GB1530804A - Derivatives of 1-(p-bromophenyl)-1-(3-pyridyl)propene and propane - Google Patents

Derivatives of 1-(p-bromophenyl)-1-(3-pyridyl)propene and propane

Info

Publication number
GB1530804A
GB1530804A GB47800/75A GB4780075A GB1530804A GB 1530804 A GB1530804 A GB 1530804A GB 47800/75 A GB47800/75 A GB 47800/75A GB 4780075 A GB4780075 A GB 4780075A GB 1530804 A GB1530804 A GB 1530804A
Authority
GB
United Kingdom
Prior art keywords
compound
formula
acid
bromophenyl
pyridyl
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
Application number
GB47800/75A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Astra Lakemedel AB
Original Assignee
Astra Lakemedel AB
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Astra Lakemedel AB filed Critical Astra Lakemedel AB
Publication of GB1530804A publication Critical patent/GB1530804A/en
Expired legal-status Critical Current

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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
    • 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
    • C07D213/26—Radicals substituted by halogen atoms or nitro 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
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • 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
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic 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
    • C07D213/54—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
    • C07D213/55—Acids; Esters
    • 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
    • C07D213/54—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
    • C07D213/56—Amides
    • 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
    • C07D213/54—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
    • C07D213/57—Nitriles

Abstract

The Z-isomer of 3-(4-bromophenyl)-N-methyl-3-(3-pyridyl)-allylamine of the formula (I) <IMAGE> or one of its pharmaceutically acceptable acid addition salts exhibits a highly selective inhibitor action on the neuronal uptake of 5-hydroxytryptamine and can be used as an antidepressant or neuroleptic. The said compound is prepared by dehydrating a compound of the formula (II) <IMAGE> and recrystallising the resulting stereoisomer mixture repeatedly from a solvent in which the two E- and Z-isomers show a substantially different solubility. The pure Z-isomer is isolated. The dehydration is preferably carried out with sulphuric acid, hydrochloric acid, phosphoric acid, potassium hydrogen sulphate or oxalic acid, especially by heating, or by catalytic dehydration by treatment with kaolin, mineral alumina or aluminium oxide, especially at a temperature of 300 to 500 DEG C. Preferably, the compound of the formula (I) is recrystallised three times as the oxalate from ethanol.
GB47800/75A 1974-11-21 1975-11-20 Derivatives of 1-(p-bromophenyl)-1-(3-pyridyl)propene and propane Expired GB1530804A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SE7414622A SE388854B (en) 1974-11-21 1974-11-21 PROCEDURE FOR THE PREPARATION OF PHENYLPYRIDYLAMINE DERIVATIVES

Publications (1)

Publication Number Publication Date
GB1530804A true GB1530804A (en) 1978-11-01

Family

ID=20322772

Family Applications (1)

Application Number Title Priority Date Filing Date
GB47800/75A Expired GB1530804A (en) 1974-11-21 1975-11-20 Derivatives of 1-(p-bromophenyl)-1-(3-pyridyl)propene and propane

Country Status (26)

Country Link
JP (1) JPS5176278A (en)
AR (2) AR211921A1 (en)
AT (1) AT346328B (en)
AU (1) AU501915B2 (en)
BE (1) BE835802A (en)
CA (1) CA1056834A (en)
CH (4) CH614937A5 (en)
DD (1) DD122528A5 (en)
DE (1) DE2550005A1 (en)
DK (1) DK147179C (en)
ES (4) ES442758A1 (en)
FI (1) FI61484C (en)
FR (1) FR2291751A1 (en)
GB (1) GB1530804A (en)
HU (1) HU171206B (en)
IE (1) IE42615B1 (en)
IL (1) IL48409A (en)
LU (1) LU73844A1 (en)
NL (1) NL7513648A (en)
NO (1) NO149775C (en)
NZ (1) NZ179247A (en)
PL (2) PL103999B1 (en)
SE (1) SE388854B (en)
SU (1) SU686614A3 (en)
YU (1) YU39153B (en)
ZA (1) ZA756893B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0037163A2 (en) * 1980-02-20 1981-10-07 Philip Morris Incorporated Flavouring agents, smoking compositions, combustible articles and foodstuffs containing such agents, and a method of producing the same
EP0052969A2 (en) * 1980-11-07 1982-06-02 Philip Morris Incorporated Flavorant compounds, their pyrolysis products, and smoking and food compositions containing them
US4418065A (en) 1979-11-16 1983-11-29 Astra Lakemedel Aktiebolag Halophenyl-pyridyl-allylamine derivatives and use

