Patent US4226862A successfully refreshed from Google Patents.
US4226862A
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Steroids and process for preparing the same
Assignee: Pierrel SpA
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Filing: 1975-02-26
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Granted: 1980-10-07
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Expires: 1995-02-26
Abstract
Abstract Novel steroids are described together with processes of making them and pharmaceutical compositions containing them. The steroids have pharmaceutical activity, especially anti-inflammatory activity. They are all 2-Bromo-6β-fluoro-pregna-1,4-diene-3,20-diones.
Inventors
- 👤 Mario Riva
- 👤 Gaetano Palladino
- 👤 Lucian Toscano
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 03:44
CPC Classifications
C; C07; C07J; C07J5/00; C07J5/0046; C07J5/0053; C07J5/0061; C07J5/0069; C07J5/0076; C07J5/0092; C07J71/00; C07J71/0005; C07J71/0026; C07J71/0031
Claims Analysis
Total Claims: 45
Claim 1
Independent Claim
103 words
Compounds having the formula: ##STR6## wherein X is Br, Cl or OQ; Y is Br, Cl, F or H; R 1 is OQ or an alkyl orthoester; R 2 is OQ; R 3 is H, αOQ, αCH 3 or βCH 3 ; and Q, which may be the same or different, is hydrogen or an acyl radical, or OQ in the 16, 17 or in the 17 and 21 positions may together form a cyclic ketal, cyclic acetal or cyclic alkyl orthoester; wherein at least one radical OQ is a carboxylic or an inorganic acid radical and pharmaceutically acceptable salts and esters thereof.
Claim 2
Dependent Claim
103 words
Compounds having the formula: ##STR6## wherein X is Br, Cl or OQ; Y is Br, Cl, F or H; R 1 is OQ or an alkyl orthoester; R 2 is OQ; R 3 is H, αOQ, αCH 3 or βCH 3 ; and Q, which may be the same or different, is hydrogen or an acyl radical, or OQ in the 16, 17 or in the 17 and 21 positions may together form a cyclic ketal, cyclic acetal or cyclic alkyl orthoester; wherein at least one radical OQ is a carboxylic or an inorganic acid radical and pharmaceutically acceptable salts and esters thereof.
Claim 3
Dependent Claim
9 words
Compounds according to claim 1 wherein X is OH.
Claim 4
Dependent Claim
9 words
Compounds according to claim 1 wherein Y is fluorine.
Claim 5
Dependent Claim
13 words
Compounds according to claim 1 wherein R 3 is α or β methyl.
Claim 6
Dependent Claim
22 words
Compounds according to claim 1 wherein Q in at least one of the 16, 17 or 21 positions is an acyl radical.
Claim 7
Dependent Claim
16 words
Compounds according to claim 1 wherein Q in the 16, 17 and 21 positions represents H.
Claim 8
Dependent Claim
15 words
Compounds according to claim 1 wherein OQ in the 21 position forms an alkyl orthoester.
Claim 9
Dependent Claim
18 words
Compounds according to claim 1 wherein OQ in the 21 position forms an inorganic ester with their salts.
Claim 10
Dependent Claim
17 words
A pharmaceutical composition comprising an active compound according to claim 1 together with a pharmaceutically acceptable carrier.
Claim 11
Dependent Claim
28 words
A method of combatting inflammation in a patient comprising applying a compound according to claim 1 to the patient topically or systemically in a non-toxic pharmaceutically effective amount.
Claim 12
Dependent Claim
97 words
Compounds having the formula: ##STR7## wherein X is Br, Cl or OQ; Y is Br, Cl, F or H; R 1 is OQ or an alkyl orthoester; R 2 is OQ; R 3 is H or αOQ; and Q which may be the same or different, is hydrogen or an acyl radical, or OQ in the 16, 17 or in the 17 and 21-positions may together form a cyclic ketal, cyclic acetal or cyclic alkyl orthoester; wherein at least one radical OQ is a carboxylic or an inorganic acid radical and pharmaceutically acceptable salts and esters thereof.
Claim 13
Dependent Claim
97 words
Compounds having the formula: ##STR7## wherein X is Br, Cl or OQ; Y is Br, Cl, F or H; R 1 is OQ or an alkyl orthoester; R 2 is OQ; R 3 is H or αOQ; and Q which may be the same or different, is hydrogen or an acyl radical, or OQ in the 16, 17 or in the 17 and 21-positions may together form a cyclic ketal, cyclic acetal or cyclic alkyl orthoester; wherein at least one radical OQ is a carboxylic or an inorganic acid radical and pharmaceutically acceptable salts and esters thereof.
Claim 14
Dependent Claim
127 words
A process of making a compound of the formula: ##STR8## wherein R 1 represents OQ or an orthoalkylester; R 2 represents OQ; R 3 represents H, αOQ, αCH 3 or αCH 3 ; and the radical Q, which may be the same or different, is H or acyl radicals, or the group OQ in the 16 and 17 positions or in the 17 and 21 positions may together form a cyclic ketal, cyclic acetal or cyclic alkyl orthoester, wherein at least one radical OQ is a carboxylic or an inorganic acid radical, which comprises reacting a compound of the formula: ##STR9## wherein R 1 and R 2 are as defined, and R 3 is hydrogen, methyl or αOH; with a brominating agent to yield the 2α-brominated product.
Claim 15
Dependent Claim
127 words
A process of making a compound of the formula: ##STR8## wherein R 1 represents OQ or an orthoalkylester; R 2 represents OQ; R 3 represents H, αOQ, αCH 3 or αCH 3 ; and the radical Q, which may be the same or different, is H or acyl radicals, or the group OQ in the 16 and 17 positions or in the 17 and 21 positions may together form a cyclic ketal, cyclic acetal or cyclic alkyl orthoester, wherein at least one radical OQ is a carboxylic or an inorganic acid radical, which comprises reacting a compound of the formula: ##STR9## wherein R 1 and R 2 are as defined, and R 3 is hydrogen, methyl or αOH; with a brominating agent to yield the 2α-brominated product.
Claim 16
Dependent Claim
69 words
A compound of the formula: ##STR10## wherein R 1 is OH or Oacyl; R 2 is OH, or Oacyl; R 3 is H, CH 3 , α OH or α Oacyl, or R 2 and R 3 together may represent the group ##STR11## X is F, Cl or Br and Y is Cl or OH; or X and Y form 9, 11 epoxy or a 9, 11 double bond.
Claim 17
Dependent Claim
69 words
A compound of the formula: ##STR10## wherein R 1 is OH or Oacyl; R 2 is OH, or Oacyl; R 3 is H, CH 3 , α OH or α Oacyl, or R 2 and R 3 together may represent the group ##STR11## X is F, Cl or Br and Y is Cl or OH; or X and Y form 9, 11 epoxy or a 9, 11 double bond.
Claim 18
Dependent Claim
8 words
The compound of claim 1 which is 2-bromo-6β,9α-difluoro-11β,17α,21-trihydroxy-pregna-1,4-diene-3,20-dione-17,21-diacetate.
Claim 19
Dependent Claim
15 words
A pharmaceutical composition comprising the compound of claim 14 together with a pharmaceutically acceptable carrier.
Claim 20
Dependent Claim
18 words
A method of combatting inflammation in a patient comprising applying the composition of claim 15 to the patient.
Claim 21
Dependent Claim
8 words
The compound of claim 13 which is 2-bromo-6β,9α-difluoro-11β,16α,17α,21-tetrahydroxy-pregna-1,4-diene-3,20-dione-21-acetate.
Claim 22
Dependent Claim
8 words
The compound of claim 13 which is 2-bromo-6β,9α-difluoro-11β,16α,17α,21-tetrahydroxy-pregna-1,4-diene-3,20-dione-21-acetate-16,17-acetonide.
Claim 23
Dependent Claim
8 words
The compound of claim 13, which is 2-bromo-6β-fluoro-9α,11β-dichloro-17α,21-dihydroxy-pregna-1,4-diene-17,21-diacetate.
Claim 24
Dependent Claim
8 words
The compound of claim 13 which is 16α-methyl-2-bromo-6β-fluoro-9α,11β-dichloro-17.alpha.,21-dihydroxy-pregna-1,4-diene-3,20-dione-17,21-diacetate.
Claim 25
Dependent Claim
8 words
The compound of claim 13 which is 16α-methyl-2-bromo-6β,9α-defluoro-11β,17α,21-trihydroxy-pregna-1,4-diene-3,20-dione-17,21-diacetate.
Claim 26
Dependent Claim
8 words
The compound of claim 13 which is 16β-methyl-2-bromo-6β-fluoro-9α,11β-dichloro-17.alpha.,21-dihydroxy-pregna-1,4-diene-3,20-dione-17,21-diacetate.
