FI63942C - Foerfarande foer framstaellning av farmakologiskt vaerdefulla 4-fenyl-tieno-(2,3-c)-piperidiner och deras syraadditionssalter - Google Patents
Foerfarande foer framstaellning av farmakologiskt vaerdefulla 4-fenyl-tieno-(2,3-c)-piperidiner och deras syraadditionssalter Download PDFInfo
- Publication number
- FI63942C FI63942C FI783125A FI783125A FI63942C FI 63942 C FI63942 C FI 63942C FI 783125 A FI783125 A FI 783125A FI 783125 A FI783125 A FI 783125A FI 63942 C FI63942 C FI 63942C
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- FI
- Finland
- Prior art keywords
- alkyl group
- formula
- carbon atoms
- compound
- chlorine
- Prior art date
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- XURYGPTVBIUZEP-UHFFFAOYSA-N 4-phenyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine Chemical compound C1NCC=2SC=CC=2C1C1=CC=CC=C1 XURYGPTVBIUZEP-UHFFFAOYSA-N 0.000 title 1
- 230000000144 pharmacologic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 37
- 239000000460 chlorine Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- 230000031709 bromination Effects 0.000 claims description 4
- 238000005893 bromination reaction Methods 0.000 claims description 4
- 238000005660 chlorination reaction Methods 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 238000002474 experimental method Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
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- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
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- FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
- 230000001519 thymoleptic effect Effects 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 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
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772746443 DE2746443C2 (de) | 1977-10-15 | 1977-10-15 | 4-Phenyl-thieno-[2,3-c]-piperidine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen |
| DE2746443 | 1977-10-15 | ||
| DE19782833378 DE2833378A1 (de) | 1978-07-29 | 1978-07-29 | Neue 4-phenyl-thieno-eckige klammer auf 2,3-c eckige klammer zu -piperidine, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zusammensetzungen |
| DE2833378 | 1978-07-29 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI783125A7 FI783125A7 (fi) | 1979-04-16 |
| FI63942B FI63942B (fi) | 1983-05-31 |
| FI63942C true FI63942C (fi) | 1983-09-12 |
Family
ID=25772905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI783125A FI63942C (fi) | 1977-10-15 | 1978-10-13 | Foerfarande foer framstaellning av farmakologiskt vaerdefulla 4-fenyl-tieno-(2,3-c)-piperidiner och deras syraadditionssalter |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US4322423A (cs) |
| JP (1) | JPS5470296A (cs) |
| AT (1) | AT368504B (cs) |
| AU (1) | AU522759B2 (cs) |
| BG (1) | BG28715A3 (cs) |
| CA (1) | CA1113095A (cs) |
| CH (1) | CH644126A5 (cs) |
| CS (1) | CS204036B2 (cs) |
| DD (1) | DD139581A5 (cs) |
| DK (1) | DK150158C (cs) |
| ES (1) | ES474218A1 (cs) |
| FI (1) | FI63942C (cs) |
| FR (1) | FR2405948A1 (cs) |
| GB (1) | GB2007219B (cs) |
| GR (1) | GR65251B (cs) |
| HU (1) | HU176486B (cs) |
| IE (1) | IE47455B1 (cs) |
| IL (1) | IL55727A (cs) |
| IT (1) | IT1109215B (cs) |
| LU (1) | LU80366A1 (cs) |
| NL (1) | NL7810307A (cs) |
| NO (1) | NO151324C (cs) |
| NZ (1) | NZ188645A (cs) |
| PL (1) | PL126597B1 (cs) |
| PT (1) | PT68656A (cs) |
| RO (1) | RO75532A (cs) |
| SE (1) | SE442510B (cs) |
| SU (1) | SU718011A3 (cs) |
| YU (1) | YU240178A (cs) |
| ZA (1) | ZA785769B (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2927294A1 (de) * | 1979-07-06 | 1981-01-08 | Boehringer Sohn Ingelheim | Neue 4-phenyl-4,5,6,7-tetrahydropyrrolo eckige klammer auf 2,3-c eckige klammer zu pyridine, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen |
| US4282227A (en) * | 1980-05-22 | 1981-08-04 | Smithkline Corporation | Renal vasodilating 3,4-dihydroxyphenyltetrahydrothienopyridines |
| DD210278A5 (de) * | 1982-03-05 | 1984-06-06 | Boehringer Ingelheim Kg | Verfahren zur herstellung neuer basisch substituierter 4-phenyl-4,5,6,7-tetrahydro-thieno-(2,3-c)pyridine |
| IL71661A0 (en) * | 1983-04-27 | 1984-07-31 | Boehringer Ingelheim Kg | 4-phenyl-tetrahydro-furano-pyridines,their preparation and pharmaceutical compositions containing them |
| US4572911A (en) * | 1984-08-02 | 1986-02-25 | Mcneilab, Inc. | Hexahydroindolinzine compounds, pharmaceutical compositions and methods and intermediates |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3651068A (en) * | 1969-11-13 | 1972-03-21 | Colgate Palmolive Co | Derivatives of 1 2 3 4-tetrahydrobenzothieno(2 3-c)pyridines |
| FR2315274A1 (fr) * | 1975-06-27 | 1977-01-21 | Parcor | Nouveaux derives de la thieno (2,3-c) pyridine, leur preparation et leurs applications |
| FR2358150A1 (fr) * | 1976-07-13 | 1978-02-10 | Parcor | Nouvelles thieno (2,3-c) et (3,2-c) pyridines, leur procede de preparation et leur application |
| GB1576511A (en) * | 1977-03-29 | 1980-10-08 | Parcor | Thieno(2,3 - c) and (3,2 - c) pyridines process for their preparation and therapeutic applications thereof |
-
1978
- 1978-10-03 AT AT0710978A patent/AT368504B/de not_active IP Right Cessation
- 1978-10-05 GR GR57383A patent/GR65251B/el unknown
- 1978-10-10 SU SU782673554A patent/SU718011A3/ru active
- 1978-10-10 RO RO7895375A patent/RO75532A/ro unknown
- 1978-10-11 CH CH1056578A patent/CH644126A5/de not_active IP Right Cessation
- 1978-10-12 DD DD78208420A patent/DD139581A5/de unknown
- 1978-10-12 YU YU02401/78A patent/YU240178A/xx unknown
- 1978-10-13 NO NO783481A patent/NO151324C/no unknown
- 1978-10-13 NZ NZ188645A patent/NZ188645A/xx unknown
- 1978-10-13 GB GB7840431A patent/GB2007219B/en not_active Expired
- 1978-10-13 NL NL7810307A patent/NL7810307A/xx not_active Application Discontinuation
- 1978-10-13 DK DK458078A patent/DK150158C/da not_active IP Right Cessation
- 1978-10-13 AU AU40698/78A patent/AU522759B2/en not_active Expired
- 1978-10-13 IE IE2050/78A patent/IE47455B1/en unknown
- 1978-10-13 CS CS786668A patent/CS204036B2/cs unknown
- 1978-10-13 SE SE7810728A patent/SE442510B/sv not_active IP Right Cessation
- 1978-10-13 ZA ZA785769A patent/ZA785769B/xx unknown
- 1978-10-13 HU HU78BO1740A patent/HU176486B/hu unknown
- 1978-10-13 LU LU80366A patent/LU80366A1/de unknown
- 1978-10-13 IL IL55727A patent/IL55727A/xx unknown
- 1978-10-13 FR FR7829335A patent/FR2405948A1/fr active Granted
- 1978-10-13 PT PT68656A patent/PT68656A/pt unknown
- 1978-10-13 JP JP12605578A patent/JPS5470296A/ja active Pending
- 1978-10-13 BG BG041084A patent/BG28715A3/xx unknown
- 1978-10-13 IT IT51501/78A patent/IT1109215B/it active
- 1978-10-13 CA CA313,339A patent/CA1113095A/en not_active Expired
- 1978-10-13 FI FI783125A patent/FI63942C/fi not_active IP Right Cessation
- 1978-10-13 PL PL1978210271A patent/PL126597B1/pl unknown
- 1978-10-14 ES ES474218A patent/ES474218A1/es not_active Expired
-
1980
- 1980-03-27 US US06/134,441 patent/US4322423A/en not_active Expired - Lifetime
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: C.H. BOEHRINGER SOHN |