CA1038871A - Process for the preparation of new pyridine derivatives - Google Patents
Process for the preparation of new pyridine derivativesInfo
- Publication number
- CA1038871A CA1038871A CA191,469A CA191469A CA1038871A CA 1038871 A CA1038871 A CA 1038871A CA 191469 A CA191469 A CA 191469A CA 1038871 A CA1038871 A CA 1038871A
- Authority
- CA
- Canada
- Prior art keywords
- thieno
- pyridine
- formula
- tetrahydro
- pharmaceutically acceptable
- 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 abstract description 46
- 230000008569 process Effects 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 150000003222 pyridines Chemical class 0.000 title claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical group 0.000 claims abstract description 8
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 229910052717 sulfur Chemical group 0.000 claims abstract description 4
- 239000011593 sulfur Chemical group 0.000 claims abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 101100277337 Arabidopsis thaliana DDM1 gene Proteins 0.000 claims abstract 3
- 101150113676 chr1 gene Proteins 0.000 claims abstract 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- MKYRMMMSZSVIGD-UHFFFAOYSA-N thieno[3,2-c]pyridine Chemical compound N1=CC=C2SC=CC2=C1 MKYRMMMSZSVIGD-UHFFFAOYSA-N 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 4
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 claims description 3
- XXRUQNNAKXZSOS-UHFFFAOYSA-N 5-(chloromethyl)-1,2,3-trimethoxybenzene Chemical compound COC1=CC(CCl)=CC(OC)=C1OC XXRUQNNAKXZSOS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 claims description 3
- MOBRMRJUKNQBMY-UHFFFAOYSA-N 1-(chloromethyl)-2-fluorobenzene Chemical compound FC1=CC=CC=C1CCl MOBRMRJUKNQBMY-UHFFFAOYSA-N 0.000 claims description 2
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 claims description 2
- BASMANVIUSSIIM-UHFFFAOYSA-N 1-chloro-2-(chloromethyl)benzene Chemical compound ClCC1=CC=CC=C1Cl BASMANVIUSSIIM-UHFFFAOYSA-N 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 238000006482 condensation reaction Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 6
- 238000009833 condensation Methods 0.000 claims 5
- 230000005494 condensation Effects 0.000 claims 5
- BOLPTHYAGIONKD-UHFFFAOYSA-N 5-[(2-fluorophenyl)methyl]-6,7-dihydro-4h-thieno[3,2-c]pyridine Chemical compound FC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 BOLPTHYAGIONKD-UHFFFAOYSA-N 0.000 claims 2
- KNSFITOKRGUJFV-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-6,7-dihydro-4h-thieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1CN1CC(C=CS2)=C2CC1 KNSFITOKRGUJFV-UHFFFAOYSA-N 0.000 claims 2
- QDYAYRZVUFLHAK-UHFFFAOYSA-N 5-[(4-methoxyphenyl)methyl]-6,7-dihydro-4h-thieno[3,2-c]pyridine Chemical compound C1=CC(OC)=CC=C1CN1CC(C=CS2)=C2CC1 QDYAYRZVUFLHAK-UHFFFAOYSA-N 0.000 claims 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- WWCDFGZRMWMINX-UHFFFAOYSA-N 5-[(3,4,5-trimethoxyphenyl)methyl]-6,7-dihydro-4h-thieno[3,2-c]pyridine Chemical compound COC1=C(OC)C(OC)=CC(CN2CC=3C=CSC=3CC2)=C1 WWCDFGZRMWMINX-UHFFFAOYSA-N 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
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- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 16
- 238000012360 testing method Methods 0.000 description 15
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
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- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 4
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- WJDMEHCIRPKRRQ-UHFFFAOYSA-N furo[3,2-c]pyridine Chemical class N1=CC=C2OC=CC2=C1 WJDMEHCIRPKRRQ-UHFFFAOYSA-N 0.000 description 2
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- 229960001317 isoprenaline Drugs 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 210000001872 metatarsal bone Anatomy 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 1
- 229960003343 ouabain Drugs 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical group O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
- 230000000793 phophlogistic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000820 toxicity test 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
- 230000002792 vascular Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 206010047302 ventricular tachycardia Diseases 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- 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]
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7303503A FR2215948B1 (en, 2012) | 1973-02-01 | 1973-02-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1038871A true CA1038871A (en) | 1978-09-19 |
Family
ID=9114160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA191,469A Expired CA1038871A (en) | 1973-02-01 | 1974-01-31 | Process for the preparation of new pyridine derivatives |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4051141A (en, 2012) |
| JP (1) | JPS5231357B2 (en, 2012) |
| AT (1) | AT338261B (en, 2012) |
| AU (1) | AU473141B2 (en, 2012) |
| BE (1) | BE809812A (en, 2012) |
| CA (1) | CA1038871A (en, 2012) |
| CH (1) | CH593287A5 (en, 2012) |
| DK (1) | DK136651B (en, 2012) |
| ES (2) | ES422581A1 (en, 2012) |
| FR (1) | FR2215948B1 (en, 2012) |
| GB (1) | GB1445524A (en, 2012) |
| IL (3) | IL44061A (en, 2012) |
| NL (1) | NL7401237A (en, 2012) |
| PH (2) | PH11451A (en, 2012) |
| SE (2) | SE416203B (en, 2012) |
| ZA (1) | ZA74488B (en, 2012) |
Families Citing this family (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2345150A2 (fr) * | 1975-08-06 | 1977-10-21 | Centre Etd Ind Pharma | Nouveaux derives de la thienopyridine, et leur application |
| FR2313055A2 (fr) * | 1975-06-05 | 1976-12-31 | Parcor | Nouveaux derives substitues de la thieno-pyridine, leur procede de preparation et leurs applications |
| FR2312246A1 (fr) * | 1975-05-28 | 1976-12-24 | Parcor | Derives de la tetrahydro-4,5,6,7 thieno (3,2-c) pyridine, leur procede de preparation et leurs applications |
| FR2312247A1 (fr) * | 1975-05-30 | 1976-12-24 | Parcor | Derives de la thieno-pyridine, leur procede de preparation et leurs applications |
| FR2315274A1 (fr) * | 1975-06-27 | 1977-01-21 | Parcor | Nouveaux derives de la thieno (2,3-c) pyridine, leur preparation et leurs applications |
| US4163852A (en) * | 1975-07-09 | 1979-08-07 | Parcor | Process for the preparation of tetrahydro-thieno[3,2-c]- and [2,3-c]pyridine derivatives |
| ZA767652B (en) * | 1976-01-02 | 1977-11-30 | Centre Etd Ind Pharma | Process for the treatment of patients suffering from disorders induced by sludging |
| FR2338703A1 (fr) * | 1976-01-22 | 1977-08-19 | Parcor | Derives de thieno (3,2-c) pyridine, leur procede de preparation et leurs applications |
| FR2376860A1 (fr) * | 1977-01-07 | 1978-08-04 | Parcor | Tetrahydro-4,5,6,7 thieno (2,3-c) et (3,2-c) pyridines, leur procede de preparation et leur application therapeutique |
| GB2038178B (en) * | 1978-12-29 | 1983-03-09 | Parcor | Antithrombotic therapeutic compsition |
| US4464377A (en) * | 1977-06-22 | 1984-08-07 | BLANCHARD Jean | Anti-thrombotic therapeutic compositions |
| FR2395028A2 (fr) * | 1977-06-22 | 1979-01-19 | Centre Etd Ind Pharma | Derives pyridiniques, leur preparation et leurs application therapeutique |
| GB2038625B (en) * | 1978-12-29 | 1983-01-12 | Parcor | Therapeutic composition having an antithrombotic and antiblood-platelet-aggregating activity |
| FR2397417A1 (fr) * | 1977-07-12 | 1979-02-09 | Parcor | Procede de preparation de derives de la thienopyridine |
| JPS5498337A (en) * | 1978-01-06 | 1979-08-03 | Dai Ichi Seiyaku Co Ltd | Anticarcinogenic and/or antimetastatic agent |
| JPS54105236A (en) * | 1978-02-06 | 1979-08-18 | Dai Ichi Seiyaku Co Ltd | Antithrombogenetic agent for shunt and/or artificial blood vessel |
| FR2426046A1 (fr) | 1978-05-18 | 1979-12-14 | Synthelabo | Derive de tetrahydro-isoquinoleine, sa preparation et son application en therapeutique |
| US4490377A (en) * | 1980-07-29 | 1984-12-25 | Syntex (U.S.A.) Inc. | Acid stabilized compositions of thieno-pyridine derived compounds |
| US4321266A (en) * | 1980-10-06 | 1982-03-23 | Sanofi | 5-o-Cyanobenzyl-4,5,6,7-tetrahydrothieno [3,2-C] pyridine |
| US4400384A (en) * | 1980-10-06 | 1983-08-23 | Sanofi, S.A. | 5-o-Cyanobenzyl-4,5,6,7-tetrahydrothieno [3,2-c] pyridine methanesulfonate and other novel salts thereof |
| FR2495158A1 (fr) * | 1980-11-28 | 1982-06-04 | Sanofi Sa | Nouveau procede de preparation de derives de la tetrahydro-5, 6, 7, 7a 4h-thieno (3, 2-c) pyridinone-2 |
| 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 |
| FR2495156A1 (fr) * | 1980-11-28 | 1982-06-04 | Sanofi Sa | Derives de la thieno-pyridinone, leur procede de preparation et leur application therapeutique |
| FR2508442A1 (fr) * | 1981-06-30 | 1982-12-31 | Sanofi Sa | Procede de preparation d'ethylamines b-cyclo-substituees et produits ainsi obtenus |
| FR2530247B1 (fr) * | 1982-07-13 | 1986-05-16 | Sanofi Sa | Nouveaux derives de la thieno (3, 2-c) pyridine, leur procede de preparation et leur application therapeutique |
| IT8222600A0 (it) * | 1982-07-28 | 1982-07-28 | Pietro Tommaso Tessitore | Nuovi idrossibenzensolfonati della 5-(o-clorobenzil)-4,5,6,7-tetraidro tieno parentesi quadra aperta 3,2-c parentesi quadra chiusa piridina. |
| JPS6044344U (ja) * | 1983-09-03 | 1985-03-28 | オムロン株式会社 | リレ−の駆動回路 |
| FR2566775B1 (fr) * | 1984-06-27 | 1986-10-31 | Synthelabo | Derives de tetrahydro-4,5,6,7 furo ou 1h-pyrrolo(2,3-c)pyridine, leur preparation et leur application en therapeutique |
| FR2570701B1 (fr) * | 1984-09-27 | 1987-05-22 | Synthelabo | Derives de furo(3,2-c)pyridines, leur preparation et leur application en therapeutique |
| JPS6185391A (ja) * | 1984-10-03 | 1986-04-30 | Nisshin Flour Milling Co Ltd | ５−（２−クロロベンジル）−４，５，６，７−テトラヒドロチエノ〔３，２−ｃ〕ピリジンの製造方法 |
| GB8429087D0 (en) * | 1984-11-16 | 1984-12-27 | Scras | Thienopyridine derivatives |