Claim 27
Dependent Claim
8 words
The compound of claim 13 which is 16β-methyl-2-bromo-6β,9α-difluoro-11β,17α,21-trihydroxy-pregna-1,4-diene-3,20-dione-17,21-diacetate.
Claim 28
Dependent Claim
9 words
The compound of claim 1 which is 2-bromo-6β,9α-difluoro-11β,16α,17α,21-tetrahydroxy-pregna-1,4-diene-3,20-dione, 16,21-diacetate.
Claim 29
Dependent Claim
30 words
The compound of claim 13 wherein X and Y form a 9,11 double bond, R 1 and R 2 are acetate, and R 3 is H, α or β methyl.
Claim 30
Dependent Claim
9 words
The compound of claim 25 which is 2-bromo-6β-fluoro-17α,-21-dihydroxy-pregna-1,4,9 (11)-triene-3,20-dione-17,21-diacetate.
Claim 31
Dependent Claim
8 words
The compound of claim 1 which is 2-bromo-6β,9α-difluoro-11β,17α,21-trihydroxy-pregna-1,4-diene-3,20-dione.
Claim 32
Dependent Claim
8 words
The compound of claim 1 which is 2-bromo-6β,9α-difluoro-11β,17α,21-trihydroxy-pregna-1,4-diene-3,20-dione-17,21-acetonide.
Claim 33
Dependent Claim
8 words
The compound of claim 1 which is 2-bromo-6β,9α-difluoro-11β,17α,21-trihydroxy-pregna-1,4-diene-3,20-dione-21-acetate.
Claim 34
Dependent Claim
8 words
The compound of claim 1 which is 2-bromo-6β,9α-difluoro-11β,17α,21-trihydroxy-pregna-1,4-diene-3,20-dione-21-propionate.
Claim 35
Dependent Claim
8 words
The compound of claim 1 which is 2-bromo-6β,9α-difluoro-11β,17α,21-trihydroxy-pregna-1,4-diene-3,20-dione-21-valerate.
Claim 36
Dependent Claim
8 words
The compound of claim 1 which is 2-bromo-6β,9α-difluoro-11β,17α,21-trihydroxy-pregna-1,4-diene-3,20-dione-21-pivalate.
Claim 37
Dependent Claim
9 words
The compound of claim 1 which is 2-bromo-6β,9α-difluoro-11β,17α,21-trihydroxy-pregna-1,4-diene-3,20-dione-21-terbutylacetate 6.
Claim 38
Dependent Claim
8 words
The compound of claim 1 which is 2-bromo-6β,9α-difluoro-11β,17α,21-trihydroxy-pregna-1,4-diene-3,20-dione-21-enantate.
Claim 39
Dependent Claim
8 words
The compound of claim 1 which is 2-bromo-6β,9α-difluoro-11β,17α,21-trihydroxy-pregna-1,4-diene-3,20-dione-21-benzoate.
Claim 40
Dependent Claim
8 words
The compound of claim 1 which is 2-bromo-6β,9α-difluoro-11β,17α,21-trihydroxy-pregna-1,4-diene-3,20-dione-17-valerate.
Claim 41
Dependent Claim
8 words
The compound of claim 1 which is 2-bromo-6β,9α-difluoro-11β,17α,21-trihydroxy-pregna-1,4-diene-3,20-dione-17-valerate-21-acetate.
Claim 42
Dependent Claim
8 words
The compound of claim 1 which is 2-bromo-6β,9α-difluoro-11β,17α,21-trihydroxy-pregna-1,4-diene-3,20-dione-17-acetate.
Claim 43
Dependent Claim
8 words
The compound of claim 1 which is 2-bromo-6β,9α-difluoro-11β,17α,21-trihydroxy-pregna-1,4-diene-3,20-dione-17-acetate-21-valerate.
Claim 44
Dependent Claim
8 words
The compound of claim 1 which is 2-bromo-6β,9α-difluoro-11β,17α,21-trihydroxy-pregna-1,4-diene-3,20-dione-17-propionate.
Claim 45
Dependent Claim
8 words
The compound of claim 1 which is 2-bromo-6β,9α-difluoro-11β,17α,21-trihydroxy-pregna-1,4-diene-3,20-dione-17-benzoate.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-10-07 | 1984-04-07 | 1984-10-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-10-07 | 1988-04-07 | 1988-10-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-10-07 | 1992-04-07 | 1992-10-07 | $7700.00 | Window Closed / Lapsed |