CA1126732A - Thieno(3,2-c)- and thieno(2,3-c)pyridines, process for their preparation and therapeutic composition containing them - Google Patents
Thieno(3,2-c)- and thieno(2,3-c)pyridines, process for their preparation and therapeutic composition containing themInfo
- Publication number
- CA1126732A CA1126732A CA321,393A CA321393A CA1126732A CA 1126732 A CA1126732 A CA 1126732A CA 321393 A CA321393 A CA 321393A CA 1126732 A CA1126732 A CA 1126732A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- thieno
- formula
- alkyl
- derivative
- 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
- 238000000034 method Methods 0.000 title claims description 48
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000000203 mixture Substances 0.000 title description 6
- 230000001225 therapeutic effect Effects 0.000 title description 5
- 150000003222 pyridines Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- -1 alkyl chloroformate Chemical compound 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 229940125670 thienopyridine Drugs 0.000 claims description 3
- 239000002175 thienopyridine Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- 125000006177 alkyl benzyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
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- 229960003965 antiepileptics Drugs 0.000 abstract description 4
- GDQBPBMIAFIRIU-UHFFFAOYSA-N thieno[2,3-c]pyridine Chemical class C1=NC=C2SC=CC2=C1 GDQBPBMIAFIRIU-UHFFFAOYSA-N 0.000 abstract 1
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- 239000013078 crystal Substances 0.000 description 35
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
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- 241001465754 Metazoa Species 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- SAALQYKUFCIMHR-UHFFFAOYSA-N propan-2-ol;2-propan-2-yloxypropane Chemical compound CC(C)O.CC(C)OC(C)C SAALQYKUFCIMHR-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
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- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 3
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- 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
- 238000011282 treatment Methods 0.000 description 3
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- IMAWRJZYXYLGBL-UHFFFAOYSA-N 2-methoxy-1-phenylpiperazine Chemical compound COC1CNCCN1C1=CC=CC=C1 IMAWRJZYXYLGBL-UHFFFAOYSA-N 0.000 description 2
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- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
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- 125000003710 aryl alkyl group Chemical group 0.000 description 2
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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- TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 2
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- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 231100000048 toxicity data Toxicity 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Rheumatology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7804561 | 1978-02-17 | ||
| FR7804561A FR2417512A1 (fr) | 1978-02-17 | 1978-02-17 | Thieno (3,2-c) et thieno (2,3-c) pyridines, leur procede de preparation et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1126732A true CA1126732A (en) | 1982-06-29 |
Family
ID=9204729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA321,393A Expired CA1126732A (en) | 1978-02-17 | 1979-02-13 | Thieno(3,2-c)- and thieno(2,3-c)pyridines, process for their preparation and therapeutic composition containing them |
Country Status (31)
| Country | Link |
|---|---|
| EP (1) | EP0003920B1 (en:Method) |
| JP (1) | JPS54157599A (en:Method) |
| AR (1) | AR227623A1 (en:Method) |
| AT (1) | AT369369B (en:Method) |
| AU (1) | AU519318B2 (en:Method) |
| BE (1) | BE874228A (en:Method) |
| CA (1) | CA1126732A (en:Method) |
| CH (1) | CH635844A5 (en:Method) |
| DD (1) | DD142053A5 (en:Method) |
| DE (1) | DE2960109D1 (en:Method) |
| DK (1) | DK146046C (en:Method) |
| ES (1) | ES477401A1 (en:Method) |
| FI (1) | FI66872C (en:Method) |
| FR (1) | FR2417512A1 (en:Method) |
| GB (1) | GB2014576B (en:Method) |
| GR (1) | GR66844B (en:Method) |
| HU (1) | HU178075B (en:Method) |
| IE (1) | IE47789B1 (en:Method) |
| IL (1) | IL56541A (en:Method) |
| IT (1) | IT1115001B (en:Method) |
| LU (1) | LU80861A1 (en:Method) |
| MX (1) | MX5588E (en:Method) |
| NO (1) | NO150483C (en:Method) |
| NZ (1) | NZ189638A (en:Method) |
| PH (1) | PH15171A (en:Method) |
| PL (1) | PL117264B1 (en:Method) |
| PT (1) | PT69220A (en:Method) |
| RO (1) | RO76642A (en:Method) |
| SU (1) | SU810081A3 (en:Method) |
| YU (1) | YU26879A (en:Method) |
| ZA (1) | ZA79513B (en:Method) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2525595A1 (fr) * | 1982-04-27 | 1983-10-28 | Pharmuka Lab | Nouveaux derives d'arene et d'heteroarenecarboxamides et leur utilisation comme medicaments |
| DE3621413A1 (de) * | 1986-06-26 | 1988-01-07 | Boehringer Ingelheim Kg | Verwendung carbocyclisch und heterocyclisch annelierter dihydropyridine als cardioprotektive mittel sowie neue heterocyclisch und carbocyclisch anellierte dihydropyridine, verfahren zu deren herstellung und zwischenstufen fuer deren herstellung |
| WO1988002751A1 (en) * | 1986-10-13 | 1988-04-21 | Asahi Kasei Kogyo Kabushiki Kaisha | Pyridine derivatives |
| JP2010535855A (ja) * | 2007-08-10 | 2010-11-25 | クリスタルゲノミクス、インク． | ピリジン誘導体およびその使用方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3845065A (en) * | 1972-02-18 | 1974-10-29 | Merck & Co Inc | 4-oxo-4,5-dihydrothieno(3,2-c)pyridines |
-
1978
- 1978-02-17 FR FR7804561A patent/FR2417512A1/fr active Granted
-
1979
- 1979-01-26 DE DE7979400053T patent/DE2960109D1/de not_active Expired
- 1979-01-26 EP EP79400053A patent/EP0003920B1/fr not_active Expired
- 1979-01-29 CH CH84479A patent/CH635844A5/fr not_active IP Right Cessation
- 1979-01-30 IE IE163/79A patent/IE47789B1/en not_active IP Right Cessation
- 1979-01-30 GR GR58210A patent/GR66844B/el unknown
- 1979-01-30 IL IL56541A patent/IL56541A/xx unknown
- 1979-01-31 LU LU80861A patent/LU80861A1/xx unknown
- 1979-02-02 ES ES477401A patent/ES477401A1/es not_active Expired
- 1979-02-02 AU AU43897/79A patent/AU519318B2/en not_active Ceased
- 1979-02-06 ZA ZA79513A patent/ZA79513B/xx unknown
- 1979-02-07 YU YU00268/79A patent/YU26879A/xx unknown
- 1979-02-07 AR AR275419A patent/AR227623A1/es active
- 1979-02-07 DK DK50279A patent/DK146046C/da not_active IP Right Cessation
- 1979-02-09 AT AT0098679A patent/AT369369B/de not_active IP Right Cessation
- 1979-02-09 RO RO7996565A patent/RO76642A/ro unknown
- 1979-02-12 FI FI790460A patent/FI66872C/fi not_active IP Right Cessation
- 1979-02-13 NZ NZ189638A patent/NZ189638A/xx unknown
- 1979-02-13 CA CA321,393A patent/CA1126732A/en not_active Expired
- 1979-02-13 PT PT7969220A patent/PT69220A/pt unknown
- 1979-02-14 HU HU79PA1342A patent/HU178075B/hu not_active IP Right Cessation
- 1979-02-15 DD DD79211045A patent/DD142053A5/de not_active IP Right Cessation
- 1979-02-15 IT IT48023/79A patent/IT1115001B/it active
- 1979-02-15 MX MX797720U patent/MX5588E/es unknown
- 1979-02-16 GB GB7905508A patent/GB2014576B/en not_active Expired
- 1979-02-16 PL PL1979213472A patent/PL117264B1/pl unknown
- 1979-02-16 SU SU792728455A patent/SU810081A3/ru active
- 1979-02-16 NO NO790515A patent/NO150483C/no unknown
- 1979-02-16 PH PH22206A patent/PH15171A/en unknown
- 1979-02-16 BE BE0/193507A patent/BE874228A/xx not_active IP Right Cessation
- 1979-02-17 JP JP1778479A patent/JPS54157599A/ja active Granted
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |