoms and R<SP>2</SP> is hydroxy or protected hydroxy and X is α- or #-hydroxy or protected hydroxy or oxo or protected oxo, or R<SP>1</SP> is alkyl and X and R<SP>2</SP> together form an epoxy group; and corresponding novel steroids of the above formula wherein R<SP>1</SP> is ethyl or n-propyl, the 17#-side chain is replaced by a vinyl group, R<SP>2</SP> is OH, W is protected OH and Y is oxo and there is a 4-double bond; are prepared, in the case of the first-mentioned group, by oxidation of 17- ethylidene steroids followed, where the groups R<SP>2</SP>, X, W and Y and the unsaturation are not the ones required, by one or more appropriate after-processes, and, in the case of the secondmentioned group, by elimination of p-toluenesulphonic acid from a corresponding 17-(1<SP>1</SP>- tosyloxyethyl) compound. Figs. 1 and 2 illustrate the invention in its preferred embodiments. The protecting groups are those known in the art which are readily convertible, e.g. by hydrolysis, to free hydroxy or oxo groups. The 13#- enantiomers may be in resolved or racemate form according as to whether the starting materials are resolved or racemic. dl - 11# - Acetoxy - 13# - ethyl - 3 - methoxygona- 1,3,5(10)-trien-17-one is a by-product in the oxidation of dl - 11# - acetoxy - 3 - methoxy- 13# - ethyl - 18,19 - dinorpregna - 1,3,5(10),17- (20)-tetraene with N-methylmorpholine oxidehydrogen peroxide in presence of osmium tetroxide. The novel 13#-alkyl-11-substituted-18,19-dinorpregnenes of Formula (II) above, which have corticoidal and/or other hormonal activities and some of which have antimicrobial activity may be made up into pharmaceutical compositions with suitable carriers.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60278566A | 1966-12-19 | 1966-12-19 | |
| US60276366A | 1966-12-19 | 1966-12-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1214508A true GB1214508A (en) | 1970-12-02 |
Family
ID=27084237
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27161/70A Expired GB1214508A (en) | 1966-12-19 | 1967-12-19 | 03-alkyl-11-oxygenated-18,19-dinorpregnenes |
| GB27160/70A Expired GB1214507A (en) | 1966-12-19 | 1967-12-19 | 03-alkyl-11-oxygenated-gonenes |
| GB57494/67A Expired GB1214506A (en) | 1966-12-19 | 1967-12-19 | 03-alkyl-3,11,17,20,21-pentaoxygenated-18,19-dinopregnenes and their derivatives |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27160/70A Expired GB1214507A (en) | 1966-12-19 | 1967-12-19 | 03-alkyl-11-oxygenated-gonenes |
| GB57494/67A Expired GB1214506A (en) | 1966-12-19 | 1967-12-19 | 03-alkyl-3,11,17,20,21-pentaoxygenated-18,19-dinopregnenes and their derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (3) | GB1214508A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5083517A (en) * | 1989-12-07 | 1992-01-28 | Stevens Joel H | Sod planting machine |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010522732A (en) * | 2007-03-29 | 2010-07-08 | ナームローゼ・フエンノートチヤツプ・オルガノン | Mineralocorticoid receptor antagonist |
-
1967
- 1967-12-19 GB GB27161/70A patent/GB1214508A/en not_active Expired
- 1967-12-19 GB GB27160/70A patent/GB1214507A/en not_active Expired
- 1967-12-19 GB GB57494/67A patent/GB1214506A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5083517A (en) * | 1989-12-07 | 1992-01-28 | Stevens Joel H | Sod planting machine |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1214506A (en) | 1970-12-02 |
| GB1214507A (en) | 1970-12-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |