DD155065A5 - Verfahren zur herstellung von phenylazacycloalkanen - Google Patents
Verfahren zur herstellung von phenylazacycloalkanen Download PDFInfo
- Publication number
- DD155065A5 DD155065A5 DD80225781A DD22578180A DD155065A5 DD 155065 A5 DD155065 A5 DD 155065A5 DD 80225781 A DD80225781 A DD 80225781A DD 22578180 A DD22578180 A DD 22578180A DD 155065 A5 DD155065 A5 DD 155065A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- compound
- group
- carbon atoms
- formula
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 61
- 238000002360 preparation method Methods 0.000 title abstract description 18
- 230000008569 process Effects 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 192
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 62
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 52
- 239000002253 acid Substances 0.000 claims abstract description 30
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 239000007858 starting material Substances 0.000 claims abstract description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 18
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 17
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 16
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 13
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 94
- 239000000203 mixture Substances 0.000 claims description 37
- -1 carboxylic acid halide Chemical class 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 230000009467 reduction Effects 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 239000012948 isocyanate Substances 0.000 claims description 7
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- 150000001412 amines Chemical class 0.000 claims description 5
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- 150000003949 imides Chemical class 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
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- 229940100198 alkylating agent Drugs 0.000 claims description 3
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- VRNBZJJBPKLDAO-UHFFFAOYSA-N 3-(1-propan-2-ylpiperidin-3-yl)phenol Chemical compound C1N(C(C)C)CCCC1C1=CC=CC(O)=C1 VRNBZJJBPKLDAO-UHFFFAOYSA-N 0.000 claims description 2
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- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 claims 1
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- 239000000543 intermediate Substances 0.000 abstract description 7
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- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000803 paradoxical effect Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 210000005215 presynaptic neuron Anatomy 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 210000004129 prosencephalon Anatomy 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000002277 temperature effect Effects 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000007723 transport mechanism Effects 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 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
- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
-
- 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
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- C07D207/08—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 hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Polyamides (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE7910026 | 1979-12-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
DD155065A5 true DD155065A5 (de) | 1982-05-12 |
Family
ID=20339477
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DD80225781A DD155065A5 (de) | 1979-12-05 | 1980-12-05 | Verfahren zur herstellung von phenylazacycloalkanen |
Country Status (17)
Country | Link |
---|---|
US (1) | US4426386A (en16) |
EP (2) | EP0084920B1 (en16) |
JP (1) | JPS6135175B2 (en16) |
AT (1) | ATE42281T1 (en16) |
AU (1) | AU542153B2 (en16) |
CA (1) | CA1147339A (en16) |
DD (1) | DD155065A5 (en16) |
DE (1) | DE3070247D1 (en16) |
DK (1) | DK155793C (en16) |
ES (3) | ES497489A0 (en16) |
FI (1) | FI67371C (en16) |
GR (1) | GR72841B (en16) |
HU (1) | HU185422B (en16) |
IE (1) | IE50674B1 (en16) |
PT (1) | PT72172B (en16) |
SE (1) | SE8107742L (en16) |
WO (1) | WO1981001552A1 (en16) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE8305362D0 (sv) * | 1983-09-30 | 1983-09-30 | Astra Laekemedel Ab | Novel substituted phenylazacycloalkanes, processes for preparation and pharmaceutical preparations for such compounds |
US4937346A (en) * | 1979-12-05 | 1990-06-26 | Per Arvid Emil Carlsson | Phenyl-azacykloalkanes |
SE446335B (sv) * | 1982-03-30 | 1986-09-01 | Astra Laekemedel Ab | Ren enantiomer av en metasubstituerad 3-fenyl-1-propylpiperidin |
EP0077607A1 (en) * | 1981-09-17 | 1983-04-27 | Beecham Group Plc | N-substituted 3-aryl piperidines and derivatives thereof |
US4719219A (en) * | 1982-03-30 | 1988-01-12 | Per A. E. Carlsson | Phenyl-azacycloalkanes and use thereof in treatment of central nervous system disorders |
EP0105243B1 (de) * | 1982-10-01 | 1988-08-03 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Spaltung von rac. 1-Propyl-3-aryl-piperidinen |
US4593037A (en) * | 1984-07-26 | 1986-06-03 | Pfizer Inc. | 1,3-disubstituted piperidine compounds as neuroleptic agents |
JPH0657695B2 (ja) * | 1985-07-12 | 1994-08-03 | エーザイ株式会社 | 4−シアノピペリジン誘導体 |
US4826869A (en) * | 1988-02-19 | 1989-05-02 | Syntex (U.S.A.) Inc. | N-(lower alkyl)-2-(3'ureidobenzyl)pyrrolidines |
DE3930282A1 (de) * | 1989-09-11 | 1991-03-21 | Boehringer Ingelheim Kg | Verwendung von dopamin-autorezeptor-agonisten bei der behandlung von drogenabhaengigkeit |
GB9113031D0 (en) * | 1991-06-17 | 1991-08-07 | Smithkline Beecham Plc | Compounds |
SE9802546D0 (sv) * | 1998-07-15 | 1998-07-15 | Ross Nicholas Waters | Medicinal product and method for treatment and prevention of dyskinesia |
NZ514560A (en) * | 1999-03-31 | 2004-02-27 | Univ Arizona Foundation | Viral treatment |
US7346938B2 (en) * | 2002-08-02 | 2008-03-25 | Roy W. Mattson, Jr. | Retrofit suction sanitation safety cover |
EP1707558A1 (en) * | 2005-03-21 | 2006-10-04 | Ferrer Internacional, S.A. | Benzoic acid ester compounds, compositions, uses and methods related thereto |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2892842A (en) | 1959-06-30 | Their preparation | ||
DE1144279B (de) * | 1957-09-26 | 1963-02-28 | Robins Co Inc A H | Verfahren zur Herstellung von 3-Aryl-3-hydroxypyrrolidinen und deren Salzen |
FR1248129A (fr) * | 1959-02-12 | 1960-12-09 | Mead Johnson & Co | Procédé de préparation des 1-acyl- et 1-carbalkoxy-3 pyrrolidinols |
US2975193A (en) * | 1959-06-18 | 1961-03-14 | Parke Davis & Co | Organic amine compounds and method of obtaining the same |
NO116115B (en16) * | 1962-06-01 | 1969-02-03 | Parke Davis & Co | |
DK104980C (da) * | 1962-06-20 | 1966-08-01 | Parke Davis & Company A Corp O | Fremgangsmåde til fremstilling af optisk aktive eller racemiske 1-methylpyrrolidinderivater eller syreadditionssalte deraf. |
DK105337C (da) * | 1962-06-20 | 1966-09-19 | Parke Davis & Company A Corp O | Fremgangsmåde til fremstilling af optisk aktive eller racemiske pyrrolidinforbindelser eller syreadditionssalte deraf. |
DK104736C (da) * | 1962-06-20 | 1966-06-27 | Parke Davis & Company A Corp O | Fremgangsmåde til fremstilling af optisk aktive eller racemiske pyrrolidin-derivater eller syreadditionssalte deraf. |
DE1470155A1 (de) * | 1963-04-11 | 1969-06-04 | Parke Davis & Co | Neue Pyrrolidinverbindungen,ihre Saeureadditionssalze,sowie Verfahren zu deren Herstellung |
GB1012008A (en) * | 1963-08-01 | 1965-12-01 | Parke Davis & Co | Process for the production of pyrrolidine compounds |
GB1198973A (en) | 1969-02-07 | 1970-07-15 | Parke Davis & Co | Pyrrolidine Compounds with an Unsaturated Substituent and Methods for their Production |
US3647790A (en) * | 1969-04-08 | 1972-03-07 | American Home Prod | Ouinoxalinyl-oxazolidines and -oxazines |
CH526536A (de) * | 1970-02-05 | 1972-08-15 | Sandoz Ag | Verfahren zur Herstellung neuer 3-Phenylpyrrolidinderivate |
GB1283452A (en) * | 1970-07-24 | 1972-07-26 | Parke Davis & Co | Substituted 1,3-dialkylpyrrolidines and processes for their production |
US3970656A (en) * | 1974-06-11 | 1976-07-20 | Government Of The United States | 1-Alkyl-4-m-hydroxyphenyl-4-propionyl piperidines |
FR2310761A1 (fr) | 1975-05-16 | 1976-12-10 | Roussel Uclaf | Nouveaux derives de la phenyl-piperidine et leurs sels, procede de preparation et application a titre de medicaments |
FR2310762A1 (fr) | 1975-05-16 | 1976-12-10 | Roussel Uclaf | Nouveaux derives n-substitues de la phenyl piperidine et leurs sels, procede de preparation et application a titre de medicaments |
DE2701705A1 (de) * | 1976-01-28 | 1977-08-04 | Sandoz Ag | Neue organische verbindungen, ihre verwendung und herstellung |
FR2340734A1 (fr) * | 1976-02-13 | 1977-09-09 | Roussel Uclaf | Nouveaux derives de la m-trifluoromethylphenyl piperidine et leurs sels, procede de preparation et application a titre de medicaments |
FR2380261A2 (fr) * | 1977-02-11 | 1978-09-08 | Roussel Uclaf | Nouveaux derives de la m-trifluoromethylphenylpiperidine et leurs sels, procede de preparation et application a titre de medicaments |
-
1980
- 1980-12-05 AU AU66426/81A patent/AU542153B2/en not_active Ceased
- 1980-12-05 US US06/213,633 patent/US4426386A/en not_active Expired - Lifetime
- 1980-12-05 ES ES497489A patent/ES497489A0/es active Granted
- 1980-12-05 DD DD80225781A patent/DD155065A5/de not_active IP Right Cessation
- 1980-12-05 CA CA000366280A patent/CA1147339A/en not_active Expired
- 1980-12-05 EP EP83200131A patent/EP0084920B1/en not_active Expired
- 1980-12-05 GR GR63561A patent/GR72841B/el unknown
- 1980-12-05 IE IE2545/80A patent/IE50674B1/en not_active IP Right Cessation
- 1980-12-05 AT AT83200131T patent/ATE42281T1/de active
- 1980-12-05 PT PT72172A patent/PT72172B/pt not_active IP Right Cessation
- 1980-12-05 HU HU811212A patent/HU185422B/hu not_active IP Right Cessation
- 1980-12-05 WO PCT/SE1980/000319 patent/WO1981001552A1/en active IP Right Grant
- 1980-12-05 JP JP56500175A patent/JPS6135175B2/ja not_active Expired
- 1980-12-05 DE DE8080850183T patent/DE3070247D1/de not_active Expired
- 1980-12-05 EP EP80850183A patent/EP0030526B1/en not_active Expired
-
1981
- 1981-07-31 DK DK342881A patent/DK155793C/da not_active IP Right Cessation
- 1981-12-16 ES ES508029A patent/ES8300703A1/es not_active Expired
- 1981-12-16 ES ES508030A patent/ES8300092A1/es not_active Expired
- 1981-12-18 FI FI814080A patent/FI67371C/fi not_active IP Right Cessation
- 1981-12-23 SE SE8107742A patent/SE8107742L/xx not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
PT72172A (en) | 1981-01-01 |
FI67371C (fi) | 1985-03-11 |
FI814080L (fi) | 1981-12-18 |
ES508030A0 (es) | 1982-10-01 |
JPS6135175B2 (en16) | 1986-08-12 |
WO1981001552A1 (en) | 1981-06-11 |
US4426386A (en) | 1984-01-17 |
ES8300092A1 (es) | 1982-10-01 |
EP0084920A2 (en) | 1983-08-03 |
AU6642681A (en) | 1981-06-19 |
ES508029A0 (es) | 1982-11-01 |
PT72172B (en) | 1982-07-05 |
HU185422B (en) | 1985-02-28 |
FI67371B (fi) | 1984-11-30 |
IE50674B1 (en) | 1986-06-11 |
EP0030526A1 (en) | 1981-06-17 |
DK342881A (da) | 1981-07-31 |
DK155793C (da) | 1989-10-02 |
ES8300703A1 (es) | 1982-11-01 |
ES8205768A1 (es) | 1982-08-01 |
DE3070247D1 (en) | 1985-04-04 |
JPS56501679A (en16) | 1981-11-19 |
EP0084920A3 (en) | 1985-05-22 |
SE8107742L (sv) | 1981-12-23 |
IE802545L (en) | 1981-06-05 |
EP0084920B1 (en) | 1989-04-19 |
CA1147339A (en) | 1983-05-31 |
AU542153B2 (en) | 1985-02-07 |
ATE42281T1 (de) | 1989-05-15 |
ES497489A0 (es) | 1982-08-01 |
GR72841B (en16) | 1983-12-07 |
EP0030526B1 (en) | 1985-02-27 |
DK155793B (da) | 1989-05-16 |
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