GB1364354A - Amino phenyl ketone derivatives processes for producing them and compositions containing them - Google Patents
Amino phenyl ketone derivatives processes for producing them and compositions containing themInfo
- Publication number
- GB1364354A GB1364354A GB1715772A GB1715772A GB1364354A GB 1364354 A GB1364354 A GB 1364354A GB 1715772 A GB1715772 A GB 1715772A GB 1715772 A GB1715772 A GB 1715772A GB 1364354 A GB1364354 A GB 1364354A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- fluoro
- hydrogen
- alkyl
- compound
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Abstract
1364354 Aminophenyl spirocyclic ketones SUMITOMO CHEMICAL CO Ltd 13 April 1972 [15 April 1971 (2)] 17157/72 Heading C2C Novel compounds of Formula I wherein R<SP>1</SP> is hydrogen, C 1 -C 4 alkyl or aryl; R is hydrogen or a group having the formula -CO-R<SP>2</SP> (wherein R<SP>2</SP> is hydrogen, C 1 -C 4 alkyl or aryl); R<SP>3</SP> is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or trifluoromethyl; R<SP>4</SP> is hydrogen, C 1 -C 4 alkyl or C 1 -C 4 alkanoyl; X is carbonyl or methylene; Y is oxygen or a group having the formula wherein R<SP>5</SP> is C 1 -C 4 alkyl or aryl); and Z is a group having the formula (wherein R<SP>6</SP> and R<SP>7</SP> are each hydrogen, C 1 -C 4 alkyl, aryl or aralkyl and R<SP>6</SP> and R<SP>7</SP> may form bivalent C 2 -C 5 alkylene), and acid addition salts thereof are prepared by oxidation of a compound of Formula IV and optionally removing the acyl of the acylamino group by hydrolysis. Intermediates of Formula IV above are prepared either by reduction of a compound of Formula XII or by reaction of a compound of Formula X with a compound of Formula XI Intermediates of Formula XII above are prepared by reaction of the appropriate acid chloride and a compound of Formula XI above. Intermediates of Formula X above are prepared by action of p-toluene sulphonyl chloride and lithium chloride on the propyl alcohol which is obtained by reduction of the indolylpropionic acid obtained by hydrolysis of the appropriate nitrile. # - (6 - Fluoro - 2 - methyl - indolyl) propionitrile is obtained by reacting #-chloropropionitrile with 6-fluoro-2-methyl indole obtained by reductive cyclization of 4-fluoro-2 nitrophenylacetone obtained from (4-fluoro-2-nitrophenyl). acetyl malonic acid diethyl ester obtained in situ from the magnesium ethoxy derivative of diethyl malonate and the acid chloride obtained by the action of thionyl chloride on 4-fluoro-2- nitrophenyl-acetic acid which is prepared by action of alhaline hydrogen peroxide on ethyl 4 -fluoro - 2 - nitrophenyl pyrurate obtained from 4 - fluoro - 2 - nitrotoluene and diethyloxulate. Pharmaceutical compositions in conventional forms for oral administration having sedative, anti-depressant, tranquillizing, anti-convulsive, anti-psychotic and analgesic activity comprises an above novel compound or salt and a pharmaceutical carrier or diluent.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP46024376A JPS5136752B1 (en) | 1971-04-15 | 1971-04-15 | |
| JP2437371 | 1971-04-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1364354A true GB1364354A (en) | 1974-08-21 |
Family
ID=26361874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1715772A Expired GB1364354A (en) | 1971-04-15 | 1972-04-13 | Amino phenyl ketone derivatives processes for producing them and compositions containing them |
Country Status (19)
| Country | Link |
|---|---|
| AR (1) | AR199993A1 (en) |
| AU (1) | AU442844B2 (en) |
| BE (1) | BE782098A (en) |
| CA (1) | CA976168A (en) |
| CH (1) | CH568321A5 (en) |
| CS (1) | CS179967B2 (en) |
| DD (1) | DD98682A5 (en) |
| DE (1) | DE2218190B2 (en) |
| DK (1) | DK139300B (en) |
| ES (1) | ES401724A1 (en) |
| FI (1) | FI53820C (en) |
| FR (1) | FR2133610B1 (en) |
| GB (1) | GB1364354A (en) |
| IL (1) | IL39204A (en) |
| NL (1) | NL7205038A (en) |
| NO (1) | NO134744C (en) |
| PL (1) | PL88960B1 (en) |
| SE (1) | SE379355B (en) |
| SU (1) | SU515451A3 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2416397C1 (en) * | 2009-11-09 | 2011-04-20 | Общество с ограниченной ответственностью "Лечебно-реабилитационный научный центр "Феникс" | Method of treating depression, resistant to psychopharmacothery |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI685497B (en) * | 2014-06-02 | 2020-02-21 | 西班牙商伊史帝夫製藥公司 | Alkyl derivatives of 1-oxa-4,9-diazaspiro undecane compounds having multimodal activity against pain |
-
1972
- 1972-04-07 FR FR7212253A patent/FR2133610B1/fr not_active Expired
- 1972-04-11 CH CH532672A patent/CH568321A5/xx not_active IP Right Cessation
- 1972-04-11 NO NO1232/72A patent/NO134744C/no unknown
- 1972-04-12 AU AU41063/72A patent/AU442844B2/en not_active Expired
- 1972-04-12 IL IL39204A patent/IL39204A/en unknown
- 1972-04-12 CA CA139,521A patent/CA976168A/en not_active Expired
- 1972-04-13 ES ES401724A patent/ES401724A1/en not_active Expired
- 1972-04-13 PL PL1972154697A patent/PL88960B1/xx unknown
- 1972-04-13 FI FI1050/72A patent/FI53820C/en active
- 1972-04-13 GB GB1715772A patent/GB1364354A/en not_active Expired
- 1972-04-14 DK DK183472AA patent/DK139300B/en unknown
- 1972-04-14 AR AR241470A patent/AR199993A1/en active
- 1972-04-14 DE DE19722218190 patent/DE2218190B2/en active Granted
- 1972-04-14 SU SU1773176A patent/SU515451A3/en active
- 1972-04-14 SE SE7204889A patent/SE379355B/xx unknown
- 1972-04-14 CS CS7200002535A patent/CS179967B2/en unknown
- 1972-04-14 NL NL7205038A patent/NL7205038A/xx not_active Application Discontinuation
- 1972-04-14 DD DD162302A patent/DD98682A5/xx unknown
- 1972-04-14 BE BE782098A patent/BE782098A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2416397C1 (en) * | 2009-11-09 | 2011-04-20 | Общество с ограниченной ответственностью "Лечебно-реабилитационный научный центр "Феникс" | Method of treating depression, resistant to psychopharmacothery |
Also Published As
| Publication number | Publication date |
|---|---|
| FI53820B (en) | 1978-05-02 |
| IL39204A0 (en) | 1972-06-28 |
| CA976168A (en) | 1975-10-14 |
| FR2133610A1 (en) | 1972-12-01 |
| SU515451A3 (en) | 1976-05-25 |
| AU442844B2 (en) | 1973-12-06 |
| DD98682A5 (en) | 1973-07-05 |
| AR199993A1 (en) | 1974-10-15 |
| DK139300C (en) | 1979-07-09 |
| FI53820C (en) | 1978-08-10 |
| FR2133610B1 (en) | 1975-10-31 |
| NO134744B (en) | 1976-08-30 |
| SE379355B (en) | 1975-10-06 |
| BE782098A (en) | 1972-07-31 |
| ES401724A1 (en) | 1975-11-01 |
| CS179967B2 (en) | 1977-12-30 |
| CH568321A5 (en) | 1975-10-31 |
| DE2218190B2 (en) | 1977-01-20 |
| NL7205038A (en) | 1972-10-17 |
| NO134744C (en) | 1976-12-08 |
| IL39204A (en) | 1975-10-15 |
| PL88960B1 (en) | 1976-10-30 |
| DE2218190A1 (en) | 1973-01-25 |
| AU4106372A (en) | 1973-10-18 |
| DK139300B (en) | 1979-01-29 |
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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 |