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2857020A1 (en) * 1977-07-04 1981-01-08 Astra Laekemedel Ab A NOVEL INTERMEDIATE FOR PREPARATION OF THERAPEUTICALLY ACTIVE PYRIDINE COMPOUNDS
SE409860B (en) * 1977-07-04 1979-09-10 Astra Laekemedel Ab A NEW INTERMEDIATE PRODUCT FOR THE PREPARATION OF THERAPEUTICALLY ACTIVE PYRIDINE COMPOUNDS
CA1150269A (en) * 1980-11-14 1983-07-19 Carl B. J. Ulff Process for preparing 3-(4-bromophenyl)-3-(3-pyridyl)-allylamines

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH83A (en) * 1888-11-17 1889-01-10 Fontainemelon Horlogerie Improvements made to the construction of watches of all calibers

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4418065A (en) 1979-11-16 1983-11-29 Astra Lakemedel Aktiebolag Halophenyl-pyridyl-allylamine derivatives and use
EP0037163A2 (en) * 1980-02-20 1981-10-07 Philip Morris Incorporated Flavouring agents, smoking compositions, combustible articles and foodstuffs containing such agents, and a method of producing the same
EP0037163A3 (en) * 1980-02-20 1981-12-02 Philip Morris Incorporated Flavouring agents, smoking compositions, combustible articles and foodstuffs containing such agents, and a method of producing the same
EP0052969A2 (en) * 1980-11-07 1982-06-02 Philip Morris Incorporated Flavorant compounds, their pyrolysis products, and smoking and food compositions containing them
EP0052969A3 (en) * 1980-11-07 1982-08-11 Philip Morris Incorporated Flavorant compounds, their pyrolysis products, and smoking and food compositions containing them

Also Published As

Publication number Publication date
IL48409A0 (en) 1976-01-30
AT346328B (en) 1978-11-10
BE835802A (en) 1976-05-21
SU686614A1 (en) 1979-09-15
AR211921A1 (en) 1978-04-14
NO149775C (en) 1984-06-20
PL103999B1 (en) 1979-07-31
ES442758A1 (en) 1977-04-01
FR2291751B1 (en) 1979-09-21
AR210517A1 (en) 1977-08-15
CA1056834A (en) 1979-06-19
JPS5176278A (en) 1976-07-01
PL103784B1 (en) 1979-07-31
SE388854B (en) 1979-03-26
NL7513648A (en) 1976-05-25
ES452171A1 (en) 1977-10-01
NO753849L (en) 1976-05-24
FR2291751A1 (en) 1976-06-18
IL48409A (en) 1979-10-31
CH626066A5 (en) 1981-10-30
YU39153B (en) 1984-06-30
ZA756893B (en) 1976-10-27
CH615665A5 (en) 1980-02-15
IE42615B1 (en) 1980-09-10
NZ179247A (en) 1978-03-06
LU73844A1 (en) 1976-09-06
SU686614A3 (en) 1979-09-15
AU8662775A (en) 1977-05-19
YU293975A (en) 1982-08-31
FI61484B (en) 1982-04-30
AU501915B2 (en) 1979-07-05
DK147179B (en) 1984-05-07
DK518175A (en) 1976-05-22
ES452172A1 (en) 1977-10-01
FI753260A (en) 1976-05-22
DD122528A5 (en) 1976-10-12
DK147179C (en) 1984-11-19
IE42615L (en) 1976-05-21
NO149775B (en) 1984-03-12
CH626065A5 (en) 1981-10-30
HU171206B (en) 1977-12-28
DE2550005A1 (en) 1976-05-26
ATA882275A (en) 1978-03-15
FI61484C (en) 1982-08-10
SE7414622L (en) 1976-05-24
CH614937A5 (en) 1979-12-28
ES452173A1 (en) 1977-10-01

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee