SE435927B - Trans-4-(2-klorofenoxi)-1-etyl-pyrrolidinol med terapeutisk verkan - Google Patents
Trans-4-(2-klorofenoxi)-1-etyl-pyrrolidinol med terapeutisk verkanInfo
- Publication number
- SE435927B SE435927B SE8000085A SE8000085A SE435927B SE 435927 B SE435927 B SE 435927B SE 8000085 A SE8000085 A SE 8000085A SE 8000085 A SE8000085 A SE 8000085A SE 435927 B SE435927 B SE 435927B
- Authority
- SE
- Sweden
- Prior art keywords
- trans
- ethyl
- pyrrolidinol
- chlorophenoxy
- therapeutic effect
- Prior art date
Links
- -1 2-CHLOROPHENOXY Chemical class 0.000 title description 5
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 2
- 230000001430 anti-depressive effect Effects 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 2
- 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
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 230000003288 anthiarrhythmic effect Effects 0.000 claims 1
- 230000003276 anti-hypertensive effect Effects 0.000 claims 1
- 239000000935 antidepressant agent Substances 0.000 claims 1
- 229940005513 antidepressants Drugs 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 150000003235 pyrrolidines Chemical class 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 2
- WZDUNDJSSXEPAS-UHFFFAOYSA-N 3-ethyl-6-oxa-3-azabicyclo[3.1.0]hexane Chemical compound C1N(CC)CC2OC21 WZDUNDJSSXEPAS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 150000003891 oxalate salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 1
- XKTRSTQLVUNLBA-MBORUXJMSA-N (3r,4r)-1-ethyl-4-phenoxypyrrolidin-3-ol;oxalic acid;hydrate Chemical class O.OC(=O)C(O)=O.C1N(CC)C[C@@H](O)[C@@H]1OC1=CC=CC=C1 XKTRSTQLVUNLBA-MBORUXJMSA-N 0.000 description 1
- MECYPUPCCKBGSU-NDXYWBNTSA-N (3r,4r)-4-(2,6-dichlorophenoxy)-1-ethylpyrrolidin-3-ol;hydrochloride Chemical compound Cl.C1N(CC)C[C@@H](O)[C@@H]1OC1=C(Cl)C=CC=C1Cl MECYPUPCCKBGSU-NDXYWBNTSA-N 0.000 description 1
- JHFAGQNTDUJDRD-MHDYBILJSA-N (3r,4r)-4-(2-chlorophenoxy)-1-ethylpyrrolidin-3-ol;hydrochloride Chemical compound Cl.C1N(CC)C[C@@H](O)[C@@H]1OC1=CC=CC=C1Cl JHFAGQNTDUJDRD-MHDYBILJSA-N 0.000 description 1
- ONQBOTKLCMXPOF-UHFFFAOYSA-N 1-ethylpyrrolidine Chemical compound CCN1CCCC1 ONQBOTKLCMXPOF-UHFFFAOYSA-N 0.000 description 1
- RDPWBWXKWOYYID-UHFFFAOYSA-N 3-ethyl-6-oxa-3-azabicyclo[3.1.0]hexane;oxalic acid Chemical compound OC(=O)C(O)=O.C1N(CC)CC2OC21 RDPWBWXKWOYYID-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XLUXHEZIGIDTCC-UHFFFAOYSA-N acetonitrile;ethyl acetate Chemical compound CC#N.CCOC(C)=O XLUXHEZIGIDTCC-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960005333 tetrabenazine Drugs 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)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (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 (2)
| Publication Number | Publication Date |
|---|---|
| SE8000085L SE8000085L (sv) | 1980-08-26 |
| SE435927B true SE435927B (sv) | 1984-10-29 |
Family
ID=21699450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8000085A SE435927B (sv) | 1979-01-09 | 1980-01-07 | Trans-4-(2-klorofenoxi)-1-etyl-pyrrolidinol med terapeutisk verkan |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5598160A (en]) |
| CA (1) | CA1133495A (en]) |
| CH (1) | CH643243A5 (en]) |
| DE (1) | DE3000625A1 (en]) |
| FR (1) | FR2446279B1 (en]) |
| GB (1) | GB2040933B (en]) |
| IT (1) | IT1127967B (en]) |
| MX (1) | MX6634E (en]) |
| SE (1) | SE435927B (en]) |
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 |
| EP2164325B1 (en) | 2007-05-31 | 2013-04-24 | Shionogi&Co., Ltd. | Oxyimino compounds and the use thereof |
| ES2408159T3 (es) * | 2008-06-11 | 2013-06-18 | Shionogi & Co., Ltd. | Compuestos de oxicarbamoilo y su utilización |
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 IT IT67020/80A patent/IT1127967B/it active
- 1980-01-08 FR FR8000272A patent/FR2446279B1/fr not_active Expired
- 1980-01-08 CH CH10280A patent/CH643243A5/fr not_active IP Right Cessation
- 1980-01-09 JP JP123280A patent/JPS5598160A/ja active Granted
- 1980-01-09 GB GB8000709A patent/GB2040933B/en not_active Expired
- 1980-01-09 DE DE19803000625 patent/DE3000625A1/de active Granted
- 1980-01-09 CA CA343,328A patent/CA1133495A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB2040933B (en) | 1983-07-20 |
| CH643243A5 (fr) | 1984-05-30 |
| JPS648621B2 (en]) | 1989-02-14 |
| FR2446279A1 (fr) | 1980-08-08 |
| DE3000625C2 (en]) | 1989-04-20 |
| FR2446279B1 (fr) | 1985-10-31 |
| SE8000085L (sv) | 1980-08-26 |
| IT8067020A0 (it) | 1980-01-08 |
| JPS5598160A (en) | 1980-07-25 |
| CA1133495A (en) | 1982-10-12 |
| IT1127967B (it) | 1986-05-28 |
| DE3000625A1 (de) | 1980-07-17 |
| MX6634E (es) | 1985-09-12 |
| GB2040933A (en) | 1980-09-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
Ref document number: 8000085-4 Effective date: 19920806 Format of ref document f/p: F |