CS224634B2 - Method for producong a derivate of 5,6,7,7a-tetrahydro-4h-thieno-/3,2-c/pyridin-2-one - Google Patents
Method for producong a derivate of 5,6,7,7a-tetrahydro-4h-thieno-/3,2-c/pyridin-2-one Download PDFInfo
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- CS224634B2 CS224634B2 CS818683A CS868381A CS224634B2 CS 224634 B2 CS224634 B2 CS 224634B2 CS 818683 A CS818683 A CS 818683A CS 868381 A CS868381 A CS 868381A CS 224634 B2 CS224634 B2 CS 224634B2
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- formula
- compound
- acid
- compounds
- hydrogen
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- 238000000034 method Methods 0.000 title claims description 19
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 79
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 238000013329 compounding Methods 0.000 claims 1
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- 150000007524 organic acids Chemical class 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 21
- 239000000243 solution Substances 0.000 description 16
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- UMLDUMMLRZFROX-UHFFFAOYSA-N pyridin-2-ylboronic acid Chemical compound OB(O)C1=CC=CC=N1 UMLDUMMLRZFROX-UHFFFAOYSA-N 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 2
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- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
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- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
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- BDSNMIVGSVEKMH-UHFFFAOYSA-N 2-[(2-oxo-4,6,7,7a-tetrahydrothieno[3,2-c]pyridin-5-yl)methyl]benzonitrile Chemical compound C1C2=CC(=O)SC2CCN1CC1=CC=CC=C1C#N BDSNMIVGSVEKMH-UHFFFAOYSA-N 0.000 description 1
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- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 229940045860 white wax Drugs 0.000 description 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hematology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8025274A FR2495156A1 (fr) | 1980-11-28 | 1980-11-28 | Derives de la thieno-pyridinone, leur procede de preparation et leur application therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS224634B2 true CS224634B2 (en) | 1984-01-16 |
Family
ID=9248448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS818683A CS224634B2 (en) | 1980-11-28 | 1981-11-25 | Method for producong a derivate of 5,6,7,7a-tetrahydro-4h-thieno-/3,2-c/pyridin-2-one |
Country Status (36)
| Country | Link |
|---|---|
| US (1) | US4515951A (ko) |
| EP (1) | EP0054442B1 (ko) |
| JP (1) | JPS57120590A (ko) |
| KR (1) | KR870000824B1 (ko) |
| AR (1) | AR230285A1 (ko) |
| AT (1) | ATE9160T1 (ko) |
| AU (1) | AU559923B2 (ko) |
| BG (1) | BG36348A3 (ko) |
| CA (1) | CA1182458A (ko) |
| CS (1) | CS224634B2 (ko) |
| CY (1) | CY1281A (ko) |
| DD (1) | DD201903A5 (ko) |
| DE (1) | DE3165788D1 (ko) |
| DK (1) | DK152132C (ko) |
| ES (1) | ES507705A0 (ko) |
| FI (1) | FI72520C (ko) |
| FR (1) | FR2495156A1 (ko) |
| GR (1) | GR78021B (ko) |
| HK (1) | HK61685A (ko) |
| HU (1) | HU183711B (ko) |
| IE (1) | IE51709B1 (ko) |
| IL (1) | IL64146A (ko) |
| IN (1) | IN155340B (ko) |
| MA (1) | MA19331A1 (ko) |
| MY (1) | MY8600008A (ko) |
| NO (1) | NO155665C (ko) |
| NZ (1) | NZ199021A (ko) |
| OA (1) | OA06951A (ko) |
| PH (1) | PH23776A (ko) |
| PL (1) | PL129598B1 (ko) |
| PT (1) | PT73988B (ko) |
| RO (1) | RO83129B (ko) |
| SU (1) | SU1110385A3 (ko) |
| YU (1) | YU42448B (ko) |
| ZA (1) | ZA817874B (ko) |
| ZW (1) | ZW27481A1 (ko) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2528848A1 (fr) * | 1982-06-16 | 1983-12-23 | Sanofi Sa | Nouveau derive de thieno-pyridone, son procede de preparation et son application therapeutique |
| FR2576901B1 (fr) * | 1985-01-31 | 1987-03-20 | Sanofi Sa | Nouveaux derives de l'acide a-(oxo-2 hexahydro-2,4,5,6,7,7a thieno (3,2-c) pyridyl-5) phenyl acetique, leur procede de preparation et leur application therapeutique |
| FR2596392B1 (fr) * | 1986-03-27 | 1988-08-05 | Sanofi Sa | Derives de l'acide a-(hydroxy-3 oxo-2 hexahydro-2,4,5,6,7,7a thieno (3,2-c) pyridyl-5) phenylacetique, leur procede de preparation, leur application comme medicaments et les compositions les renfermant |
| ES2018860B3 (es) * | 1987-04-03 | 1991-05-16 | Cl Pharma | Nuevos derivados de 2 - acido acetico de tieniloxido, un procedimiento para su preparacion y el contenido en preparados farmaceuticos |
| FR2652579B1 (fr) * | 1989-10-02 | 1992-01-24 | Sanofi Sa | Derives d'hydroxy-2 thiophene et furanne condenses avec un cycle azote, sur procede de preparation et leur application en therapeutique. |
| JP2730319B2 (ja) * | 1991-04-26 | 1998-03-25 | 日本ビクター株式会社 | 磁気ディスク装置 |
| DE69526443T2 (de) * | 1994-10-07 | 2002-12-12 | Ube Industries | 2-silyloxy-tetrahydrothienopyridin, sein salz und verfahren zu seiner herstellung |
| NZ334389A (en) * | 1996-08-28 | 2001-05-25 | Ube Industries | Cyclic amine derivatives |
| CZ297570B6 (cs) * | 2000-12-25 | 2007-02-07 | Sankyo Company, Limited | Farmaceutický prípravek obsahující 2-acetoxypyridinový derivát a aspirin, které spolu pusobí v synergickém úcinku, kit jej obsahující a pouzití |
| US7557101B2 (en) * | 2006-12-08 | 2009-07-07 | Hoffman-La Roche Inc. | 4,5,6,7-tetrahydro-thieno[3,2-c] pyridine derivatives |
| WO2009066326A2 (en) * | 2007-11-19 | 2009-05-28 | Msn Laboratories Limited | Improved process for the preparation of prasugrel and its pharmaceutically acceptable salts |
| CN102241690B (zh) * | 2010-05-13 | 2015-08-12 | 天津药物研究院 | 一类含腈基的噻吩并吡啶酯类衍生物、其制备方法和用途 |
| CN101948479B (zh) * | 2010-09-29 | 2013-01-30 | 横店集团家园化工有限公司 | 普拉格雷中间体及其制备方法 |
| WO2012054535A2 (en) | 2010-10-18 | 2012-04-26 | Cerenis Therapeutics Sa | Compounds, compositions and methods useful for cholesterol mobilisation |
| CN108069981A (zh) * | 2016-11-14 | 2018-05-25 | 天津药物研究院有限公司 | 5-取代-4,5,6,7-四氢噻吩并[3,2-c]吡啶-2(4H)-酮的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2215948B1 (ko) * | 1973-02-01 | 1976-05-14 | Centre Etd Ind Pharma | |
| FR2345150A2 (fr) * | 1975-08-06 | 1977-10-21 | Centre Etd Ind Pharma | Nouveaux derives de la thienopyridine, et leur application |
| FR2495157A1 (fr) * | 1980-11-28 | 1982-06-04 | Sanofi Sa | Procede nouveau de preparation des tetrahydro-5, 6, 7, 7a 4h-thieno (3, 2-c) pyridinones-2 |
| FR2508459A1 (fr) * | 1981-06-30 | 1982-12-31 | Sanofi Sa | Procede de preparation de derives de la tetrahydro-5,6,7,7a 4h thieno (3,2-c) pyridinone-2 |
-
1980
- 1980-11-28 FR FR8025274A patent/FR2495156A1/fr active Granted
-
1981
- 1981-10-22 EP EP81401668A patent/EP0054442B1/fr not_active Expired
- 1981-10-22 AT AT81401668T patent/ATE9160T1/de not_active IP Right Cessation
- 1981-10-22 CY CY1281A patent/CY1281A/xx unknown
- 1981-10-22 DE DE8181401668T patent/DE3165788D1/de not_active Expired
- 1981-10-28 IL IL64146A patent/IL64146A/xx not_active IP Right Cessation
- 1981-11-06 IN IN1235/CAL/81A patent/IN155340B/en unknown
- 1981-11-11 PH PH26485A patent/PH23776A/en unknown
- 1981-11-11 ZW ZW274/81A patent/ZW27481A1/xx unknown
- 1981-11-12 AU AU77429/81A patent/AU559923B2/en not_active Ceased
- 1981-11-13 PT PT73988A patent/PT73988B/pt not_active IP Right Cessation
- 1981-11-13 ZA ZA817874A patent/ZA817874B/xx unknown
- 1981-11-13 MA MA19535A patent/MA19331A1/fr unknown
- 1981-11-14 OA OA57547A patent/OA06951A/xx unknown
- 1981-11-16 ES ES507705A patent/ES507705A0/es active Granted
- 1981-11-17 GR GR66543A patent/GR78021B/el unknown
- 1981-11-17 IE IE2683/81A patent/IE51709B1/en not_active IP Right Cessation
- 1981-11-18 AR AR287457A patent/AR230285A1/es active
- 1981-11-19 BG BG8154209A patent/BG36348A3/xx unknown
- 1981-11-20 NZ NZ199021A patent/NZ199021A/en unknown
- 1981-11-23 FI FI813730A patent/FI72520C/fi not_active IP Right Cessation
- 1981-11-24 DK DK520781A patent/DK152132C/da not_active IP Right Cessation
- 1981-11-25 CS CS818683A patent/CS224634B2/cs unknown
- 1981-11-26 PL PL1981233979A patent/PL129598B1/pl unknown
- 1981-11-27 YU YU2790/81A patent/YU42448B/xx unknown
- 1981-11-27 SU SU813357149A patent/SU1110385A3/ru active
- 1981-11-27 DD DD81235201A patent/DD201903A5/de not_active IP Right Cessation
- 1981-11-27 CA CA000391052A patent/CA1182458A/en not_active Expired
- 1981-11-27 RO RO105882A patent/RO83129B/ro unknown
- 1981-11-27 NO NO814055A patent/NO155665C/no unknown
- 1981-11-27 KR KR1019810004596A patent/KR870000824B1/ko active
- 1981-11-27 JP JP56190447A patent/JPS57120590A/ja active Granted
- 1981-11-27 HU HU813559A patent/HU183711B/hu not_active IP Right Cessation
-
1984
- 1984-07-25 US US06/635,461 patent/US4515951A/en not_active Expired - Lifetime
-
1985
- 1985-08-15 HK HK616/85A patent/HK61685A/xx not_active IP Right Cessation
-
1986
- 1986-12-30 MY MY8/86A patent/MY8600008A/xx unknown
Also Published As
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