GB969813A - Improvements in or relating to 1,2,4-oxadiazole derivatives - Google Patents
Improvements in or relating to 1,2,4-oxadiazole derivativesInfo
- Publication number
- GB969813A GB969813A GB2430562A GB2430562A GB969813A GB 969813 A GB969813 A GB 969813A GB 2430562 A GB2430562 A GB 2430562A GB 2430562 A GB2430562 A GB 2430562A GB 969813 A GB969813 A GB 969813A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- general formula
- amidoxime
- hcl
- reacting
- 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
- 150000005071 1,2,4-oxadiazoles Chemical class 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 abstract 1
- 150000001860 citric acid derivatives Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 150000003840 hydrochlorides Chemical class 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- -1 sulphonamido Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
- C07C259/14—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
- C07C259/18—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to carbon atoms of six-membered aromatic rings
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)
Abstract
1,2,4-Oxadiazoles of the general Formula I <FORM:0969813/C1/1> wherein R is acyl, optionally substituted by halogen, alkoxy, alkyl, sulphonamido, or an alkyl substituted or unsubstituted aralkyl including naphthyl, R1 is alkyl, R2 is alkyl, R1 and R1 being identical or different, or R1 and R2 together with the nitrogen atom forming a heterocyclic ring, are made by reacting an amidoxime of the general Formula II <FORM:0969813/C1/2> with acrylyl chloride, in the presence of an HCl capturing agent at ambient or below ambient temperature, and reacting the resulting O-acrylyl-amidoxime with an amine of the general Formula III <FORM:0969813/C1/3> at preferably 40-100 DEG C. The HCl capturing agents specified include alkali-metal carbonates and e.g. pyridine and it is advantageous to perform one or both stages of the reaction in an inert solvent e.g. benzene, chloroform, dioxan and acetone. The products may be converted to their salts, citrates and hydrochlorides being exemplified. Numerous examples are given. Reference has been directed by the Comptroller to Specification 924,608.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT580562 | 1962-03-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB969813A true GB969813A (en) | 1964-09-16 |
Family
ID=11120525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2430562A Expired GB969813A (en) | 1962-03-26 | 1962-06-25 | Improvements in or relating to 1,2,4-oxadiazole derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB969813A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102333764A (en) * | 2009-02-25 | 2012-01-25 | 爱思开生物制药株式会社 | Substituted azole derivatives, pharmaceutical composition containing the derivatives, and method for treating parkinson's disease using the same |
-
1962
- 1962-06-25 GB GB2430562A patent/GB969813A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102333764A (en) * | 2009-02-25 | 2012-01-25 | 爱思开生物制药株式会社 | Substituted azole derivatives, pharmaceutical composition containing the derivatives, and method for treating parkinson's disease using the same |
| EP2401263A4 (en) * | 2009-02-25 | 2012-11-28 | Sk Biopharmaceuticals Co Ltd | SUBSTITUTED AZOLE DERIVATIVES, PHARMACEUTICAL COMPOSITION CONTAINING THE DERIVATIVES, AND METHOD OF TREATING PARKINSON'S DISEASE USING THE SAME |
| US8828992B2 (en) | 2009-02-25 | 2014-09-09 | Sk Biopharmaceuticals Co., Ltd. | Substituted azole derivatives, pharmaceutical composition containing the derivatives, and method for treating Parkinson's disease using the same |
| AU2010218584B2 (en) * | 2009-02-25 | 2015-12-03 | Sk Biopharmaceuticals Co., Ltd. | Substituted azole derivatives, pharmaceutical composition containing the derivatives, and method for treating Parkinson's disease using the same |
| CN102333764B (en) * | 2009-02-25 | 2016-01-06 | 爱思开生物制药株式会社 | The pyrrole derivative replaced, containing the medicinal compositions of these derivatives and treat parkinsonian method with it |
| RU2578596C2 (en) * | 2009-02-25 | 2016-03-27 | Ск Байофармасьютикалз Ко., Лтд. | Substituted azol derivatives, pharmaceutical composition containing these derivatives, and methods of treating parkinson's disease with using these derivatives |
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