NO780050L - Fremgangsmaate ved fremstilling av 4,5,6,7-tetrahydrothieno-(2,3-c) og (3,2-c)pyridiner - Google Patents
Fremgangsmaate ved fremstilling av 4,5,6,7-tetrahydrothieno-(2,3-c) og (3,2-c)pyridinerInfo
- Publication number
- NO780050L NO780050L NO780050A NO780050A NO780050L NO 780050 L NO780050 L NO 780050L NO 780050 A NO780050 A NO 780050A NO 780050 A NO780050 A NO 780050A NO 780050 L NO780050 L NO 780050L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- derivative
- pyridine
- tetrahydro
- thieno
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 42
- 238000002360 preparation method Methods 0.000 title claims description 3
- RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical compound NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
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- -1 calcium carbonate Chemical class 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 8
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- 241001465754 Metazoa Species 0.000 description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
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- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
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- UXRSSURLNXLHQP-UHFFFAOYSA-N 4-hydroxy-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-5-carboxylic acid Chemical compound OC1C(C(O)=O)NCC2=C1C=CS2 UXRSSURLNXLHQP-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 208000007536 Thrombosis Diseases 0.000 description 4
- 238000009825 accumulation Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000002504 physiological saline solution Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- DKASUYIOUPPQSY-UHFFFAOYSA-N 2,3,3a,4-tetrahydrothieno[2,3-c]pyridine Chemical compound C1C=NC=C2SCCC21 DKASUYIOUPPQSY-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 102000007327 Protamines Human genes 0.000 description 3
- 108010007568 Protamines Proteins 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 241000700157 Rattus norvegicus Species 0.000 description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
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- 210000004027 cell Anatomy 0.000 description 3
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- OMGBSCDDGFBXFH-UHFFFAOYSA-N 2-chloro-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-6-carboxylic acid Chemical compound C1NC(C(=O)O)CC2=C1C=C(Cl)S2 OMGBSCDDGFBXFH-UHFFFAOYSA-N 0.000 description 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- BPJIVYMZHDBREO-UHFFFAOYSA-N 5-methyl-6,7-dihydro-4h-thieno[3,2-c]pyridine-6-carboxylic acid Chemical compound C1C(C(O)=O)N(C)CC2=C1SC=C2 BPJIVYMZHDBREO-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
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- 239000003146 anticoagulant agent Substances 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- MIIQPKNTDAVETD-UHFFFAOYSA-N benzyl 5-benzyl-2-chloro-6,7-dihydro-4h-thieno[3,2-c]pyridine-6-carboxylate Chemical compound C=1C=CC=CC=1COC(=O)C1CC=2SC(Cl)=CC=2CN1CC1=CC=CC=C1 MIIQPKNTDAVETD-UHFFFAOYSA-N 0.000 description 1
- YMVMLOLCHUVAJB-UHFFFAOYSA-N benzyl 5-benzyl-6,7-dihydro-4h-thieno[3,2-c]pyridine-6-carboxylate Chemical compound C1C=2SC=CC=2CN(CC=2C=CC=CC=2)C1C(=O)OCC1=CC=CC=C1 YMVMLOLCHUVAJB-UHFFFAOYSA-N 0.000 description 1
- OITBJHJUNGHDCD-UHFFFAOYSA-N benzyl 5-benzyl-7-hydroxy-6,7-dihydro-4h-thieno[3,2-c]pyridine-6-carboxylate Chemical compound C1C=2C=CSC=2C(O)C(C(=O)OCC=2C=CC=CC=2)N1CC1=CC=CC=C1 OITBJHJUNGHDCD-UHFFFAOYSA-N 0.000 description 1
- OHPQDKOQSJDVGI-UHFFFAOYSA-N benzyl 6-benzyl-4-hydroxy-5,7-dihydro-4h-thieno[2,3-c]pyridine-5-carboxylate Chemical compound C1C=2SC=CC=2C(O)C(C(=O)OCC=2C=CC=CC=2)N1CC1=CC=CC=C1 OHPQDKOQSJDVGI-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- OOEDCKPBQBXVKG-UHFFFAOYSA-N butyl 5-butyl-6,7-dihydro-4h-thieno[3,2-c]pyridine-6-carboxylate Chemical compound C1N(CCCC)C(C(=O)OCCCC)CC2=C1C=CS2 OOEDCKPBQBXVKG-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000009109 curative therapy Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- OYJXTOVLKZDGFK-UHFFFAOYSA-N ethanol;2-propan-2-yloxypropane Chemical compound CCO.CC(C)OC(C)C OYJXTOVLKZDGFK-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- UUWYVTCARWQSOL-UHFFFAOYSA-N ethyl 5-benzyl-2-chloro-6,7-dihydro-4h-thieno[3,2-c]pyridine-6-carboxylate Chemical compound CCOC(=O)C1CC=2SC(Cl)=CC=2CN1CC1=CC=CC=C1 UUWYVTCARWQSOL-UHFFFAOYSA-N 0.000 description 1
- NDOKRSSIKZONHR-UHFFFAOYSA-N ethyl 5-methyl-6,7-dihydro-4h-thieno[3,2-c]pyridine-6-carboxylate Chemical compound C1N(C)C(C(=O)OCC)CC2=C1C=CS2 NDOKRSSIKZONHR-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010562 histological examination Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- 239000011630 iodine Chemical group 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
- 239000011976 maleic acid Substances 0.000 description 1
- BVUDBDGNIWFUHT-UHFFFAOYSA-N methyl 2-chloro-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-6-carboxylate;hydrochloride Chemical compound Cl.C1NC(C(=O)OC)CC2=C1C=C(Cl)S2 BVUDBDGNIWFUHT-UHFFFAOYSA-N 0.000 description 1
- RFQCFNOOWUTVOE-UHFFFAOYSA-N methyl 2-chloro-5-[(2-chlorophenyl)methyl]-6,7-dihydro-4H-thieno[3,2-c]pyridine-6-carboxylate Chemical compound ClC1=CC=2CN(C(CC=2S1)C(=O)OC)CC1=C(C=CC=C1)Cl RFQCFNOOWUTVOE-UHFFFAOYSA-N 0.000 description 1
- FTGDKCWSJJIFNP-UHFFFAOYSA-N methyl 2-chloro-6,7-dihydro-4h-thieno[3,2-c]pyridine-5-carboxylate Chemical compound C1N(C(=O)OC)CCC2=C1C=C(Cl)S2 FTGDKCWSJJIFNP-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000006504 o-cyanobenzyl group Chemical group [H]C1=C([H])C(C#N)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000001936 parietal effect Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229940125670 thienopyridine Drugs 0.000 description 1
- 239000002175 thienopyridine Substances 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 238000002627 tracheal intubation Methods 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
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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 |
|---|---|---|---|
| FR7700408A FR2376860A1 (fr) | 1977-01-07 | 1977-01-07 | Tetrahydro-4,5,6,7 thieno (2,3-c) et (3,2-c) pyridines, leur procede de preparation et leur application therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO780050L true NO780050L (no) | 1978-07-10 |
Family
ID=9185247
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO780050A NO780050L (no) | 1977-01-07 | 1978-01-06 | Fremgangsmaate ved fremstilling av 4,5,6,7-tetrahydrothieno-(2,3-c) og (3,2-c)pyridiner |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US4147787A (el) |
| JP (1) | JPS6040436B2 (el) |
| AR (1) | AR217668A1 (el) |
| AT (1) | AT357532B (el) |
| AU (1) | AU508277B2 (el) |
| BE (1) | BE862695A (el) |
| CA (1) | CA1087187A (el) |
| CH (1) | CH631179A5 (el) |
| DD (1) | DD133673A5 (el) |
| DE (1) | DE2800596C2 (el) |
| DK (1) | DK147826C (el) |
| ES (1) | ES465683A1 (el) |
| FI (1) | FI62308C (el) |
| FR (1) | FR2376860A1 (el) |
| GB (1) | GB1574394A (el) |
| GR (1) | GR66061B (el) |
| HU (1) | HU175645B (el) |
| IE (1) | IE46288B1 (el) |
| IL (1) | IL53708A (el) |
| LU (1) | LU78816A1 (el) |
| MX (1) | MX5274E (el) |
| NL (1) | NL184220C (el) |
| NO (1) | NO780050L (el) |
| NZ (1) | NZ186168A (el) |
| PH (1) | PH12856A (el) |
| PL (1) | PL118048B1 (el) |
| PT (1) | PT67501B (el) |
| SE (1) | SE421922B (el) |
| SU (1) | SU683625A3 (el) |
| YU (1) | YU40023B (el) |
| ZA (1) | ZA7833B (el) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE816390A (en) * | 1973-06-15 | 1974-12-16 | Vinyl or ethynyl-substd. mercapto-methyl pyridines - for treatment of rheumatoid arthritis and inflammatory troubles | |
| 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 |
| US4448779A (en) * | 1981-07-16 | 1984-05-15 | Sanofi | Use of MS salt in geriatric medicine |
| US4775757A (en) * | 1986-09-22 | 1988-10-04 | Ortho Pharmaceutical Corporation | Thienopyridines useful as cardiovascular agents |
| 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 |
| US5342953A (en) * | 1991-01-31 | 1994-08-30 | Syntex (U.S.A.) Inc. | N-2-chlorobenzyl-2-oxo and N-2-chlorobenzyl-2,2-dioxo-1,2,3-oxathiazolidine derivatives, their preparation and synthesis of thieno[3,2-c]pyridine derivatives therefrom |
| ES2130192T3 (es) * | 1992-07-31 | 1999-07-01 | Hoechst Ag | Procedimiento para la preparacion biotecnica de l-tienilalaninas en forma enantiomera pura, partiendo de acidos 2-hidroxi-3-tienil-acrilicos, y su empleo. |
| FR2710495B1 (fr) * | 1993-09-28 | 1995-10-27 | Celaflor Gmbh | Dispositif pour effectuer des traitements insecticides, et leur utilisation dans les habitations. |
| IL113196A0 (en) | 1994-03-31 | 1995-06-29 | Bristol Myers Squibb Co | Imidazole derivatives and pharmaceutical compositions containing the same |
| AU4288599A (en) * | 1998-07-01 | 2000-01-24 | Sun Pharmaceutical Industries Ltd. | Stable pharmaceutical compositions of thieno (3,2-c) pyridine derivatives |
| US6323215B1 (en) | 1999-07-09 | 2001-11-27 | Ortho-Mcneil Pharmaceutical, Inc. | Neurotrophic tetrahydroisoquinolines and tetrahydrothienopyridines, and related compositions and methods |
| HUP0400644A3 (en) * | 2000-12-25 | 2009-06-29 | Ube Industries | Pharmaceutical compositions containing aspirin |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3823151A (en) * | 1968-08-02 | 1974-07-09 | Ciba Geigy Corp | 4,5,6,7-tetrahydrothieno(2,3-d)pyridines |
| FR2215948B1 (el) * | 1973-02-01 | 1976-05-14 | Centre Etd Ind Pharma | |
| US3997545A (en) * | 1973-07-23 | 1976-12-14 | Takeda Chemical Industries, Ltd. | Thienopyridine-carboxylic acid derivatives |
| 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 |
-
1977
- 1977-01-07 FR FR7700408A patent/FR2376860A1/fr active Granted
- 1977-12-22 YU YU3040/77A patent/YU40023B/xx unknown
- 1977-12-27 US US05/864,939 patent/US4147787A/en not_active Expired - Lifetime
- 1977-12-28 IL IL53708A patent/IL53708A/xx unknown
- 1977-12-30 SE SE7714940A patent/SE421922B/sv not_active IP Right Cessation
- 1977-12-30 IE IE2655/77A patent/IE46288B1/en unknown
-
1978
- 1978-01-02 NL NLAANVRAGE7800034,A patent/NL184220C/xx not_active IP Right Cessation
- 1978-01-03 HU HU78PA1299A patent/HU175645B/hu unknown
- 1978-01-03 GB GB68/78A patent/GB1574394A/en not_active Expired
- 1978-01-04 AT AT6178A patent/AT357532B/de not_active IP Right Cessation
- 1978-01-04 CA CA294,348A patent/CA1087187A/en not_active Expired
- 1978-01-04 CH CH7178A patent/CH631179A5/fr not_active IP Right Cessation
- 1978-01-04 ZA ZA00780033A patent/ZA7833B/xx unknown
- 1978-01-04 GR GR55094A patent/GR66061B/el unknown
- 1978-01-05 ES ES465683A patent/ES465683A1/es not_active Expired
- 1978-01-05 DD DD7800203109A patent/DD133673A5/xx not_active IP Right Cessation
- 1978-01-05 LU LU78816A patent/LU78816A1/xx unknown
- 1978-01-05 AR AR270641A patent/AR217668A1/es active
- 1978-01-06 PT PT67501A patent/PT67501B/pt unknown
- 1978-01-06 AU AU32238/78A patent/AU508277B2/en not_active Expired
- 1978-01-06 SU SU782562904A patent/SU683625A3/ru active
- 1978-01-06 FI FI780048A patent/FI62308C/fi not_active IP Right Cessation
- 1978-01-06 NO NO780050A patent/NO780050L/no unknown
- 1978-01-06 MX MX786754U patent/MX5274E/es unknown
- 1978-01-06 NZ NZ186168A patent/NZ186168A/xx unknown
- 1978-01-06 DK DK7578A patent/DK147826C/da not_active IP Right Cessation
- 1978-01-06 PL PL1978203863A patent/PL118048B1/pl unknown
- 1978-01-06 BE BE184146A patent/BE862695A/xx not_active IP Right Cessation
- 1978-01-07 DE DE2800596A patent/DE2800596C2/de not_active Expired
- 1978-01-07 JP JP53000787A patent/JPS6040436B2/ja not_active Expired
- 1978-01-09 PH PH20633A patent/PH12856A/en unknown
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