US4123441A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Enlarged-hetero-ring prostacyclin analogs
Assignee: Pharmacia and Upjohn Co
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Filing: 1977-07-28
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Granted: 1978-10-31
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Expires: 1997-07-28
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
2026-11-04 15:05
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/77; C07D307/93; C07D307/935; C07D307/937; C07C; C07C405/00; C07D311/00; C07D311/02; C07D311/94
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
195 words
A 4Z compound of formula ##STR110## wherein L is --(CH 2 ) d --C (R 2 ) 2 -- 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, wherein Q is ##STR111## wherein R 8 is hydrogen or alkyl of one to 4 carbon atoms, inclusive, wherein R 59 is (a) hydrogen, (b) alkyl of one to 12 carbon atoms, inclusive, or (c) a pharmacologically acceptable cation; wherein R 4 is ##STR112## wherein C g H 2g 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; and wherein X is (1) trans--CH═CH-- (2) cis--CH═CH-- (3) --c═c-- or (4) --CH 2 CH 2 --; including the lower alkanoates thereof.
Claim 2
Dependent Claim
195 words
A 4Z compound of formula ##STR110## wherein L is --(CH 2 ) d --C (R 2 ) 2 -- 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, wherein Q is ##STR111## wherein R 8 is hydrogen or alkyl of one to 4 carbon atoms, inclusive, wherein R 59 is (a) hydrogen, (b) alkyl of one to 12 carbon atoms, inclusive, or (c) a pharmacologically acceptable cation; wherein R 4 is ##STR112## wherein C g H 2g 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; and wherein X is (1) trans--CH═CH-- (2) cis--CH═CH-- (3) --c═c-- or (4) --CH 2 CH 2 --; including the lower alkanoates thereof.
Claim 3
Dependent Claim
11 words
A compound according to claim 1 wherein R 20 is ##STR113##
Claim 4
Dependent Claim
11 words
A compound according to claim 1 wherein R 20 is ##STR114##
Claim 5
Dependent Claim
11 words
A compound according to claim 1 wherein R 20 is ##STR115##
Claim 6
Dependent Claim
11 words
A compound according to claim 1 wherein R 20 is ##STR116##
Claim 7
Dependent Claim
43 words
A compound according to claim 5 wherein L is --(CH 2 ) n --, n being 2, 3, or 4, wherein Q is ##STR117## 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 8
Dependent Claim
13 words
(4Z)-9-Deoxy-5,9α-epoxy-Δ 4 -11-deoxy-PGF 1 , methyl ester, a compound according to claim 6.
Claim 9
Dependent Claim
11 words
A compound according to claim 1 wherein R 20 is ##STR118##
Claim 10
Dependent Claim
11 words
A compound according to claim 1 wherein R 20 is ##STR119##
Claim 11
Dependent Claim
11 words
A compound according to claim 1 wherein R 20 is ##STR120##
Claim 12
Dependent Claim
41 words
A compound according to claim 10 wherein L is --(CH 2 ) n --, n being 2, 3, or 4, wherein Q is ##STR121## wherein R 8 is hydrogen, methyl, or ethyl, and wherein R 4 is n-pentyl, 1,1-dimethylpentyl, or 1,1-difluoropentyl.
Claim 13
Dependent Claim
10 words
A compound according to claim 11 wherein X is --C.tbd.C--.
Claim 14
Dependent Claim
14 words
A compound according to claim 11 wherein X is --CH 2 CH 2 --.
Claim 15
Dependent Claim
13 words
(4Z)-9-Deoxy-5,9α-epoxy-Δ 4 -13,14-dihydro-PGF 1 , methyl ester, a compound according to claim 13.
Claim 16
Dependent Claim
10 words
A compound according to claim 11 wherein X is trans--CH═CH--.
Claim 17
Dependent Claim
13 words
(4Z)-9-Deoxy-5,9α-epoxy-Δ 4 -PGF 1 , methyl ester, a compound according to claim 15.
Claim 18
Dependent Claim
13 words
(4Z)-9-Deoxy-5,9α-epoxy-Δ 4 -PGF 1 , sodium salt, a compound according to claim 15.
Claim 19
Dependent Claim
13 words
(4Z)-9-Deoxy-5,9α-epoxy-Δ 4 -PGF 1 , tetramethylammonium salt, a compound according to claim 15.
Claim 20
Dependent Claim
13 words
(4Z)-9-Deoxy-5,9α-epoxy-Δ 4 -15-keto-PGF 1 , methyl ester, a compound according to claim 15.
Claim 21
Dependent Claim
13 words
(4Z)-9-Deoxy-5,9α-epoxy-Δ 4 -15-deoxy-PGF 1 , methyl ester, a compound according to claim 10.
Claim 22
Dependent Claim
195 words
A 4E compound of the formula ##STR122## wherein L is --(CH 2 ) d --C (R 2 ) 2 -- 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, wherein Q is ##STR123## wherein R 8 is hydrogen or alkyl of one to 4 carbon atoms, inclusive, wherein R 59 is (a) hydrogen, (b) alkyl of one to 12 carbon atoms, inclusive, a pharmacologically acceptable cation; wherein R 4 is ##STR124## 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; and wherein X is (1) trans--CH═CH-- (2) cis--CH═CH-- (3) --c.tbd.c-- or (4) --CH 2 CH 2 --; including the lower alkanoates thereof.
Claim 23
Dependent Claim
195 words
A 4E compound of the formula ##STR122## wherein L is --(CH 2 ) d --C (R 2 ) 2 -- 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, wherein Q is ##STR123## wherein R 8 is hydrogen or alkyl of one to 4 carbon atoms, inclusive, wherein R 59 is (a) hydrogen, (b) alkyl of one to 12 carbon atoms, inclusive, a pharmacologically acceptable cation; wherein R 4 is ##STR124## 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; and wherein X is (1) trans--CH═CH-- (2) cis--CH═CH-- (3) --c.tbd.c-- or (4) --CH 2 CH 2 --; including the lower alkanoates thereof.
Claim 24
Dependent Claim
13 words
(4E)-9-Deoxy-5,9α-epoxy-Δ 4 -PGF 1 , methyl ester, a compound according to claim 21.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-10-30 | 1982-05-01 | 1982-10-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-10-30 | 1986-05-01 | 1986-10-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-10-30 | 1990-05-01 | 1990-10-31 | $7700.00 | Window Closed / Lapsed |