US3989686A
Expired / Lapsed
US
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Anaesthetic steroids of the androstane series and process for preparing same
Assignee: Glaxo Laboratories Ltd
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Filing: 1974-09-13
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Granted: 1976-11-02
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Expires: 1994-09-13
Abstract
Abstract Anaesthetic steroids of the androstane and 19-norandrostane series are described, the steroids possessing a 3α-hydroxy group, a 17α-hydrogen atom and at the 17β-position a --COSH or esterified --COSH group.
Inventors
- 👤 Gordon Hanley Phillipps
- 👤 David Robert Marshall
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 19:01
CPC Classifications
C; C07; C07J; C07J31/00
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
149 words
A steriod of the formula: ##SPC1## where R 1 is hydrogen or methyl; R 2 is hydrogen or methyl; R 3 is hydrogen or when R 2 is hydrogen, C 1-6 alkoxy, C 1-5 alkyl, thiocyanato or halogen, R 4 is hydrogen or methyl; R 5 is C 1-6 alkyl or C 1-6 alkyl substituted by halogen or substituted by a group --NR 6 R 7 where R 6 and R 7 are the same or different C 1-6 alkyl groups or R 6 and R 7 taken together with the nitrogen atom to which they are attached form a group selected from the group consisting of morpholino, morpholino substituted with C 1-6 alkyl, and thiamorpholino and the dotted lines represent a double bond at either one of these positions, providing that R 2 and R 3 together represent hydrogen when there is a double bond at the 1,2-position.
Claim 2
Dependent Claim
149 words
A steriod of the formula: ##SPC1## where R 1 is hydrogen or methyl; R 2 is hydrogen or methyl; R 3 is hydrogen or when R 2 is hydrogen, C 1-6 alkoxy, C 1-5 alkyl, thiocyanato or halogen, R 4 is hydrogen or methyl; R 5 is C 1-6 alkyl or C 1-6 alkyl substituted by halogen or substituted by a group --NR 6 R 7 where R 6 and R 7 are the same or different C 1-6 alkyl groups or R 6 and R 7 taken together with the nitrogen atom to which they are attached form a group selected from the group consisting of morpholino, morpholino substituted with C 1-6 alkyl, and thiamorpholino and the dotted lines represent a double bond at either one of these positions, providing that R 2 and R 3 together represent hydrogen when there is a double bond at the 1,2-position.
Claim 3
Dependent Claim
17 words
A steriod according to claim 1, which is of the androstane series and contains a 5═-hydrogen atom.
Claim 4
Dependent Claim
34 words
A steroid according to claim 1 which contains a basic nitrogen atom, said steroid being in the form of its hydrochloride, hydrobromide, phosphate, sulphate, p-toluenesulphonate, methanesulphonate, citrate, tartrate, acetate, ascorbate, lactate, maleate or succinate.
Claim 5
Dependent Claim
10 words
A steroid according to claim 1 which is 3α-hydroxy-17β-methylthiocarbonly-5α-androstan-11-one; or
Claim 6
Dependent Claim
6 words
3α-hydroxy-17β-(2'morpholinoethyl-thiocarbonyl)-5αandrostan-11-one, and their physiologically acceptable salts.
Claim 7
Dependent Claim
6 words
3α-hydroxy-17β-(2'morpholinoethyl-thiocarbonyl)-5αandrostan-11-one, and their physiologically acceptable salts.
Claim 8
Dependent Claim
61 words
A process for the preparation of a compound as claimed in claim 1 which comprises: a. reacting a 17β-halocarbonyl androstane having a protected 3α-hydroxy group with a thiirane to form the corresponding 17β-(2'haloalkylthiocarbonyl) compound; b. reacting the (a) compound with ammonia, a primary or secondary amine to form a 17β-aminoalkythiocarbonyl compound; and c. regenerating the 3α-hydroxy group from its protected form.
Claim 9
Dependent Claim
15 words
A steroid according to claim 1 wherein R 3 is a C 1-6 alkoxy group.
Claim 10
Dependent Claim
23 words
A steroid according to claim 1 wherein R 5 is C 1-6 alkyl substituted by a morpholino group attached through the morpholino nitrogen.
References Cited (Backward Citations)
US3856828A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-11-02 | 1980-05-03 | 1980-11-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-11-02 | 1984-05-03 | 1984-11-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-11-02 | 1988-05-03 | 1988-11-02 | $7700.00 | Window Closed / Lapsed |