ES8102130A1 - 5-2-Chlorobenzyl-4,5,6,7-tetra-thieno(3,2-c) pyridine prepn. - by reaction of tetra:hydro:thieno:pyridine with 2-chlorobenzyl alcohol or 2-chloro:benzaldehyde using hydrogenation catalyst - Google Patents
5-2-Chlorobenzyl-4,5,6,7-tetra-thieno(3,2-c) pyridine prepn. - by reaction of tetra:hydro:thieno:pyridine with 2-chlorobenzyl alcohol or 2-chloro:benzaldehyde using hydrogenation catalystInfo
- Publication number
- ES8102130A1 ES8102130A1 ES488694A ES488694A ES8102130A1 ES 8102130 A1 ES8102130 A1 ES 8102130A1 ES 488694 A ES488694 A ES 488694A ES 488694 A ES488694 A ES 488694A ES 8102130 A1 ES8102130 A1 ES 8102130A1
- Authority
- ES
- Spain
- Prior art keywords
- pyridine
- chlorobenzyl
- thieno
- tetra
- prepn
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000006243 chemical reaction Methods 0.000 title abstract 3
- MBYQPPXEXWRMQC-UHFFFAOYSA-N (2-chlorophenyl)methanol Chemical compound OCC1=CC=CC=C1Cl MBYQPPXEXWRMQC-UHFFFAOYSA-N 0.000 title abstract 2
- 239000003054 catalyst Substances 0.000 title abstract 2
- 238000005984 hydrogenation reaction Methods 0.000 title abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 title 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 title 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 title 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title 1
- OGUWOLDNYOTRBO-UHFFFAOYSA-N 4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1NCCC2=C1C=CS2 OGUWOLDNYOTRBO-UHFFFAOYSA-N 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 2
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 abstract 1
- 101000783577 Dendroaspis angusticeps Thrombostatin Proteins 0.000 abstract 1
- 101000783578 Dendroaspis jamesoni kaimosae Dendroaspin Proteins 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 229940127218 antiplatelet drug Drugs 0.000 abstract 1
- 210000001772 blood platelet Anatomy 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 abstract 1
- PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 abstract 1
- 229940124549 vasodilator Drugs 0.000 abstract 1
- 239000003071 vasodilator agent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Abstract
Process for the prepn. of 5-(2-chlorobenzyl)-4,5,6,7-tetrahydrothieno(3,2-c)pyridine (I) by reaction of 4,5,6,7-tetrahydrothieno(3,2-c)pyridine (II) with 2-chlorobenzyl alcohol (III) in the presence of a hydrogenation catalyst above room temp. or by reaction of (II) with 2-chlorobenzaldehyde (IV) in the presence of Raney Nickel and hydrogen at 120-140 degrees C. (I) is known antiinflammatory, vasodilator and blood platelet aggregation inhibitor. Present methods of prepn. give poor yields and/or use dangerous or costly reagents.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT19831/79A IT1166580B (en) | 1979-02-02 | 1979-02-02 | PROCESS FOR PREPARATION OF 5- (2-CHLOROBENZYL) -4,5,6,7-TETRAHYDROTHIEN (3,2-C) PYRIDIN |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES8102130A1 true ES8102130A1 (en) | 1980-12-16 |
| ES488694A0 ES488694A0 (en) | 1980-12-16 |
Family
ID=11161641
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES488694A Granted ES488694A0 (en) | 1979-02-02 | 1980-01-25 | PROCEDURE FOR THE PREPARATION OF 5- (2-CHLOROBENCIL) -4,5,6,7-TETRAHYDROTIENE (3,2, C) PIRIDINE |
Country Status (8)
| Country | Link |
|---|---|
| AR (1) | AR222686A1 (en) |
| AT (1) | AT372089B (en) |
| BE (1) | BE881360A (en) |
| DE (1) | DE3000888A1 (en) |
| ES (1) | ES488694A0 (en) |
| FR (1) | FR2447923A1 (en) |
| IT (1) | IT1166580B (en) |
| PT (1) | PT70767A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6185391A (en) * | 1984-10-03 | 1986-04-30 | Nisshin Flour Milling Co Ltd | Preparation of 5-(2-chlorobenzyl)-4,5,6,7-tetra-hydrothieno (3,2-c) pyridine |
| EP0573975A1 (en) * | 1992-06-08 | 1993-12-15 | Fuji Photo Film Co., Ltd. | 2-alkoxycarbonyl-5-o-chlorobenzyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine derivative and process for producing the same |
-
1979
- 1979-02-02 IT IT19831/79A patent/IT1166580B/en active
-
1980
- 1980-01-11 DE DE19803000888 patent/DE3000888A1/en active Granted
- 1980-01-23 FR FR8001440A patent/FR2447923A1/en active Granted
- 1980-01-24 AT AT0036880A patent/AT372089B/en not_active IP Right Cessation
- 1980-01-25 ES ES488694A patent/ES488694A0/en active Granted
- 1980-01-28 BE BE2/58368A patent/BE881360A/en not_active IP Right Cessation
- 1980-01-30 AR AR279806A patent/AR222686A1/en active
- 1980-02-01 PT PT70767A patent/PT70767A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATA36880A (en) | 1983-01-15 |
| AR222686A1 (en) | 1981-06-15 |
| FR2447923B1 (en) | 1983-06-24 |
| FR2447923A1 (en) | 1980-08-29 |
| AT372089B (en) | 1983-08-25 |
| DE3000888C2 (en) | 1988-11-17 |
| IT7919831A0 (en) | 1979-02-02 |
| DE3000888A1 (en) | 1980-08-07 |
| PT70767A (en) | 1980-03-01 |
| BE881360A (en) | 1980-05-16 |
| ES488694A0 (en) | 1980-12-16 |
| IT1166580B (en) | 1987-05-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD1A | Patent lapsed |
Effective date: 19960603 |