← Back to Patent Explorer
US4458074A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for the preparation of 5,6,7,7a-tetrahydro-4H-thieno[3,2-c]pyridin-2-ones

Assignee: Sanofi SA
•
Filing: 1982-06-29
•
Granted: 1984-07-03
•
Expires: 2002-06-29
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract The present invention provides a process for the preparation of 5,6,7,7a-tetrahydro-4H-thieno[3,2-c]-pyridin-2-ones of the general formula: ##STR1## in which R is a hydrogen atom or a phenyl radical optionally substituted by at least one halogen atom, lower alkyl radical, lower alkoxy radical, nitro group, carboxyl group or alkoxycarbonyl radical, R' is a hydrogen atom or lower alkyl radical and n is 0 or a number of from 1 to 4, wherein a compound of the general formula: ##STR2## in which R, R' and n have the same meanings as above, is reacted with formaldehyde to give a compound of the general formula: ##STR3## in which R, R' and n have the same meanings as above, whereafter this compound is treated with dry hydrogen chloride to give the desired compound of general formula (I). The compounds are useful as anti-thrombotic agents.

Inventors

  • 👤 Andre Bouscuet
  • 👤 Alain Heymes

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 12:53
CPC Classifications
C; C07; C07D; C07D495/00; C07D495/02; C07D495/04; A; A61; A61P; A61P7/00; A61P7/02

Claims Analysis

Total Claims: 7
Claim 1
Independent Claim 95 words
A process for the preparation of a 5,6,7,7a-tetrahydro-4H-thieno [3,2-c]pyridin-2-one of the formula: ##STR10## in which R is a hydrogen atom, phenyl, or phenyl substituted by at least one halogen atom, lower alkyl radical, lower alkoxy radical, nitro group, carboxyl group or alkoxycarbonyl radical, R' is a hydrogen atom or lower alkyl radical, and n is 0 or an integer of from 1 to 4, which comprises reacting a compound of the formula: ##STR11## in which R, R' and n are as hereinbefore described, with formaldehyde, and then treating the resulting compound with dry hydrogen chloride.
Claim 2
Dependent Claim 95 words
A process for the preparation of a 5,6,7,7a-tetrahydro-4H-thieno [3,2-c]pyridin-2-one of the formula: ##STR10## in which R is a hydrogen atom, phenyl, or phenyl substituted by at least one halogen atom, lower alkyl radical, lower alkoxy radical, nitro group, carboxyl group or alkoxycarbonyl radical, R' is a hydrogen atom or lower alkyl radical, and n is 0 or an integer of from 1 to 4, which comprises reacting a compound of the formula: ##STR11## in which R, R' and n are as hereinbefore described, with formaldehyde, and then treating the resulting compound with dry hydrogen chloride.
Claim 3
Dependent Claim 24 words
A process according to claim 1, wherein the reaction between a compound of the formula (V) and formaldehyde is carried out at ambient temperature.
Claim 4
Dependent Claim 28 words
A process according to claim 1 or 2, wherein the reaction of the product of the first step with hydrogen chloride is carried out in an anhydrous medium.
Claim 5
Dependent Claim 17 words
A process according to claim 3, wherein the reaction is carried out in a polar, aprotic solvent.
Claim 6
Dependent Claim 22 words
A process according to claim 4, wherein the solvent is selected from the group consisting of dimethylformamide, dimethyl sulphoxide, N-methylpyrrolidone and N,N-dimethylacetamide.
Claim 7
Dependent Claim 17 words
A process according to claim 1 wherein the initial compound is N-(O-chlorobenzyl)-2-[5-tert.-butoxy-(thienyl-2)]-ethylamine and 5-(2-chlorobenzyl)-5,6,7,7a-tetrahydro-4H-thieno[3,2-c]-pyridin-2-one hydrochloride is prepared.

References Cited (Backward Citations)

FR53950E Cited
US4127580A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1987-07-03 1988-01-02 1988-07-03 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1991-07-03 1992-01-02 1992-07-03 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1995-07-03 1996-01-02 1996-07-03 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag