GB1086530A - 4-phenyl and 4-substituted phenyl bicyclo[2,2,2]octane-amines - Google Patents
4-phenyl and 4-substituted phenyl bicyclo[2,2,2]octane-aminesInfo
- Publication number
- GB1086530A GB1086530A GB2031565A GB2031565A GB1086530A GB 1086530 A GB1086530 A GB 1086530A GB 2031565 A GB2031565 A GB 2031565A GB 2031565 A GB2031565 A GB 2031565A GB 1086530 A GB1086530 A GB 1086530A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- bicyclo
- group
- octane
- amino
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/033—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/39—Unsaturated compounds containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention comprises compounds of the formula <FORM:1086530/C2/1> in which R and R1 each represents a hydrogen atom or a C1- 4 alkyl or allyl group, or together form a -(CH2)ngroup where n is 4, 5 or 6, and X and Y each represents a hydrogen, chlorine, bromine or fluorine atom or a methyl, ethyl, cyano, trifluoromethyl, hydroxy, nitro, amino C1- 4 alkylamino, di(C1- 4 alkyl)amino, carboxy or methoxy- or ethoxy-carbonyl group; and their acid addition salts with acids having non-toxic anions. The compounds are prepared by (a) hydrolysing or reducing corresponding 1-acylamino-4-phenyl-bicyclo[2,2,2]-octanes to form the corresponding 1-amino or 1-alkylamino compounds, or (b) ammonolysing or aminolysing methane sulphonic esters of 4-hydroxy -4-phenyl-bicyclo[2,2,2]octanes, or (c) reducing 4 - phenyl - bicyclo[2,2,2]oct - 2 - ene-1 -carboxylic acids or their esters to yield 4-phenyl - bicyclo[2,2,2]octane - 1 - carboxylic acids or esters, if necessary saponifying the esters to the free acids, and converting the acids by the Hofmann, Curtius or Schmidt reaction to 4-phenyl - bicyclo[2,2,2]octane - 1 - amines, or (d) alkylation of 4-phenyl-bicyclo[2,2,2]octane-1 -amines or -alkylamines, e.g. by reaction of alkyl halides or dialkyl sulphates in the presence of a base, or by acylation followed by reduction with lithium aluminium hydride of the resulting N -acyl-amine or N -acyl-N -alkylamine. In a modification of process (d), compounds of Formula I in which R and R1 together form the divalent group -(CH2)nare made by reacting the primary amine with a dicarboxylic acid anhydride to form a corresponding N carboxyacyl-amine which is reduced and cyclized with lithium aluminium hydride. Starting materials.-1-Acetamido-4-phenyl-bicyclo[2,2,2,]octane is prepared by reacting 4-hydroxy - 1 - phenyl - bicyclo[2,2,2]octan - 2-one with hydrazine to form the corresponding hydrazone, heating this with hydrazine, diethylene glycol and potassium hydroxide to form 4 - phenyl - bicyclo[2,2,2]octan - 1 - ol and reacting this with acetonitrile. 1-Acylamino-4-(substituted phenyl)-bicyclo[2,2,2]octanes are prepared by nitrating a 1-acylamino-4-phenyl-bicyclo[2,2,2]octane, reducing the nitro compound to the corresponding amino compound, diazotizing the amino compound and replacing the diazo group in the resulting compound by a hydroxy group by heating it in an aqueous solution or by a halogen atom or cyano group by reacting it with a cuprous halide or cuprous cyanide. A resulting phenol may be alkylated to give the corresponding alkoxy compound, or a resulting nitrile may be hydrolysed to the corresponding carboxylic acid which may be converted to an ester or reacted with sulphur tetrafluoride to replace the carboxy group by a trifluoromethyl group. If, instead of diazotization, the amino group is acylated and reduced with lithium aluminium hydride the corresponding mono- and di-alkylamino compounds are prepared. Pharmaceutical compositions having anti-depressant activity, for oral or parenteral administration, comprise a compound of the invention together with a pharmaceutical carrier.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR27260A FR5400M (en) | 1965-08-04 | 1965-08-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1086530A true GB1086530A (en) | 1967-10-11 |
Family
ID=8586041
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2031565A Expired GB1086530A (en) | 1965-08-04 | 1965-05-13 | 4-phenyl and 4-substituted phenyl bicyclo[2,2,2]octane-amines |
Country Status (2)
Country | Link |
---|---|
FR (1) | FR5400M (en) |
GB (1) | GB1086530A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015077611A1 (en) | 2013-11-21 | 2015-05-28 | Marquette University | Substituted (4'-hydroxyphenyl)cycloalkane compounds and uses thereof as selective agonists of the estrogen receptor beta isoform |
-
1965
- 1965-05-13 GB GB2031565A patent/GB1086530A/en not_active Expired
- 1965-08-04 FR FR27260A patent/FR5400M/fr not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015077611A1 (en) | 2013-11-21 | 2015-05-28 | Marquette University | Substituted (4'-hydroxyphenyl)cycloalkane compounds and uses thereof as selective agonists of the estrogen receptor beta isoform |
JP2017504567A (en) * | 2013-11-21 | 2017-02-09 | マーケット ユニバーシティー | Substituted (4'-hydroxyphenyl) cycloalkane compounds and their use as selective agonists of estrogen receptor beta isoforms |
AU2014352830B2 (en) * | 2013-11-21 | 2018-12-13 | Concordia University, Inc. | Substituted (4'-hydroxyphenyl)cycloalkane compounds and uses thereof as selective agonists of the estrogen receptor beta isoform |
US10570077B2 (en) | 2013-11-21 | 2020-02-25 | Marquette University | Substituted (4'-hydroxyphenyl)cyclohexane compounds and uses thereof as selective agonists of the estrogen receptor beta isoform |
Also Published As
Publication number | Publication date |
---|---|
FR5400M (en) | 1967-09-25 |
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