IE35599B1 - 2-phenylbenzoxazoles and their production and use - Google Patents
2-phenylbenzoxazoles and their production and useInfo
- Publication number
- IE35599B1 IE35599B1 IE1136/71A IE113671A IE35599B1 IE 35599 B1 IE35599 B1 IE 35599B1 IE 1136/71 A IE1136/71 A IE 1136/71A IE 113671 A IE113671 A IE 113671A IE 35599 B1 IE35599 B1 IE 35599B1
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- compounds
- hydrogen
- prepared
- phenyl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/39—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups
- C07C205/42—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/43—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1352723 2-Phenyl-benzoxazoles MERCK & CO Inc 6 Sept 1971 [10 Sept 1970 22 July 1971] 41499/71 Heading C2C Novel compounds of Formula (I) and esters, amides and pharmaceutically acceptable salts of those compounds in which R 4 is carboxy, in which formula R<SP>1</SP>α is hydrogen, methyl or fluoro, Rα is hydrogen, methyl, ethyl, allyl, halomethyl or trihalomethyl or Rα and R<SP>1</SP>α together are alkylidene or R<SP>1</SP>α can be a methylene linkage attached to the unsubstituted ortho position of the benzenoid ring, R 2 , R 3 , X and Y are hydrogen alkyl, trihaloalkyl, halo, mercapto, alkylthio, alkylsulphinyl, alkylsulphonyl, nitro, amino, alkylamino, dialkylamino, cyano, carboxy, C 1-6 acyl or dialkyl sulphamyl in which each said alkyl group has 1 to 5 C atoms and R 4 is CH 2 OH or COOH (with the proviso that R<SP>1</SP>α, Rα, R 2 , R 3 , X and Y are not all hydrogen) are prepared by reacting an alkyl phenyl benzoxazole of general Formula (II) in which Rα is hydrogen methyl, ethyl, allyl, halomethyl or trihalomethyl with N-bromo succinimide in refluxing carbon tetrachloride to produce the corresponding bromo-alkylphenyl benzoxazole, treating the latter with sodium cyanide in a suitable solvent to produce the corresponding cyanoalkyl phenyl benzoxazole and subjecting the latter to acid hydrolysis to form a compound of Formula (I) followed by optionally reducing, esterifying, amidating, or neutralizing the compound. Compounds of Formula (I) in which Rα and R<SP>1</SP>α are methylidene are prepared by reacting p-chlorocarbonyl atropamide with an o-amino phenol to produce the corresponding 4-(1-carboxamidovinyl)-2<SP>1</SP>-hydroxy benzanilide, heating the latter at a temperature above its melting point to bring about ring closure to form a compound of general Formula (V) Compounds of general Formula (II) are prepared in a similar manner. Other methods of ring closure used to form compounds of Formula (I) include the oxime rearrangement. Compounds of Formula (I) may also be prepared from 2- phenylbenzoxazoles via the malonic ester or acid derivative, using the Friedel Crafts reaction, by oxidative procedures or fluorination in the phenyl ring. Compounds of Formula (I) are useful in the treatment of inflammations and also exhibit anti-pyretic and analgesic activity and form a pharmaceutical preparation, with a suitable carrier, which may be administered orally, parenterally, topically or rectally.
[GB1352723A]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7122770A | 1970-09-10 | 1970-09-10 | |
| US16538971A | 1971-07-22 | 1971-07-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE35599L IE35599L (en) | 1972-03-10 |
| IE35599B1 true IE35599B1 (en) | 1976-03-31 |
Family
ID=26751978
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1136/71A IE35599B1 (en) | 1970-09-10 | 1971-09-07 | 2-phenylbenzoxazoles and their production and use |
Country Status (23)
| Country | Link |
|---|---|
| JP (2) | JPS544953B1 (en) |
| AT (1) | AT311964B (en) |
| AU (1) | AU461109B2 (en) |
| BE (1) | BE772395A (en) |
| CH (1) | CH572916A5 (en) |
| DD (1) | DD94814A5 (en) |
| DE (1) | DE2145203C2 (en) |
| EG (1) | EG10421A (en) |
| FI (1) | FI55196C (en) |
| FR (1) | FR2106434B1 (en) |
| GB (1) | GB1352723A (en) |
| IE (1) | IE35599B1 (en) |
| IL (1) | IL37633A (en) |
| LU (1) | LU63887A1 (en) |
| NL (1) | NL174043C (en) |
| NO (1) | NO136712C (en) |
| OA (1) | OA03911A (en) |
| PH (1) | PH11935A (en) |
| PL (1) | PL81813B1 (en) |
| RO (1) | RO61539A (en) |
| SE (1) | SE367203B (en) |
| SU (1) | SU455542A3 (en) |
