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US4774236A
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17α-(substituted-methyl)-17β-hydroxy/esterified hydroxy steroids and pharmaceutical compositions containing them
Assignee: RTI International
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Filing: 1986-09-17
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Granted: 1988-09-27
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Expires: 2006-09-17
Abstract
Abstract Steroids of the formula: <IMAGE> <IMAGE> +TR <IMAGE> which are characterized by a 17 alpha -cyanomethyl, azidomethyl, methoxymethyl, phenylmethyl, or ethynylmethyl substituent and a 17 beta -hydroxy/esterified hydroxy substituent. The steroids of this invention have glucocorticoid, anti-glucocorticoid, progestational, or anti-progestational activity, depending on the particular structure.
Inventors
- 👤 C. Edgar Cook
- 👤 C. Ray Tallent
- 👤 Jerry R. Reel
- 👤 Mansukh C. Wani
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 13:59
CPC Classifications
C; C07; C07J; C07J41/00; C07J41/0005; C07J41/0016; C07J41/0033; C07J41/0077; C07J41/0083; C07J51/00
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
85 words
A steroid having binding affinity for the glucocorticoid receptor and possessing glucocorticoid activity, selected from the group represented by partial formula (II), wherein Z is selected from partial structures (III) or (IV), ##STR23## wherein: X is selected from the group consisting of --C.tbd.CH, CN, N 3 , SCN, OMe, and Ph; R is acetyl, propionyl or butyryl; R 1 is methyl; R 2 is α-H, β-OH or ═O, with the proviso that when X is CN, R 2 is ═O; and R 3 is H.
Claim 2
Dependent Claim
85 words
A steroid having binding affinity for the glucocorticoid receptor and possessing glucocorticoid activity, selected from the group represented by partial formula (II), wherein Z is selected from partial structures (III) or (IV), ##STR23## wherein: X is selected from the group consisting of --C.tbd.CH, CN, N 3 , SCN, OMe, and Ph; R is acetyl, propionyl or butyryl; R 1 is methyl; R 2 is α-H, β-OH or ═O, with the proviso that when X is CN, R 2 is ═O; and R 3 is H.
Claim 3
Dependent Claim
14 words
A steroid according to claim 1, wherein X is CN, N 3 or OMe.
Claim 4
Dependent Claim
28 words
A method of inducing a glucocorticoid hormonal response, which comprises administering an effective amount of a steroid according to claim 1, to a warm-blooded mammal in need thereof.
Claim 5
Dependent Claim
17 words
The method of claim 3, wherein said warm-blooded mammal is a primate, domestic pet or farm animal.
Claim 6
Dependent Claim
19 words
The method of claim 3, wherein the unit dose of the steroid lies between 0.0001 grams and 1.0 gram.
Claim 7
Dependent Claim
182 words
A steroid having binding affinity for the glucocorticoid receptor and possessing antiglucocorticoid activity, selected from the group represented by partial formula II, wherein Z has partial structure III, ##STR24## wherein: X is selected from the group consisting of N 3 , SCN, and Ph; R is H or C 1 -C 5 acyl; R 1 is methyl or ethyl; R 2 is α-H and an 11β-substituent selected from the group consisting of: (A) --(CH 2 ) n R 5 wherein n≦4 and R 5 =pyridyl, thiazolyl, --NMe 2 , --NEt 2 , ##STR25## OMe; (B) --C 6 H 4 .R 4 wherein R 4 is selected from among the substituents in R 5 or wherein R 4 =--H, --OCH 2 CH 2 NMe 2 , --OCH 2 CH 2 NEt 2 , or --O--(C 1 -C 3 ) alkyl; (C) -halogen, --S--(C 1 -C 3 ) alkyl, --S(O)--(C 1 -C 3 ) alkyl; (D) -S-phenyl, or --S(O)-phenyl; or R 2 is α-H, β-CF 3 ; α-H, β-CHF 2 ; ═CHF; or --CF 2 and R 3 is H or CH 3 .
Claim 8
Dependent Claim
182 words
A steroid having binding affinity for the glucocorticoid receptor and possessing antiglucocorticoid activity, selected from the group represented by partial formula II, wherein Z has partial structure III, ##STR24## wherein: X is selected from the group consisting of N 3 , SCN, and Ph; R is H or C 1 -C 5 acyl; R 1 is methyl or ethyl; R 2 is α-H and an 11β-substituent selected from the group consisting of: (A) --(CH 2 ) n R 5 wherein n≦4 and R 5 =pyridyl, thiazolyl, --NMe 2 , --NEt 2 , ##STR25## OMe; (B) --C 6 H 4 .R 4 wherein R 4 is selected from among the substituents in R 5 or wherein R 4 =--H, --OCH 2 CH 2 NMe 2 , --OCH 2 CH 2 NEt 2 , or --O--(C 1 -C 3 ) alkyl; (C) -halogen, --S--(C 1 -C 3 ) alkyl, --S(O)--(C 1 -C 3 ) alkyl; (D) -S-phenyl, or --S(O)-phenyl; or R 2 is α-H, β-CF 3 ; α-H, β-CHF 2 ; ═CHF; or --CF 2 and R 3 is H or CH 3 .
