Patent US3496162A successfully refreshed from Google Patents.
Patent US4218436A successfully refreshed from Google Patents.
US4218436A
Expired / Lapsed
US
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Compounds and methods
Assignee: Pharmacia and Upjohn Co
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Filing: 1979-04-26
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Granted: 1980-08-19
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Expires: 1999-04-26
Abstract
Abstract A method for the radioimmunoassay of PGE 1 -type and PGE 2 -type compounds and PGX is disclosed which utilizes antibodies formed against a prostaglandin mimic. Conjugates are disclosed which are formed by attaching a prostaglandin mimic to a carrier molecule. Antibodies are disclosed which are specific against PGE 1 -type and PGE 2 -type compounds, PGH 2 , and PGX. Complexes are disclosed which are formed by binding an antibody raised against a prostaglandin mimic with its corresponding authentic prostaglandin.
Inventors
- 👤 Francis A. Fitzpatrick
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 00:43
CPC Classifications
G; G01; G01N; G01N33/00; G01N33/48; G01N33/50; G01N33/88; A; A61; A61K; A61K47/00; A61K47/50; A61K47/51; A61K47/68; A61K47/6801; A61K47/6803; C; C07; C07K; C07K16/00; C07K16/18; C07K16/26; Y; Y10; Y10S; Y10S436/00; Y10S436/804; Y10S436/815; Y10S436/823; Y10S530/00; Y10S530/806
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
307 words
An antibody extracted from a mammal or bird after innoculation with a conjugate formed from a carrier molecule selected from the group natural protein, synthetic polypeptide, and other macromolecular immunogen of molecular weight greater than 2,000 and less than 500,000 and a compound selected from the group ##STR26## wherein M 1 is ##STR27## wherein R 5 is hydrogen or methyl; wherein L 1 is ##STR28## or a mixture of ##STR29## wherein R 3 and R 4 are hydrogen, methyl, or fluoro, being the same or different, with the proviso that one of R 3 and R 4 is fluoro only when the other is hydrogen or fluoro; wherein Z 1 is (1) cis--CH═CH--CH 2 --(CH 2 )g--CH 2 --, (2) cis--CH═CH--CH 2 --(CH 2 )g--CF 2 --, (3) cis--CH 2 --CH═CH--(CH 2 )g--CH 2 --, (4) --(CH 2 ) 3 --(CH 2 )g--CH 2 --, (5) --(CH 2 ) 3 --(CH 2 )g--CF 2 --, (6) --CH 2 --O--CH 2 --(CH 2 )g--CH 2 --, (7) --C═C--CH 2 --(CH 2 )g--CH 2 --, (8) --CH 2 --C═C--(CH 2 )g--CH 2 --, ##STR30## wherein g is one, 2, or 3; wherein R 7 is ##STR31## wherein m is one to 5, inclusive; n is zero or one; T is chloro, fluoro, trifluoromethyl, alkyl of one to 3 carbon atoms, inclusive, or alkoxy of one to 3 carbon atoms, inclusive; and s is zero, one, 2 or 3, the various T's being the same or different, with the proviso that not more than two T's are other than alkyl, with the further proviso that R 7 is ##STR32## wherein T and s are as defined above, only when R 3 and R 4 are hydrogen or methyl, being the same or different; and wherein X 1 is --COOR 1 wherein R 1 is hydrogen or a pharmacologically acceptable cation.
Claim 2
Dependent Claim
307 words
An antibody extracted from a mammal or bird after innoculation with a conjugate formed from a carrier molecule selected from the group natural protein, synthetic polypeptide, and other macromolecular immunogen of molecular weight greater than 2,000 and less than 500,000 and a compound selected from the group ##STR26## wherein M 1 is ##STR27## wherein R 5 is hydrogen or methyl; wherein L 1 is ##STR28## or a mixture of ##STR29## wherein R 3 and R 4 are hydrogen, methyl, or fluoro, being the same or different, with the proviso that one of R 3 and R 4 is fluoro only when the other is hydrogen or fluoro; wherein Z 1 is (1) cis--CH═CH--CH 2 --(CH 2 )g--CH 2 --, (2) cis--CH═CH--CH 2 --(CH 2 )g--CF 2 --, (3) cis--CH 2 --CH═CH--(CH 2 )g--CH 2 --, (4) --(CH 2 ) 3 --(CH 2 )g--CH 2 --, (5) --(CH 2 ) 3 --(CH 2 )g--CF 2 --, (6) --CH 2 --O--CH 2 --(CH 2 )g--CH 2 --, (7) --C═C--CH 2 --(CH 2 )g--CH 2 --, (8) --CH 2 --C═C--(CH 2 )g--CH 2 --, ##STR30## wherein g is one, 2, or 3; wherein R 7 is ##STR31## wherein m is one to 5, inclusive; n is zero or one; T is chloro, fluoro, trifluoromethyl, alkyl of one to 3 carbon atoms, inclusive, or alkoxy of one to 3 carbon atoms, inclusive; and s is zero, one, 2 or 3, the various T's being the same or different, with the proviso that not more than two T's are other than alkyl, with the further proviso that R 7 is ##STR32## wherein T and s are as defined above, only when R 3 and R 4 are hydrogen or methyl, being the same or different; and wherein X 1 is --COOR 1 wherein R 1 is hydrogen or a pharmacologically acceptable cation.
