CH643243A5 - Cis- et trans-3-aryloxy-4-hydroxypyrrolidines et leurs derives, utiles notamment en medecine veterinaire comme antidepresseurs. - Google Patents
Cis- et trans-3-aryloxy-4-hydroxypyrrolidines et leurs derives, utiles notamment en medecine veterinaire comme antidepresseurs. Download PDFInfo
- Publication number
- CH643243A5 CH643243A5 CH10280A CH10280A CH643243A5 CH 643243 A5 CH643243 A5 CH 643243A5 CH 10280 A CH10280 A CH 10280A CH 10280 A CH10280 A CH 10280A CH 643243 A5 CH643243 A5 CH 643243A5
- Authority
- CH
- Switzerland
- Prior art keywords
- trans
- benzyl
- pyrrolidinol
- mixture
- cis
- Prior art date
Links
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- 238000000034 method Methods 0.000 claims description 11
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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 claims description 8
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- 229910000104 sodium hydride Inorganic materials 0.000 claims description 7
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- KOYSMNHLBIJMFS-GHMZBOCLSA-N (3r,4r)-1-methyl-4-phenoxypyrrolidin-3-ol Chemical compound C1N(C)C[C@@H](O)[C@@H]1OC1=CC=CC=C1 KOYSMNHLBIJMFS-GHMZBOCLSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 2
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- MYLHABWCUKUROP-GHMZBOCLSA-N (3r,4r)-4-(2,6-dichlorophenoxy)-1-ethylpyrrolidin-3-ol Chemical compound C1N(CC)C[C@@H](O)[C@@H]1OC1=C(Cl)C=CC=C1Cl MYLHABWCUKUROP-GHMZBOCLSA-N 0.000 claims 1
- ZXIDMMHTXZOWDR-RKDXNWHRSA-N (3r,4r)-4-(2,6-dichlorophenoxy)pyrrolidin-3-ol Chemical compound O[C@@H]1CNC[C@H]1OC1=C(Cl)C=CC=C1Cl ZXIDMMHTXZOWDR-RKDXNWHRSA-N 0.000 claims 1
- JIPSFMGFOPJSJR-ZYHUDNBSSA-N (3r,4r)-4-(2-chlorophenoxy)-1-ethylpyrrolidin-3-ol Chemical compound C1N(CC)C[C@@H](O)[C@@H]1OC1=CC=CC=C1Cl JIPSFMGFOPJSJR-ZYHUDNBSSA-N 0.000 claims 1
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- DMFMZFFIQRMJQZ-UHFFFAOYSA-N pyrrolidin-1-ium;iodide Chemical compound [I-].C1CC[NH2+]C1 DMFMZFFIQRMJQZ-UHFFFAOYSA-N 0.000 claims 1
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- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000005303 weighing 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
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D207/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US215179A | 1979-01-09 | 1979-01-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH643243A5 true CH643243A5 (fr) | 1984-05-30 |
Family
ID=21699450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH10280A CH643243A5 (fr) | 1979-01-09 | 1980-01-08 | Cis- et trans-3-aryloxy-4-hydroxypyrrolidines et leurs derives, utiles notamment en medecine veterinaire comme antidepresseurs. |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5598160A (en, 2012) |
| CA (1) | CA1133495A (en, 2012) |
| CH (1) | CH643243A5 (en, 2012) |
| DE (1) | DE3000625A1 (en, 2012) |
| FR (1) | FR2446279B1 (en, 2012) |
| GB (1) | GB2040933B (en, 2012) |
| IT (1) | IT1127967B (en, 2012) |
| MX (1) | MX6634E (en, 2012) |
