US4783483A
Expired / Lapsed
US
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Epoxides useful as antiallergic agents
Assignee: Ortho Pharmaceutical Corp
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Filing: 1986-12-29
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Granted: 1988-11-08
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Expires: 2006-12-29
Abstract
Abstract Alkenes of the formula (I) and epoxides (II) used to make them are useful as anti-inflammatory and antiallergic pharmaceuticals: ##STR1## wherein R 1 =H or CH 3 ; R 2 =phenyl, substituted phenyl, benzyl or a cysteinyl moiety; R 4 and R 5 =alkyl; n=O or 1; and R 3 is as described.
Inventors
- 👤 Michael P. Ferro
- 👤 Michael P. Wachter
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 21:31
CPC Classifications
C; C07; C07D; C07D303/00; C07D303/02; C07D303/12; C07D303/32; C07C; C07C323/00; C07D303/04; C07D303/14
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
100 words
An epoxide of the following formula (II): ##STR6## wherein R 1 is hydrogen or methyl; R 3 is --CH 2 CH 2 OH, --CH 2 CH 2 O(2-tetrahydropyranyl), --CH═C(CH 3 ) 2 or --CH(OR 5 ) 2 ; R 5 is lower alkyl; n is 0 or 1; a is a Z or E double bond when n is 0 and when n is 1, a is E; b is a Z or E double bond; and the hydrogen and R 1 moieties attached to the respective epoxy carbon atoms designated by an asterisk (*) are trans to each other.
Claim 2
Dependent Claim
100 words
An epoxide of the following formula (II): ##STR6## wherein R 1 is hydrogen or methyl; R 3 is --CH 2 CH 2 OH, --CH 2 CH 2 O(2-tetrahydropyranyl), --CH═C(CH 3 ) 2 or --CH(OR 5 ) 2 ; R 5 is lower alkyl; n is 0 or 1; a is a Z or E double bond when n is 0 and when n is 1, a is E; b is a Z or E double bond; and the hydrogen and R 1 moieties attached to the respective epoxy carbon atoms designated by an asterisk (*) are trans to each other.
Claim 3
Dependent Claim
20 words
The epoxide of claim 1, wherein the epoxy carbon atoms designated by an asterisk(*) are both of the R configuration.
Claim 4
Dependent Claim
20 words
The epoxide of claim 1, wherein the epoxy carbon atoms designated by an asterisk(*) are both of the S configuration.
Claim 5
Dependent Claim
50 words
The epoxide of claim 1, wherein said epoxide is a diasteriomeric pair of enantiomers, one of which is in the R and R configurations, respectively, at the two epoxy carbon atoms designated by an asterisk(*) while the other enantiomer is in the S and S configurations at such respective carbons.
Claim 6
Dependent Claim
57 words
The epoxide of claim 1, wherein R 1 is hydrogen or methyl; R 3 is --CH 2 CH 2 O(2-tetrahydropyranyl) or R 5 is methyl; n is 0 or 1; a is a Z or E double bond when n is 0 and when n is 1, a is E; and b is a Z double bond.
Claim 7
Dependent Claim
21 words
The epoxide of claim 1, wherein said epoxide is selected from the group consisting of: (3S,4S)-trans-3,4-epoxy-1-phenyl-8-(2-tetrahydropyranyloxy)-1(Z)-octene, (3S,4S)-trans-3,4-epoxy-1-phenyl-8-(2-tetrahydropyranyloxy)-1(E)-octene, (5S,6S)-1-phenyl-6,10-dimethyl-5,6-epoxy-transundeca-1(E),3(Z),9-triene, (3S,4S)-1-phenyl-4,8-dimethyl-trans-3,4-epoxy-nonacis-1(Z),7-diene, and (5RS,6RS)-trans-5,6-epoxy-9,9-dimethoxy-6-methyl-1-phenylnona-1(E),3(Z)-diene.
Claim 8
Dependent Claim
10 words
The epoxide of claim 1, wherein said epoxide is (3S,4S)-trans-3,4-epoxy-1-phenyl-8-(2-tetrahydropyranyloxy)1(Z)-octene.
Claim 9
Dependent Claim
10 words
The epoxide of claim 1, wherien said epoxide is (3S,4S)-trans-3,4-epoxy-1-phenyl-1-phenyl-8-(2-tetrahydropyranyloxy)1(E)-octene.
Claim 10
Dependent Claim
10 words
The epoxide of claim 1, wherein said epoxide is (5S,6S)-1-phenyl-6,10-dimethyl-5,6-epoxy-trans-undeca-(1E,3Z,9)-triene.
Claim 11
Dependent Claim
10 words
The epoxide of claim 1, wherein and epoxide is (3S,4S)-1-phenyl-4,8-diemthyl-trans-3,4-epoxy-nona-cis-(1Z,7)-diene.
Claim 12
Dependent Claim
10 words
The epoxide of claim 1, wherein said epoxide is (5RS,6RS)-trans-5,6-epoxy-9,9-diemthoxy-6-methyl-1-phenylnona(1E,3Z)-diene.
Claim 13
Dependent Claim
33 words
A pharmaceutical composition for the treatment of an allergic reaction in a mammal which comprises an anti-allergy effective amount of an epoxide of claim 1 in association with a pharmaceutically-acceptable diluent or carrier.
Claim 14
Dependent Claim
23 words
A method for the treatment of an allergic reaction in a mammal which comprises administering to the mammal, the composition of claim 12.
Claim 15
Dependent Claim
38 words
A method for the treatment of inflammation in a mammal which comprises administering to the mammal, a pharmaceutical composition which comprises a pharamceutically-effective amount of an epoxide of claim 1 in association with a pharmaceutically-acceptable diluent or carrier.
References Cited (Backward Citations)
US4513005A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-11-08 | 1992-05-09 | 1992-11-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-11-08 | 1996-05-09 | 1996-11-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-11-08 | 2000-05-09 | 2000-11-08 | $7700.00 | Window Closed / Lapsed |