US4740510A
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US
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Derivatives of alpha-(2-oxo 2,4,5,6,7,7a-hexahydro thieno[3,2-c]5-pyridyl) phenyl acetic acid, and their use as platelet and thrombotic aggregation inhibitors
Assignee: Elf Sanofi SA
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Filing: 1986-01-31
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Granted: 1988-04-26
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Expires: 2006-01-31
Abstract
Abstract The present invention relates to novel derivatives of alpha-(2-oxo 2,4,5,6,7,7a-hexahydro thieno [3,2-c] 5-pyridyl) phenyl acetic acid corresponding to the following general formula: <IMAGE> their addition salts with pharmaceutically-acceptable inorganic or organic acids as well as isomers and their mixtures. The invention also relates to their process of preparation and to medicaments containing these compounds which are of therapeutic use as inhibitors of platelet- and thrombotic-aggregation.
Inventors
- 👤 Alain Badorc
- 👤 Daniel Frehel
- 👤 Jean-Pierre Maffrand
- 👤 Eric Vallee
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 07:21
CPC Classifications
C; C07; C07D; C07D495/00; C07D495/02; C07D495/04; A; A61; A61P; A61P7/00; A61P7/02
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
237 words
A compound of the formula ##STR26## in which Y represents hydroxyl (--OH): or Y represents (--OR) in which R is a linear or branched C 1 -C 4 alkyl radical or a benzyl or phenylethyl radical, or a phenyl- substituted benzyl of phenylethyl radical, or a dialkyl amino group of the formula: ##STR27## in which n represents a whole number from 0 to 4, R 1 and R 2 are each a C 1 -C 4 alkyl radical or Y represents an amino group of the formula ##STR28## in which R 3 and R 4 may be the same or different and are each hydrogen or a linear or branched C 1 -C 4 alkyl group, a phenyl, benzyl, phenylthyl, substituted benzyl or substituted phenylethyl group, a (3-pyridyl) methyl or (4-pyridyl) methyl group, or R 3 and R 4 from together with the nitrogn atom to which they are attached, a pyrrolidiono or morpholino group, these being unsubstituted or substituted by C 1 -C 4 alkyl radical, a phenyl radical, or a phenyl radical substituted by at least one member of the group consisting of halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or trifluoromethyl; where X represent hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, trifluoromethyl, nitro, cyano, carboxy or a C 1 -C 4 alkoxy carbonyl; and the acid addition salts with pharmaceutically acceptable inorganic and organic acids.
Claim 2
Dependent Claim
237 words
A compound of the formula ##STR26## in which Y represents hydroxyl (--OH): or Y represents (--OR) in which R is a linear or branched C 1 -C 4 alkyl radical or a benzyl or phenylethyl radical, or a phenyl- substituted benzyl of phenylethyl radical, or a dialkyl amino group of the formula: ##STR27## in which n represents a whole number from 0 to 4, R 1 and R 2 are each a C 1 -C 4 alkyl radical or Y represents an amino group of the formula ##STR28## in which R 3 and R 4 may be the same or different and are each hydrogen or a linear or branched C 1 -C 4 alkyl group, a phenyl, benzyl, phenylthyl, substituted benzyl or substituted phenylethyl group, a (3-pyridyl) methyl or (4-pyridyl) methyl group, or R 3 and R 4 from together with the nitrogn atom to which they are attached, a pyrrolidiono or morpholino group, these being unsubstituted or substituted by C 1 -C 4 alkyl radical, a phenyl radical, or a phenyl radical substituted by at least one member of the group consisting of halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or trifluoromethyl; where X represent hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, trifluoromethyl, nitro, cyano, carboxy or a C 1 -C 4 alkoxy carbonyl; and the acid addition salts with pharmaceutically acceptable inorganic and organic acids.
Claim 3
Dependent Claim
16 words
An addition salt of a compound of claim 1 with a pharmaceutically-acceptable inorganic or organic acid.
Claim 4
Dependent Claim
13 words
A mixture of at least two isomers of a compound of claim 1.
Claim 5
Dependent Claim
8 words
Methyl alpha-(2-oxo 2,4,5,6,7,7a-hexahydro thieno [3,2-c] 5-pyridyl) (2-chloro phenyl)-acetate.
Claim 6
Dependent Claim
8 words
Methyl alpha-(2-oxo 2,4,5,6,7,7a-hexahydro thieno [3,2-c] 5-pyridyl) (2-chloro phenyl)-acetate.
Claim 7
Dependent Claim
7 words
Methyl alpha-(2-oxo 2,4,5,6,7,7a-hexahydro thieno [3,2-c] 5-pyridyl) phenyl-acetate.
Claim 8
Dependent Claim
7 words
Methyl alpha-(2-oxo 2,4,5,6,7,7a-hexahydro thieno [3,2-c] 5-pyridyl) phenyl-acetate.
Claim 9
Dependent Claim
8 words
Methyl alpha-(2-oxo 2,4,5,6,7,7a-hexahydro thieno [3,2-c] 5-pyridyl) (2-fluoro phenyl)-acetate.
Claim 10
Dependent Claim
8 words
Methyl alpha-(2-oxo 2,4,5,6,7,7a-hexahydro thieno [3,2-c] 5-pyridyl) (2-fluoro phenyl)-acetate.
Claim 11
Dependent Claim
8 words
Ethyl alpha-(2-oxo 2,4,5,6,7,7a-hexahydro thieno [3,2-c] 5-pyridyl) (2-chloro phenyl)-acetate.
Claim 12
Dependent Claim
8 words
Ethyl alpha-(2-oxo 2,4,5,6,7,7a-hexahydro thieno [3,2-c] 5-pyridyl) (2-chloro phenyl)-acetate.
Claim 13
Dependent Claim
8 words
Ethyl alpha-(2-oxo 2,4,5,6,7,7a-hexahydro thieno [3,2-c] 5-pyridyl) (2-methyl phenyl)-acetate.
Claim 14
Dependent Claim
8 words
Ethyl alpha-(2-oxo 2,4,5,6,7,7a-hexahydro thieno [3,2-c] 5-pyridyl) (2-methyl phenyl)-acetate.
Claim 15
Dependent Claim
8 words
Isopropyl alpha-(2-oxo 2,4,5,6,7,7a-hexahydro thieno [3,2-c] 5-pyridyl) (2-chloro phenyl)-acetate.
Claim 16
Dependent Claim
8 words
Isopropyl alpha-(2-oxo 2,4,5,6,7,7a-hexahydro thieno [3,2-c] 5-pyridyl) (2-chloro phenyl)-acetate.
Claim 17
Dependent Claim
8 words
Tert-butyl alpha-(2-oxo 2,4,5,6,7,7a-hexahydro thieno [3,2-c] 5-pyridyl (2-chloro phenyl)-acetate.
Claim 18
Dependent Claim
8 words
Tert-butyl alpha-(2-oxo 2,4,5,6,7,7a-hexahydro thieno [3,2-c] 5-pyridyl (2-chloro phenyl)-acetate.
Claim 19
Dependent Claim
9 words
N alpha-(2-oxo 2,4,5,6,7,7a-hexahydro thieno [3,2-c] 5-pyridyl) (2-chloro phenyl)-acetyl pyrrolidine.
Claim 20
Dependent Claim
9 words
N alpha-(2-oxo 2,4,5,6,7,7a-hexahydro thieno [3,2-c] 5-pyridyl) (2-chloro phenyl)-acetyl pyrrolidine.
Claim 21
Dependent Claim
8 words
N,N-dimethyl alpha-(2-oxo 2,4,5,6,7,7a-hexahydro thieno [3,2-c] 5-pyridyl) (2-chloro phenyl)-acetamide.
Claim 22
Dependent Claim
8 words
N,N-dimethyl alpha-(2-oxo 2,4,5,6,7,7a-hexahydro thieno [3,2-c] 5-pyridyl) (2-chloro phenyl)-acetamide.
Claim 23
Dependent Claim
7 words
Alpha-(2-oxo 2,4,5,6,7,7a-hexahydro thieno [3,2-c]5-pyridyl) (2-chloro phenyl)-acetic acid.
Claim 24
Dependent Claim
7 words
Alpha-(2-oxo 2,4,5,6,7,7a-hexahydro thieno [3,2-c]5-pyridyl) (2-chloro phenyl)-acetic acid.
Claim 25
Dependent Claim
59 words
A platelet- and thromboticaggregation-inhibition composition, comprising as the active ingredient, in an amount effective thereof, a compound according to formula (I), or an acid addition salt of a compound according to formula (I) with a pharmaceutically- acceptable inorganic or organic acid, or a mixture of two or more isomers according to formula (I), together with a pharmaceutically acceptable carrier.
Claim 26
Dependent Claim
59 words
A platelet- and thromboticaggregation-inhibition composition, comprising as the active ingredient, in an amount effective thereof, a compound according to formula (I), or an acid addition salt of a compound according to formula (I) with a pharmaceutically- acceptable inorganic or organic acid, or a mixture of two or more isomers according to formula (I), together with a pharmaceutically acceptable carrier.
Claim 27
Dependent Claim
17 words
The composition according to claim 14, in a dosage form suitable for oral, parenteral or rectal administration.
Claim 28
Dependent Claim
25 words
The composition according to claim 14 or 15, in the form of a unit dose containing 0.005 g to 0.250 g of the active ingredient.
References Cited (Backward Citations)
US4424356A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-04-26 | 1991-10-26 | 1992-04-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-04-26 | 1995-10-26 | 1996-04-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-04-26 | 1999-10-26 | 2000-04-26 | $7700.00 | Window Closed / Lapsed |