| FR2612777A1 (fr) * | 1987-03-26 | 1988-09-30 | Inst Nat Sante Rech Med | Composition medicamenteuse pour le traitement et la prevention de maladies dues a une cytotoxicite a mediation cellulaire, renfermant au moins un derive de la pyridine comme principe actif |
| US4906756A (en) * | 1988-05-10 | 1990-03-06 | Syntex (U.S.A.) Inc. | 2-(2-nitrovinyl)thiophene reduction and synthesis of thieno[3,2-c]pyridine derivatives |
| US4879313A (en) * | 1988-07-20 | 1989-11-07 | Mosanto Company | Novel platelet-aggregation inhibitors |
| US5053393A (en) * | 1988-07-20 | 1991-10-01 | Monsanto Company | Novel platelet-aggregation inhibitor |
| US4992463A (en) * | 1988-07-20 | 1991-02-12 | Monsanto Company | Thienyl peptide mimetic compounds which are useful in inhibiting platelet aggregation |
| US5037808A (en) * | 1988-07-20 | 1991-08-06 | Monsanto Co. | Indolyl platelet-aggregation inhibitors |
| JPH02145581A (ja) * | 1988-10-11 | 1990-06-05 | Lonza Ag | 置換チエニルエチルアミンとその製造方法 |
| GB8824400D0 (en) * | 1988-10-18 | 1988-11-23 | Glaxo Group Ltd | Chemical compounds |
| US4997945A (en) * | 1990-01-25 | 1991-03-05 | Syntex (U.S.A.) Inc. | Carbamate salts of 2-(2'-thienyl)alkylamines |
| FI101150B (fi) * | 1991-09-09 | 1998-04-30 | Sankyo Co | Menetelmä lääkeaineina käyttökelpoisten tetrahydrotienopyridiinin johd annaisten valmistamiseksi |
| CA2087743C (en) * | 1992-02-06 | 1999-04-27 | Akio Odawara | Pharmaceutical composition for inhibiting platelet aggregation |
| US5296603A (en) * | 1992-06-08 | 1994-03-22 | Fuji Photo Film Co., Ltd. | 3-amino-5-o-chlorobenzyl-4,5,6,7-tetrahydrothieno[3,2-c]-pyridine-2-carboxylic acid compounds |
| US5294621A (en) * | 1992-10-07 | 1994-03-15 | Ortho Pharmaceutical Corporation | Thieno tetrahydropyridines useful as class III antiarrhythmic agents |
| NZ334389A (en) * | 1996-08-28 | 2001-05-25 | Ube Industries | Cyclic amine derivatives |
| US6043368A (en) * | 1996-09-04 | 2000-03-28 | Poli Industria Chimica, S.P.A. | Method of making thieno-pyridine derivatives |
| US5872128A (en) * | 1997-10-15 | 1999-02-16 | Invamed, Inc. | Stabilized composition of ticlopidine hydrochloride |
| DE69907166T2 (de) | 1998-02-27 | 2004-02-05 | Sankyo Co., Ltd. | Zyklische aminoverbindungen |
| US20090297597A1 (en) * | 1998-11-02 | 2009-12-03 | Gary Liversidge | Modified Release Ticlopidine Compositions |
| US20080113025A1 (en) * | 1998-11-02 | 2008-05-15 | Elan Pharma International Limited | Compositions comprising nanoparticulate naproxen and controlled release hydrocodone |
| WO2007011473A1 (en) * | 2005-06-12 | 2007-01-25 | Elan Corporation, Plc | Modified release ticlopidine compositions |
| JP4694669B2 (ja) | 1999-03-17 | 2011-06-08 | 第一三共株式会社 | 医薬組成物 |
| ES2311498T3 (es) | 2000-12-25 | 2009-02-16 | Daiichi Sankyo Company, Limited | Composiciones medicinales que contienen aspirina. |
| US6495691B1 (en) | 2001-07-06 | 2002-12-17 | Brantford Chemicals Inc. | Process for the preparation of tetrahydrothieno[3,2-c]pyridine derivatives |
| US20050192245A1 (en) * | 2002-07-18 | 2005-09-01 | Sankyo Company, Limited | Medicinal composition for treating arteriosclerosis |
| CA2454015C (en) * | 2003-12-23 | 2009-11-24 | Brantford Chemicals Inc. | A process for the preparation of tetrahydrothieno [3,2-c] pyridine derivatives |
| US20100062066A1 (en) * | 2006-11-14 | 2010-03-11 | Acusphere, Inc | Formulations of Tetrahydropyridine Antiplatelet Agents for Parenteral or Oral Administration |
| EP1980563A1 (en) | 2007-04-09 | 2008-10-15 | BATTULA, Srinivasa Reddy | Procedure for the preparation of methyl (+)-(S)-Alpha-(O-chlorophenyl)-6,7-dihydrothieno-[3,2-C]pyridine-5(4H) acetate |
| WO2008156858A2 (en) * | 2007-06-20 | 2008-12-24 | University Of Utah Research Foundation | Use of pre-mrna splicing in platelet cells for the diagnosis of disease |
| 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 |
| DE102014108210A1 (de) | 2014-06-11 | 2015-12-17 | Dietrich Gulba | Rodentizid |
| EP4070658A1 (de) | 2021-04-06 | 2022-10-12 | BIORoxx GmbH | Verwendung von blutgerinnungshemmenden verbindungen als rodentizide |
-
1973
- 1973-02-01 FR FR7303503A patent/FR2215948B1/fr not_active Expired
-
1974
- 1974-01-15 CH CH49874A patent/CH593287A5/xx not_active IP Right Cessation
- 1974-01-16 BE BE139867A patent/BE809812A/xx not_active IP Right Cessation
- 1974-01-22 IL IL44061A patent/IL44061A/en unknown
- 1974-01-22 IL IL49786A patent/IL49786A/en unknown
- 1974-01-23 ZA ZA740488A patent/ZA74488B/xx unknown
- 1974-01-24 ES ES422581A patent/ES422581A1/es not_active Expired
- 1974-01-28 SE SE7401036A patent/SE416203B/xx active Protection Beyond IP Right Term
- 1974-01-28 AT AT67874A patent/AT338261B/de not_active IP Right Cessation
- 1974-01-29 NL NL7401237A patent/NL7401237A/xx unknown
- 1974-01-29 PH PH15449A patent/PH11451A/en unknown
- 1974-01-30 AU AU65010/74A patent/AU473141B2/en not_active Expired
- 1974-01-30 GB GB439274A patent/GB1445524A/en not_active Expired
- 1974-01-31 JP JP49013559A patent/JPS5231357B2/ja not_active Expired
- 1974-01-31 CA CA191,469A patent/CA1038871A/en not_active Expired
- 1974-02-01 DK DK55574AA patent/DK136651B/da not_active IP Right Cessation
-
1976
- 1976-02-20 US US05/660,248 patent/US4051141A/en not_active Expired - Lifetime
- 1976-03-02 ES ES445702A patent/ES445702A1/es not_active Expired
- 1976-04-30 PH PH18386A patent/PH11759A/en unknown
- 1976-06-14 IL IL49786A patent/IL49786A0/xx unknown
-
1977
- 1977-03-17 SE SE7703028A patent/SE421624B/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU6501074A (en) | 1975-07-31 |
| IL49786A (en) | 1977-06-30 |
| SE416203B (sv) | 1980-12-08 |
| ATA67874A (de) | 1976-12-15 |
| SE7703028L (sv) | 1977-03-17 |
| DE2404308A1 (de) | 1974-08-08 |
| IL44061A (en) | 1977-06-30 |
| AU473141B2 (en) | 1976-06-17 |
| GB1445524A (en) | 1976-08-11 |
| ES445702A1 (es) | 1977-06-01 |
| FR2215948A1 (en, 2012) | 1974-08-30 |
| ZA74488B (en) | 1974-11-27 |
| ES422581A1 (es) | 1976-10-01 |
| DK136651C (en, 2012) | 1978-04-17 |
| CH593287A5 (en, 2012) | 1977-11-30 |
| PH11759A (en) | 1978-06-27 |
| IL49786A0 (en) | 1976-08-31 |
| BE809812A (fr) | 1974-07-16 |
| JPS5046688A (en, 2012) | 1975-04-25 |
| AT338261B (de) | 1977-08-10 |
| JPS5231357B2 (en, 2012) | 1977-08-13 |
| PH11451A (en) | 1978-02-01 |
| US4051141A (en) | 1977-09-27 |
| DK136651B (da) | 1977-11-07 |
| DE2404308B2 (de) | 1977-06-30 |
| FR2215948B1 (en, 2012) | 1976-05-14 |
| NL7401237A (en, 2012) | 1974-08-05 |
| SE421624B (sv) | 1982-01-18 |
| IL44061A0 (en) | 1974-05-16 |
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