| YU (1) | YU34689B (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3816443A (en) * | 1972-02-17 | 1974-06-11 | Merck & Co Inc | 4-(benzothiazol-2-yl)fluoro phenyl-acetic acids |
| GB1435721A (en) * | 1972-05-18 | 1976-05-12 | Lilly Industries Ltd | Benzoxazole derivatives |
| US3888864A (en) | 1973-06-29 | 1975-06-10 | Hoffmann La Roche | Amino lower alkyl ether derivatives of opium alkaloids |
| GB1495488A (en) * | 1976-06-23 | 1977-12-21 | Ippco Int Pharma Patents Co Es | Optically active 2-(2-phenyl-5-benzoxazolyl)propionic acids |
| IT1099589B (en) * | 1978-08-04 | 1985-09-18 | Ravizza Spa | PROCESS FOR THE PREPARATION OF PROPIONIC BENZOXAZOLYL ACID DERIVATIVES |
| IT1157295B (en) * | 1982-07-19 | 1987-02-11 | Ravizza Spa | PROCESS PERFECTED FOR THE PREPARATION OF DERIVATIVES OF BENZOXAZOLYL PROPIONIC ACID |
| DE19808261A1 (en) * | 1998-02-27 | 1999-10-28 | Bayer Ag | Arylphenyl substituted cyclic ketoenols |
| WO2008035359A2 (en) * | 2006-06-12 | 2008-03-27 | Cadila Healthcare Limited | Oximinophenoxyalkanoic acid and phenylalkanoic acid derivatives |
| JP2008232573A (en) * | 2007-03-22 | 2008-10-02 | Osaka Gas Co Ltd | Absorption refrigerating machine |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD70880A (en) * | ||||
| CH483276A (en) * | 1959-09-23 | 1969-12-31 | Ciba Geigy | Use of 2-phenyl-benzazoles as a protective agent against ultraviolet radiation outside the textile industry |
| US3401120A (en) * | 1965-10-23 | 1968-09-10 | Gaf Corp | Corrosion inhibitors |
| CH514616A (en) * | 1968-10-07 | 1971-10-31 | Ciba Geigy Ag | Process for the preparation of arylene oxazoles |
-
1971
- 1971-09-01 IL IL37633A patent/IL37633A/en unknown
- 1971-09-02 AU AU33024/71A patent/AU461109B2/en not_active Expired
- 1971-09-02 OA OA54349A patent/OA03911A/en unknown
- 1971-09-03 CH CH1295571A patent/CH572916A5/xx not_active IP Right Cessation
- 1971-09-06 PH PH12818A patent/PH11935A/en unknown
- 1971-09-06 GB GB4149971A patent/GB1352723A/en not_active Expired
- 1971-09-06 AT AT773871A patent/AT311964B/en not_active IP Right Cessation
- 1971-09-07 YU YU2279/71A patent/YU34689B/en unknown
- 1971-09-07 IE IE1136/71A patent/IE35599B1/en unknown
- 1971-09-08 PL PL1971150397A patent/PL81813B1/en unknown
- 1971-09-08 EG EG396/71*UA patent/EG10421A/en active
- 1971-09-09 SU SU1696052A patent/SU455542A3/en active
- 1971-09-09 BE BE772395A patent/BE772395A/en not_active IP Right Cessation
- 1971-09-09 DE DE2145203A patent/DE2145203C2/en not_active Expired
- 1971-09-09 FI FI2524/71A patent/FI55196C/en active
- 1971-09-09 SE SE11441/71A patent/SE367203B/xx unknown
- 1971-09-09 LU LU63887D patent/LU63887A1/xx unknown
- 1971-09-09 NL NLAANVRAGE7112437,A patent/NL174043C/en not_active IP Right Cessation
- 1971-09-09 NO NO3355/71A patent/NO136712C/en unknown
- 1971-09-09 DD DD157648A patent/DD94814A5/xx unknown
- 1971-09-10 RO RO68180A patent/RO61539A/ro unknown
- 1971-09-10 JP JP6981371A patent/JPS544953B1/ja active Pending
- 1971-09-10 FR FR7132748A patent/FR2106434B1/fr not_active Expired
-
1977
- 1977-11-02 JP JP52130931A patent/JPS6044304B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| RO61539A (en) | 1976-12-15 |
| DD94814A5 (en) | 1973-01-05 |
| NL7112437A (en) | 1972-03-14 |
| DE2145203C2 (en) | 1984-07-12 |
| FR2106434A1 (en) | 1972-05-05 |
| IE35599L (en) | 1972-03-10 |
| NL174043B (en) | 1983-11-16 |
| CH572916A5 (en) | 1976-02-27 |
| EG10421A (en) | 1976-02-29 |
| JPS6044304B2 (en) | 1985-10-02 |
| NL174043C (en) | 1984-04-16 |
| FI55196B (en) | 1979-02-28 |
| AU3302471A (en) | 1973-03-08 |
| GB1352723A (en) | 1974-05-08 |
| NO136712B (en) | 1977-07-18 |
| BE772395A (en) | 1972-03-09 |
| OA03911A (en) | 1975-08-14 |
| PL81813B1 (en) | 1975-08-30 |
| SE367203B (en) | 1974-05-20 |
| AU461109B2 (en) | 1975-05-15 |
| PH11935A (en) | 1978-09-15 |
| JPS5390258A (en) | 1978-08-08 |
| YU34689B (en) | 1979-12-31 |
| YU227971A (en) | 1979-07-10 |
| DE2145203A1 (en) | 1972-03-16 |
| JPS544953B1 (en) | 1979-03-12 |
| SU455542A3 (en) | 1974-12-30 |
| IL37633A (en) | 1975-08-31 |
| IL37633A0 (en) | 1971-11-29 |
| NO136712C (en) | 1977-10-26 |
| FR2106434B1 (en) | 1974-10-18 |
| LU63887A1 (en) | 1972-03-01 |
| AT311964B (en) | 1973-12-10 |
| FI55196C (en) | 1979-06-11 |
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