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US4181808A
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5-Keto prostaglandin Fα analogs
Assignee: Pharmacia and Upjohn Co
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Filing: 1978-08-11
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Granted: 1980-01-01
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Expires: 1998-08-11
Abstract
Abstract Prostaglandin (PG 1 derivatives having (1) a 5-keto feature, for example ##STR1## or (2) a 9-deoxy-5,9-epoxy feature together with a 4-halo or 5-hydroxy feature, for example ##STR2## or a 4,5-didehydro feature, for example in an enol ether of the formula ##STR3## said derivatives having pharmacological activity. Processes for preparing them and the appropriate intermediates are disclosed.
Inventors
- 👤 Roy A. Johnson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 04:06
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/77; C07D307/93; C07D307/935; C07C; C07C405/00; C07C405/0008; C07C405/0041; C07D307/937; C07D311/00; C07D311/02; C07D311/94
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
285 words
A compound of the formula ##STR33## wherein R 20 is ##STR34## wherein L is (1) --(CH 2 )d-C(R 2 ) 2 -- (2) --O--CH 2 --Y-- or (3) --CH═CH-- wherein d is zero to 5, R 2 is hydrogen, methyl, or fluoro, being the same or different with the proviso that one R 2 is not methyl when the other is fluoro, and Y is a valence bond, --CH 2 --, or --(CH 2 ) 2 --, wherein Q is ##STR35## wherein R 8 is hydrogen or alkyl of one to 4 carbon atoms, inclusive, wherein R 3 is (a) hydrogen, (b) alkyl of one to 12 carbon atoms, inclusive, (c) cycloalkyl of 3 to 10 carbon atoms, inclusive, (d) aralkyl of 7 to 12 carbon atoms, inclusive, (e) phenyl, (f) phenyl substituted with one, 2, or 3 chloro or alkyl of one to 4 carbon atoms, inclusive, ##STR36## wherein R 10 is phenyl, p-bromophenyl, p-biphenylyl, p-nitrophenyl, p-benzamidophenyl, or 2-naphthyl, and wherein R 11 is hydrogen or benzoyl, or (n) a pharmacologically acceptable cation, wherein R 60 is ##STR37## wherein C g H 2 .sbsb.g is alkylene of one to 9 carbon atoms, inclusive, with one to 5 carbon atoms, inclusive, in the chain between --CR 5 R 6 -- and terminal methyl, wherein R 5 and R 6 are hydrogen, alkyl of one to 4 carbon atoms, inclusive, or fluoro, being the same or different, with the proviso that one of R 5 and R 6 is fluoro only when the other is hydrogen or fluoro, wherein X is (1) trans-CH═CH-- (2) cis-CH═CH-- (3) --C.tbd.C-- or (4) --CH 2 CH 2 --, and wherein wavy line (˜) indicates attachment in alpha or beta configuration.
Claim 2
Dependent Claim
285 words
A compound of the formula ##STR33## wherein R 20 is ##STR34## wherein L is (1) --(CH 2 )d-C(R 2 ) 2 -- (2) --O--CH 2 --Y-- or (3) --CH═CH-- wherein d is zero to 5, R 2 is hydrogen, methyl, or fluoro, being the same or different with the proviso that one R 2 is not methyl when the other is fluoro, and Y is a valence bond, --CH 2 --, or --(CH 2 ) 2 --, wherein Q is ##STR35## wherein R 8 is hydrogen or alkyl of one to 4 carbon atoms, inclusive, wherein R 3 is (a) hydrogen, (b) alkyl of one to 12 carbon atoms, inclusive, (c) cycloalkyl of 3 to 10 carbon atoms, inclusive, (d) aralkyl of 7 to 12 carbon atoms, inclusive, (e) phenyl, (f) phenyl substituted with one, 2, or 3 chloro or alkyl of one to 4 carbon atoms, inclusive, ##STR36## wherein R 10 is phenyl, p-bromophenyl, p-biphenylyl, p-nitrophenyl, p-benzamidophenyl, or 2-naphthyl, and wherein R 11 is hydrogen or benzoyl, or (n) a pharmacologically acceptable cation, wherein R 60 is ##STR37## wherein C g H 2 .sbsb.g is alkylene of one to 9 carbon atoms, inclusive, with one to 5 carbon atoms, inclusive, in the chain between --CR 5 R 6 -- and terminal methyl, wherein R 5 and R 6 are hydrogen, alkyl of one to 4 carbon atoms, inclusive, or fluoro, being the same or different, with the proviso that one of R 5 and R 6 is fluoro only when the other is hydrogen or fluoro, wherein X is (1) trans-CH═CH-- (2) cis-CH═CH-- (3) --C.tbd.C-- or (4) --CH 2 CH 2 --, and wherein wavy line (˜) indicates attachment in alpha or beta configuration.
Claim 3
Dependent Claim
11 words
A compound according to claim 1 wherein R 20 is ##STR38##
Claim 4
Dependent Claim
11 words
A compound according to claim 1 wherein R 20 is ##STR39##
Claim 5
Dependent Claim
11 words
A compound according to claim 1 wherein R 20 is ##STR40##
Claim 6
Dependent Claim
11 words
A compound according to claim 1 wherein R 20 is ##STR41##
Claim 7
Dependent Claim
11 words
5-Keto-11-deoxy-PGF 1 α, methyl ester, a compound according to claim 5.
Claim 8
Dependent Claim
11 words
A compound according to claim 1 wherein R 20 is ##STR42##
Claim 9
Dependent Claim
11 words
A compound according to claim 1 wherein R 20 is ##STR43##
Claim 10
Dependent Claim
11 words
A compound according to claim 1 wherein R 20 is ##STR44##
Claim 11
Dependent Claim
41 words
A compound according to claim 9 wherein L is --(CH 2 )n, n being 2, 3, or 4, wherein Q is ##STR45## wherein R 8 is limited to hydrogen, methyl, or ethyl, and wherein R 4 is n-pentyl, 1,1-dimethylpentyl, or 1,1-difluoropentyl.
Claim 12
Dependent Claim
10 words
A compound according to claim 10 wherein X is --C.tbd.C--.
Claim 13
Dependent Claim
14 words
A compound according to claim 10 wherein X is --CH 2 CH 2 --.
Claim 14
Dependent Claim
9 words
5-Keto-13,14-dihydro-PGF 1 α, a compound according to claim 12.
Claim 15
Dependent Claim
11 words
5-Keto-13,14-dihydro-PGF 1 α, methyl ester, a compound according to claim 12.
Claim 16
Dependent Claim
9 words
5,15-Diketo-13,14-dihydro-PGF 1 α, a compound according to claim 12.
Claim 17
Dependent Claim
10 words
A compound according to claim 10 wherein X is trans--CH═CH--.
Claim 18
Dependent Claim
24 words
A compound according to claim 16 wherein R 3 is hydrogen, alkyl of one to 12 carbon atoms, inclusive, or a pharmacologically acceptable cation.
Claim 19
Dependent Claim
9 words
5-Keto-PGF 1 α, a compound according to claim 17.
Claim 20
Dependent Claim
11 words
5-Keto-PGF 1 α, methyl ester, a compound according to claim 17.
Claim 21
Dependent Claim
9 words
5,15-Diketo-PGF 1 α, a compound according to claim 17.
References Cited (Backward Citations)
US4131738A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-12-31 | 1983-07-02 | 1984-01-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-12-31 | 1987-07-02 | 1988-01-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-12-31 | 1991-07-02 | 1992-01-01 | $7700.00 | Window Closed / Lapsed |