Claim 9
Dependent Claim
21 words
A steroid according to claim 6, wherein R 2 is α-H and an 11β-substituent selected from the group consisting of: ##STR26##
Claim 10
Dependent Claim
13 words
A steroid according to claim 6, wherein R is acetyl, propionyl or butyryl.
Claim 11
Dependent Claim
27 words
A method of inducing an anti-glucocorticoid antihormonal response, which comprises administering an effective amount of a steroid of claim 6, to a warm-blooded mammal in need thereof.
Claim 12
Dependent Claim
17 words
The method of claim 9, wherein said warm-blooded mammal is a primate, domestic pet or farm animal.
Claim 13
Dependent Claim
19 words
The method of claim 9 wherein the unit dose of the steroid lies between 0.0001 grams and 1.0 gram.
Claim 14
Dependent Claim
175 words
A steroid having binding affinity for the progesterone receptor and possessing antiprogestational activity, selected from the group represented by partial formula II, wherein Z has partial structure III, ##STR27## wherein: X is selected from the group consisting of N 3 ; SCN; and Ph; R is H or lower acyl; R 1 is methyl or ethyl; R 2 is α-H and an 11β-substituent selected from the group consisting of: (A) --(CH 2 ) n R 5 wherein n≦4 and R 5 =pyridyl, thiazolyl, --NMe 2 , --NEt 2 , ##STR28## --OMe; (B) --C 6 H 4 .R 4 wherein R 4 is selected from among the substituents in R 5 or wherein R 4 =--H, --OCH 2 CH 2 NMe 2 , --OCH 2 CH 2 NEt 2 , or --O--(C 1 -C 3 ) alkyl; (C) -halogen, --S--(C 1 -C 3 ) alkyl, --S(O)--(C 1 -C 3 ) alkyl; (D) -S-phenyl, or --S(O)-phenyl; or R 2 is α-H, β-CHF 2 ; ═CHF or ═CF 2 and R 3 is H or CH 3 .
Claim 15
Dependent Claim
175 words
A steroid having binding affinity for the progesterone receptor and possessing antiprogestational activity, selected from the group represented by partial formula II, wherein Z has partial structure III, ##STR27## wherein: X is selected from the group consisting of N 3 ; SCN; and Ph; R is H or lower acyl; R 1 is methyl or ethyl; R 2 is α-H and an 11β-substituent selected from the group consisting of: (A) --(CH 2 ) n R 5 wherein n≦4 and R 5 =pyridyl, thiazolyl, --NMe 2 , --NEt 2 , ##STR28## --OMe; (B) --C 6 H 4 .R 4 wherein R 4 is selected from among the substituents in R 5 or wherein R 4 =--H, --OCH 2 CH 2 NMe 2 , --OCH 2 CH 2 NEt 2 , or --O--(C 1 -C 3 ) alkyl; (C) -halogen, --S--(C 1 -C 3 ) alkyl, --S(O)--(C 1 -C 3 ) alkyl; (D) -S-phenyl, or --S(O)-phenyl; or R 2 is α-H, β-CHF 2 ; ═CHF or ═CF 2 and R 3 is H or CH 3 .
Claim 16
Dependent Claim
21 words
A steroid according to claim 12, wherein R 2 is α-H and an 11β-substituent selected from the group consisting of: ##STR29##
Claim 17
Dependent Claim
13 words
A steroid according to claim 12, wherein R is acetyl, propionyl, or butyryl.
Claim 18
Dependent Claim
27 words
A method of inducing an anti-progestational anti-hormonal response, which comprises administering an effective amount of a steroid of claim 12 to a warm-blooded mammal in need thereof.
Claim 19
Dependent Claim
17 words
The method of claim 15, wherein said warm-blooded mammal is a primate, domestic pet or farm animal.
Claim 20
Dependent Claim
19 words
The method of claim 15, wherein the unit dose of the steroid lies between 0.0001 grams and 1.0 gram.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-09-27 | 1992-03-28 | 1992-09-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-09-27 | 1996-03-28 | 1996-09-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-09-27 | 2000-03-28 | 2000-09-27 | $7700.00 | Window Closed / Lapsed |