IE35599L - 2-phenylbenzoxazoles. - Google Patents
2-phenylbenzoxazoles.Info
- Publication number
- IE35599L IE35599L IE711136A IE113671A IE35599L IE 35599 L IE35599 L IE 35599L IE 711136 A IE711136 A IE 711136A IE 113671 A IE113671 A IE 113671A IE 35599 L IE35599 L IE 35599L
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- compounds
- hydrogen
- prepared
- phenyl
- Prior art date
Links
- FIISKTXZUZBTRC-UHFFFAOYSA-N 2-phenyl-1,3-benzoxazole Chemical class C1=CC=CC=C1C1=NC2=CC=CC=C2O1 FIISKTXZUZBTRC-UHFFFAOYSA-N 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 10
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- -1 nitro, amino Chemical group 0.000 abstract 4
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 abstract 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000004970 halomethyl group Chemical group 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 2
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- 125000004953 trihalomethyl group Chemical group 0.000 abstract 2
- BXKPYGNKDSFBHN-UHFFFAOYSA-N 4-(3-amino-3-oxoprop-1-en-2-yl)benzoyl chloride Chemical compound NC(=O)C(=C)C1=CC=C(C(Cl)=O)C=C1 BXKPYGNKDSFBHN-UHFFFAOYSA-N 0.000 abstract 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 206010061218 Inflammation Diseases 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000001118 alkylidene group Chemical group 0.000 abstract 1
- 230000002862 amidating effect Effects 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 230000001760 anti-analgesic effect Effects 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- 239000002221 antipyretic Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000003682 fluorination reaction Methods 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000004054 inflammatory process Effects 0.000 abstract 1
- 150000002690 malonic acid derivatives Chemical class 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 150000002923 oximes Chemical class 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 230000008707 rearrangement Effects 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000003396 thiol group Chemical class [H]S* 0.000 abstract 1
- 125000004385 trihaloalkyl group Chemical group 0.000 abstract 1
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 true IE35599L (en) | 1972-03-10 |
| IE35599B1 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 (8)
| 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 |
| 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 refrigerator |
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 OA OA54349A patent/OA03911A/en unknown
- 1971-09-02 AU AU33024/71A patent/AU461109B2/en not_active Expired
- 1971-09-03 CH CH1295571A patent/CH572916A5/xx not_active IP Right Cessation
- 1971-09-06 AT AT773871A patent/AT311964B/en 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
- 1971-09-07 YU YU2279/71A patent/YU34689B/en unknown
- 1971-09-07 IE IE1136/71A patent/IE35599B1/en unknown
- 1971-09-08 EG EG396/71*UA patent/EG10421A/en active
- 1971-09-08 PL PL1971150397A patent/PL81813B1/en unknown
- 1971-09-09 NO NO3355/71A patent/NO136712C/en unknown
- 1971-09-09 DE DE2145203A patent/DE2145203C2/en not_active Expired
- 1971-09-09 SU SU1696052A patent/SU455542A3/en active
- 1971-09-09 DD DD157648A patent/DD94814A5/xx unknown
- 1971-09-09 SE SE11441/71A patent/SE367203B/xx unknown
- 1971-09-09 LU LU63887D patent/LU63887A1/xx unknown
- 1971-09-09 FI FI2524/71A patent/FI55196C/en active
- 1971-09-09 NL NLAANVRAGE7112437,A patent/NL174043C/en not_active IP Right Cessation
- 1971-09-09 BE BE772395A patent/BE772395A/en not_active IP Right Cessation
- 1971-09-10 FR FR7132748A patent/FR2106434B1/fr not_active Expired
- 1971-09-10 JP JP6981371A patent/JPS544953B1/ja active Pending
- 1971-09-10 RO RO68180A patent/RO61539A/ro unknown
-
1977
- 1977-11-02 JP JP52130931A patent/JPS6044304B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE367203B (en) | 1974-05-20 |
| DD94814A5 (en) | 1973-01-05 |
| NL7112437A (en) | 1972-03-14 |
| FR2106434B1 (en) | 1974-10-18 |
| AU461109B2 (en) | 1975-05-15 |
| NO136712B (en) | 1977-07-18 |
| LU63887A1 (en) | 1972-03-01 |
| NO136712C (en) | 1977-10-26 |
| RO61539A (en) | 1976-12-15 |
| PL81813B1 (en) | 1975-08-30 |
| NL174043C (en) | 1984-04-16 |
| AU3302471A (en) | 1973-03-08 |
| DE2145203A1 (en) | 1972-03-16 |
| IL37633A (en) | 1975-08-31 |
| FI55196C (en) | 1979-06-11 |
| BE772395A (en) | 1972-03-09 |
| CH572916A5 (en) | 1976-02-27 |
| YU227971A (en) | 1979-07-10 |
| FR2106434A1 (en) | 1972-05-05 |
| OA03911A (en) | 1975-08-14 |
| EG10421A (en) | 1976-02-29 |
| NL174043B (en) | 1983-11-16 |
| GB1352723A (en) | 1974-05-08 |
| FI55196B (en) | 1979-02-28 |
| JPS6044304B2 (en) | 1985-10-02 |
| IE35599B1 (en) | 1976-03-31 |
| PH11935A (en) | 1978-09-15 |
| DE2145203C2 (en) | 1984-07-12 |
| IL37633A0 (en) | 1971-11-29 |
| AT311964B (en) | 1973-12-10 |
| JPS5390258A (en) | 1978-08-08 |
| YU34689B (en) | 1979-12-31 |
| JPS544953B1 (en) | 1979-03-12 |
| SU455542A3 (en) | 1974-12-30 |
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