Claim 3
Dependent Claim
31 words
The antibody of claim 1 where the carrier molecule is selected from the group mammal or bird albumin, mammal or bird globulin, poly-1-lysine, and polypeptide of molecular weight greater than 2500.
Claim 4
Dependent Claim
17 words
The antibody of claim 2 where the carrier molecule is keyhole limpet hemocyanin or bovine serum albumin.
Claim 5
Dependent Claim
46 words
An antibody of claim 1 where the mimic is of a PGE-type compound and the serum extracted, at a dilution of at least 1:100, binds at least 25% of the radiolabeled form of the authentic PG corresponding to the hapten used and to elicit the antibody.
Claim 6
Dependent Claim
30 words
The antibody of claim 4 where the serum extracted, at a dilution by volume of at least 1:100, binds at least 50±3% of the radiolabeled form of the authentic PG.
Claim 7
Dependent Claim
12 words
The antibody of claim 5 wherein the dilution is at least 1:1000.
Claim 8
Dependent Claim
15 words
The antibody of claim 5 wherein the PG mimic is a 9-deoxy-9-methylene-PGF 1 -type compound.
Claim 9
Dependent Claim
15 words
The antibody of claim 5 where the PG mimic is a 9-deoxy-9-methylene-PGF 2 -type compound.
Claim 10
Dependent Claim
15 words
The antibody of claim 5 where the PG mimic is a compound of Formula V.
Claim 11
Dependent Claim
15 words
The antibody of claim 9 where the PG mimic is a 9-deoxy-9-methylene-PGF 1 -type compound.
Claim 12
Dependent Claim
13 words
The antibody of claim 10 where the PG mimic is 9-deoxy-9-methylene-PGF 1 .
Claim 13
Dependent Claim
15 words
The antibody of claim 9 where the PG mimic is a 9-deoxy-9-methylene-PGF 2 -type compound.
Claim 14
Dependent Claim
14 words
The antibody of claim 12 where the PG mimic is 9-deoxy-9-methylene PGF 2 .
Claim 15
Dependent Claim
13 words
The antibody of claim 12 where the PG mimic is 9-deoxy-9-methylene-15(R)-15-methyl-PGF 2 .
Claim 16
Dependent Claim
13 words
The antibody of claim 12 where the PG mimic is 9-deoxy-9-methylene-15(S)-15-methyl-PGF 2 .
Claim 17
Dependent Claim
43 words
The antibody of claim 2 where the PG mimic is (5Z,9α,11α,13E,15S)-9,11-azo-15-hydroxyprosta-5,13-dien-1-oic acid and no more than 100 μl. of the serum extracted delays platelet aggregation (1.0 ml. PRP; 400 μg. arachidonic acid) for 1 minute at the midpoint of the maximum aggregatory response.
Claim 18
Dependent Claim
15 words
The antibody of claim 16 where no more than 50 μl. of antiserum delays aggregation.
Claim 19
Dependent Claim
44 words
The antibody of claim 2 where the PG mimic is 9-deoxy-6,9α-epoxy-PGF 1 α and no more than 50 μl. of the serum extracted restores the platelet aggregation (2.0 ml. PRP; 1000 μg. arachidonic acid) blocked by 0.050 μg. PGX in less than 10 minutes.
Claim 20
Dependent Claim
16 words
The antibody of claim 18 where no more than 30 μl. of the antiserum restores aggregation.
Claim 21
Dependent Claim
26 words
A complex formed by binding an antibody raised against a PG mimic of formula II, III, or IV of claim 1 with its corresponding authentic prostaglandin.
Claim 22
Dependent Claim
14 words
The complex of claim 20 where the mimic is a compound of formula IV.
Claim 23
Dependent Claim
14 words
The complex of claim 21 where the mimic is a 9-deoxy-9-methylene-PGF 1 -type compound.
Claim 24
Dependent Claim
14 words
The complex of claim 21 where the mimic is a 9-deoxy-9-methylene-PGF 2 -type compound.
Claim 25
Dependent Claim
14 words
The complex of claim 21 where the mimic is a compound of formula V.
Claim 26
Dependent Claim
14 words
The complex of claim 24 where the mimic is a 9-deoxy-9-methylene-PGF 1 -type compound.
Claim 27
Dependent Claim
12 words
The complex of claim 25 where the mimic is 9-deoxy-9-methylene-PGF 1 .
Claim 28
Dependent Claim
14 words
The complex of claim 24 where the mimic is a 9-deoxy-9-methylene-PGF 2 -type compound.
Claim 29
Dependent Claim
12 words
The complex of claim 27 where the mimic is 9-deoxy-9-methylene-PGF 2 .
Claim 30
Dependent Claim
13 words
The complex of claim 27 where the mimic is 9-deoxy-9-methylene-15(R)-15-methyl PGF 2 .
Claim 31
Dependent Claim
14 words
The complex of claim 27 where the PG mimic is 9-deoxy-9-methylene-15(S)-15-methyl PGF 2 .
Claim 32
Dependent Claim
11 words
The complex of claim 20 where the mimic is (5Z,9α,11α,13E,15S)-9,11-azo-15-hydroxyprosta-5,13-dien-1-oic acid.
Claim 33
Dependent Claim
12 words
The complex of claim 20 where the mimic is 9-deoxy-6,9α-epoxy-PGF 1 α.
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) | 1983-08-19 | 1984-02-18 | 1984-08-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-08-19 | 1988-02-18 | 1988-08-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-08-19 | 1992-02-18 | 1992-08-19 | $7700.00 | Window Closed / Lapsed |