| SE (1) | SE435927B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE45511B1 (en) | 1976-09-01 | 1982-09-08 | Ciba Geigy Ag | New derivatives of perhydro-aza-heterocycles and processesfor the production thereof |
| US4547514A (en) * | 1983-12-05 | 1985-10-15 | A. H. Robins Company, Incorporated | Aryloxy-N-(aminoalkyl)-1-pyrrolidine and piperidine carboxamides and carbothioamides having antiarrhythmic activity |
| JPS60178860A (ja) * | 1984-02-24 | 1985-09-12 | Sankyo Co Ltd | ３−メルカプトピロリジンまたはその塩の製法 |
| JPS6157552A (ja) * | 1984-08-29 | 1986-03-24 | Toyama Chem Co Ltd | ３−アミノピロリジンまたはその塩の製法 |
| DE3813416A1 (de) * | 1988-04-21 | 1989-11-02 | Hoechst Ag | 3,4-dihydroxypyrrolidin-2-on-derivate, verfahren zu ihrer herstellung, diese enthaltende mittel und ihre verwendung sowie die bei der herstellung anfallenden neuen zwischenprodukte |
| EP0407701A3 (en) * | 1989-05-15 | 1992-04-22 | Fujisawa Pharmaceutical Co., Ltd. | Antiretroviral pyrroline and pyrrolidine sulfonic acid derivatives |
| WO2008150470A1 (en) | 2007-05-31 | 2008-12-11 | Shionogi & Co., Ltd. | Oxyimino compounds and the use thereof |
| US8518934B2 (en) | 2008-06-11 | 2013-08-27 | Shonogi & Co., Ltd. | Oxycarbamoyl compounds and the use thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1000308A (fr) * | 1949-05-28 | 1952-02-11 | Basf Ag | Procédé pour la production de 3. 4-dioxypyrrolidines |
| FR1000310A (fr) * | 1949-06-18 | 1952-02-11 | Basf Ag | Procédé pour la production de dérivés de pyrrolidine |
| FR1532221A (fr) * | 1963-10-22 | 1968-07-12 | Robins Co Inc A H | Procédé de production de n, n-di (aryl monocarbocyclique)-carbamates de 1-(alkylinférieur)-3-pyrrolidyle |
| CH521338A (de) * | 1967-03-13 | 1972-04-15 | Robins Co Inc A H | Verfahren zur Herstellung von neuen Pyrrolidinderivaten |
| US3577415A (en) * | 1968-12-23 | 1971-05-04 | Robins Co Inc A H | 1-substituted-3-substituted phenoxypyrrolidines |
| IE45511B1 (en) * | 1976-09-01 | 1982-09-08 | Ciba Geigy Ag | New derivatives of perhydro-aza-heterocycles and processesfor the production thereof |
-
1980
- 1980-01-03 MX MX808576U patent/MX6634E/es unknown
- 1980-01-07 SE SE8000085A patent/SE435927B/sv not_active IP Right Cessation
- 1980-01-08 FR FR8000272A patent/FR2446279B1/fr not_active Expired
- 1980-01-08 IT IT67020/80A patent/IT1127967B/it active
- 1980-01-08 CH CH10280A patent/CH643243A5/fr not_active IP Right Cessation
- 1980-01-09 CA CA343,328A patent/CA1133495A/en not_active Expired
- 1980-01-09 DE DE19803000625 patent/DE3000625A1/de active Granted
- 1980-01-09 GB GB8000709A patent/GB2040933B/en not_active Expired
- 1980-01-09 JP JP123280A patent/JPS5598160A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| SE8000085L (sv) | 1980-08-26 |
| CA1133495A (en) | 1982-10-12 |
| GB2040933B (en) | 1983-07-20 |
| SE435927B (sv) | 1984-10-29 |
| JPS5598160A (en) | 1980-07-25 |
| DE3000625C2 (en, 2012) | 1989-04-20 |
| FR2446279A1 (fr) | 1980-08-08 |
| IT8067020A0 (it) | 1980-01-08 |
| MX6634E (es) | 1985-09-12 |
| IT1127967B (it) | 1986-05-28 |
| GB2040933A (en) | 1980-09-03 |
| JPS648621B2 (en, 2012) | 1989-02-14 |
| DE3000625A1 (de) | 1980-07-17 |
| FR2446279B1 (fr) | 1985-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |