GB1465581A - Tetrahydropyridine and piperidine derivatives and processes for the preparation thereof - Google Patents
Tetrahydropyridine and piperidine derivatives and processes for the preparation thereofInfo
- Publication number
- GB1465581A GB1465581A GB927974A GB927974A GB1465581A GB 1465581 A GB1465581 A GB 1465581A GB 927974 A GB927974 A GB 927974A GB 927974 A GB927974 A GB 927974A GB 1465581 A GB1465581 A GB 1465581A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- alkyl
- compound
- derivatives
- substituted
- 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
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 title abstract 3
- 150000003053 piperidines Chemical class 0.000 title abstract 2
- -1 aliphatic hydrocarbon radical Chemical class 0.000 abstract 7
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 abstract 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- JVQOGYAKCWOIEK-UHFFFAOYSA-N 1-(1-benzofuran-2-yl)piperidine Chemical class C1CCCCN1C1=CC2=CC=CC=C2O1 JVQOGYAKCWOIEK-UHFFFAOYSA-N 0.000 abstract 1
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 150000003935 benzaldehydes Chemical class 0.000 abstract 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical class OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 abstract 1
- 150000003222 pyridines Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- 125000004853 tetrahydropyridinyl group Chemical class N1(CCCC=C1)* 0.000 abstract 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH310373A CH592656A5 (enExample) | 1973-03-02 | 1973-03-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1465581A true GB1465581A (en) | 1977-02-23 |
Family
ID=4248678
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB927974A Expired GB1465581A (en) | 1973-03-02 | 1974-03-01 | Tetrahydropyridine and piperidine derivatives and processes for the preparation thereof |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4210655A (enExample) |
| JP (2) | JPS599557B2 (enExample) |
| AR (4) | AR205619A1 (enExample) |
| AT (1) | AT336014B (enExample) |
| BE (1) | BE811767A (enExample) |
| CA (1) | CA1045139A (enExample) |
| CH (1) | CH592656A5 (enExample) |
| CS (5) | CS176298B2 (enExample) |
| DD (1) | DD113007A5 (enExample) |
| DE (1) | DE2408476A1 (enExample) |
| DK (1) | DK147318C (enExample) |
| ES (1) | ES423711A1 (enExample) |
| FR (1) | FR2219781B1 (enExample) |
| GB (1) | GB1465581A (enExample) |
| HU (1) | HU172464B (enExample) |
| IE (1) | IE38907B1 (enExample) |
| IL (1) | IL44237A (enExample) |
| LU (1) | LU69510A1 (enExample) |
| MX (1) | MX3765E (enExample) |
| NL (1) | NL179206C (enExample) |
| SE (1) | SE410856B (enExample) |
| SU (6) | SU560531A3 (enExample) |
| YU (2) | YU52374A (enExample) |
| ZA (1) | ZA741362B (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0011606A3 (de) * | 1978-11-21 | 1980-07-09 | Ciba-Geigy Ag | Pharmazeutische Präparate mit zentraldämpfender und antipsychotischer Wirksamkeit |
| US4259338A (en) | 1978-06-22 | 1981-03-31 | Ciba-Geigy Corporation | Benzofuranyl-tetrahydropyridines and -piperidines, their acid addition salts and antidepressant preparations thereof |
| GB2311010A (en) * | 1996-03-11 | 1997-09-17 | Merck Sharp & Dohme | Tetrahydropyridine derivatives as dopamine receptor subtype ligands |
| US5708007A (en) * | 1993-08-05 | 1998-01-13 | Hoechst Marion Roussel, Inc. | 2-(piperidin-4-yl, pyridin-4-yl and tetrahydropyridin-4-yl) benzofuran-7-ol and carbamate derivatives for treating memory dysfunction |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH609054A5 (en) * | 1975-11-26 | 1979-02-15 | Ciba Geigy Ag | Process for the preparation of a novel piperidine derivative |
| US5045551A (en) * | 1989-09-19 | 1991-09-03 | Allergan, Inc. | Acetylenes disubstituted with a heteroaromatic group and a 2-substituted chromanyl, thiochromanyl or 1,2,3,4-tetrahydroquinolinyl group having retinoid-like activity |
| US5455254A (en) * | 1991-02-15 | 1995-10-03 | Mondadori; Cesare | Substituted benzofuranylpiperidine as a nootropic agent |
| RU2095339C1 (ru) * | 1991-10-17 | 1997-11-10 | Циба-Гейги АГ | Производные гидрохинона в свободном виде или в виде соли, способы их получения, производные пиперидина и способы их получения |
| JPH07503972A (ja) * | 1992-02-21 | 1995-04-27 | ノバルティス アクチェンゲゼルシャフト | 外傷後のストレスの治療用薬剤としてのブロファロミン |
| US5693807A (en) * | 1992-10-14 | 1997-12-02 | Ciba-Geigy Corporation | Substituted hydroquinone derivatives |
| AU5319700A (en) | 1999-06-02 | 2000-12-18 | S. Mbua Ngale Efange | Nicotine receptor ligands |
| WO2011162364A1 (ja) * | 2010-06-23 | 2011-12-29 | 住友化学株式会社 | 有害節足動物防除組成物および複素環化合物 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1041525A (en) * | 1964-11-11 | 1966-09-07 | Belge Produits Chimiques Sa | Benzofuran derivatives and processes for preparing the same |
| FR1461633A (fr) * | 1964-11-11 | 1966-02-25 | Belge Produits Chimiques Sa | Nouveaux dérivés benzofuranniques, leurs sels et procédés de préparation de cesdérivés et de leurs sels |
| IE39264B1 (en) * | 1973-05-25 | 1978-08-30 | Ciba Geigy Ag | New pharmaceutical preparations |
-
1973
- 1973-03-02 CH CH310373A patent/CH592656A5/xx not_active IP Right Cessation
-
1974
- 1974-01-01 AR AR252581A patent/AR205619A1/es active
- 1974-02-19 IL IL44237A patent/IL44237A/en unknown
- 1974-02-20 IE IE00340/74A patent/IE38907B1/xx unknown
- 1974-02-21 SE SE7402294A patent/SE410856B/xx not_active IP Right Cessation
- 1974-02-22 DE DE19742408476 patent/DE2408476A1/de active Granted
- 1974-02-25 CA CA193,450A patent/CA1045139A/en not_active Expired
- 1974-02-28 FR FR7406834A patent/FR2219781B1/fr not_active Expired
- 1974-02-28 NL NLAANVRAGE7402755,A patent/NL179206C/xx not_active IP Right Cessation
- 1974-02-28 LU LU69510*A patent/LU69510A1/xx unknown
- 1974-02-28 YU YU00523/74A patent/YU52374A/xx unknown
- 1974-02-28 DD DD176867A patent/DD113007A5/xx unknown
- 1974-02-28 HU HU74CI00001456A patent/HU172464B/hu unknown
- 1974-02-28 CS CS8939A patent/CS176298B2/cs unknown
- 1974-02-28 CS CS8940A patent/CS176299B2/cs unknown
- 1974-02-28 SU SU2000455A patent/SU560531A3/ru active
- 1974-02-28 CS CS1495A patent/CS176266B2/cs unknown
- 1974-02-28 CS CS8937A patent/CS176296B2/cs unknown
- 1974-02-28 CS CS8938A patent/CS176297B2/cs unknown
- 1974-02-28 ES ES423711A patent/ES423711A1/es not_active Expired
- 1974-03-01 DK DK110174A patent/DK147318C/da not_active IP Right Cessation
- 1974-03-01 BE BE141551A patent/BE811767A/xx not_active IP Right Cessation
- 1974-03-01 GB GB927974A patent/GB1465581A/en not_active Expired
- 1974-03-01 AT AT170674A patent/AT336014B/de not_active IP Right Cessation
- 1974-03-01 ZA ZA00741362A patent/ZA741362B/xx unknown
- 1974-03-01 MX MX745143U patent/MX3765E/es unknown
- 1974-03-02 JP JP49024715A patent/JPS599557B2/ja not_active Expired
-
1975
- 1975-06-30 AR AR259413A patent/AR208554A1/es active
- 1975-06-30 AR AR259412A patent/AR210858A1/es active
-
1976
- 1976-05-05 AR AR263204A patent/AR211860A1/es active
- 1976-09-24 SU SU762402851A patent/SU651702A3/ru active
- 1976-09-24 SU SU762404754A patent/SU612630A3/ru active
- 1976-09-28 SU SU762404895A patent/SU646911A4/ru active
- 1976-11-02 SU SU762415644A patent/SU649321A3/ru active
-
1977
- 1977-08-24 SU SU772514703A patent/SU651703A3/ru active
-
1978
- 1978-04-05 US US05/893,104 patent/US4210655A/en not_active Expired - Lifetime
-
1980
- 1980-08-25 YU YU02123/80A patent/YU212380A/xx unknown
-
1982
- 1982-06-16 JP JP57102323A patent/JPS6046115B2/ja not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4259338A (en) | 1978-06-22 | 1981-03-31 | Ciba-Geigy Corporation | Benzofuranyl-tetrahydropyridines and -piperidines, their acid addition salts and antidepressant preparations thereof |
| EP0011606A3 (de) * | 1978-11-21 | 1980-07-09 | Ciba-Geigy Ag | Pharmazeutische Präparate mit zentraldämpfender und antipsychotischer Wirksamkeit |
| US4284638A (en) * | 1978-11-21 | 1981-08-18 | Ciba-Geigy Corporation | Pharmaceutical compositions with central depressant and antipsychotic activity having a butyrophenone derivative which is substituted in the 4-position and a C-(2-benzofuranyl)-piperidine or C-(2-benzofuranyl)-tetrahydro-pyridine |
| US5708007A (en) * | 1993-08-05 | 1998-01-13 | Hoechst Marion Roussel, Inc. | 2-(piperidin-4-yl, pyridin-4-yl and tetrahydropyridin-4-yl) benzofuran-7-ol and carbamate derivatives for treating memory dysfunction |
| GB2311010A (en) * | 1996-03-11 | 1997-09-17 | Merck Sharp & Dohme | Tetrahydropyridine derivatives as dopamine receptor subtype ligands |
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19940228 |