JPS5922711B2 - ベンゾオキサゾリノン誘導体の製造法 - Google Patents
ベンゾオキサゾリノン誘導体の製造法Info
- Publication number
- JPS5922711B2 JPS5922711B2 JP49073743A JP7374374A JPS5922711B2 JP S5922711 B2 JPS5922711 B2 JP S5922711B2 JP 49073743 A JP49073743 A JP 49073743A JP 7374374 A JP7374374 A JP 7374374A JP S5922711 B2 JPS5922711 B2 JP S5922711B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- general formula
- producing
- benzoxazolinone
- 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
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical class C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
- 229930182837 (R)-adrenaline Natural products 0.000 description 1
- QXBNAXVXLAHDTE-UHFFFAOYSA-N 6-acetyl-3h-1,3-benzoxazol-2-one Chemical compound CC(=O)C1=CC=C2NC(=O)OC2=C1 QXBNAXVXLAHDTE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000039 congener Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960005139 epinephrine Drugs 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 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
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (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)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7323280A FR2244506B1 (enrdf_load_stackoverflow) | 1973-06-26 | 1973-06-26 | |
| FR7323280 | 1973-06-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5069073A JPS5069073A (enrdf_load_stackoverflow) | 1975-06-09 |
| JPS5922711B2 true JPS5922711B2 (ja) | 1984-05-28 |
Family
ID=9121568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP49073743A Expired JPS5922711B2 (ja) | 1973-06-26 | 1974-06-26 | ベンゾオキサゾリノン誘導体の製造法 |
Country Status (13)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3039929A1 (de) * | 1980-10-23 | 1982-06-03 | Bayer Ag, 5090 Leverkusen | Isocyanato-oxazolinone, ein verfahren zur herstellung von oxazolin-2-on-ringe aufweisenden kunststoffvorlaeufern und deren verwendung zur herstellung von hochmolekularen kunststoffen |
| DE3042481A1 (de) * | 1980-11-11 | 1982-06-16 | A. Nattermann & Cie GmbH, 5000 Köln | (omega)-(2-oxo-benzazolinyl)-alkansaeure-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| GB8325370D0 (en) * | 1983-09-22 | 1983-10-26 | Fujisawa Pharmaceutical Co | Benzoxazoline and benzothiazoline derivatives |
| FR2645149A1 (enrdf_load_stackoverflow) * | 1989-03-30 | 1990-10-05 | Adir | |
| FR2646350B1 (fr) * | 1989-04-28 | 1991-06-28 | Adir | Nouveaux derives benzothiazolinoniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US5166353A (en) * | 1989-04-28 | 1992-11-24 | Adir Et Compagnie | Benzothiazolinone compounds |
| FR2663633B1 (fr) * | 1990-06-22 | 1994-06-17 | Adir | Nouvelles chalcones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2663634B1 (fr) * | 1990-06-22 | 1992-09-04 | Adir | Nouvelles acyl benzoxazolinones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2756825B1 (fr) * | 1996-12-10 | 1999-01-08 | Adir | Nouveaux derives [3h]-benzoxazole-2-thiones et [3h]- benzothiazole-2-thiones substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| JP2002518381A (ja) | 1998-06-18 | 2002-06-25 | ノバルテイス・アクチエンゲゼルシヤフト | ベンザゾール化合物およびその使用 |
| US20120040974A1 (en) * | 2008-08-18 | 2012-02-16 | Yale University | Mif modulators |
| US9643922B2 (en) | 2008-08-18 | 2017-05-09 | Yale University | MIF modulators |
| US9540322B2 (en) | 2008-08-18 | 2017-01-10 | Yale University | MIF modulators |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3050526A (en) * | 1960-08-08 | 1962-08-21 | Rohm & Haas | 3-thiocyanomethyl-2-benzothiazolinones and benzoxazolinones |
-
1973
- 1973-06-26 FR FR7323280A patent/FR2244506B1/fr not_active Expired
-
1974
- 1974-06-20 DE DE2429562A patent/DE2429562A1/de not_active Withdrawn
- 1974-06-24 NL NLAANVRAGE7408489,A patent/NL179135C/xx not_active IP Right Cessation
- 1974-06-24 SE SE7408255A patent/SE424865B/xx not_active IP Right Cessation
- 1974-06-24 GB GB2795274A patent/GB1425429A/en not_active Expired
- 1974-06-25 BE BE145848A patent/BE816820A/xx not_active IP Right Cessation
- 1974-06-25 CH CH180477A patent/CH602679A5/xx not_active IP Right Cessation
- 1974-06-25 IL IL45113A patent/IL45113A/en unknown
- 1974-06-25 LU LU70403A patent/LU70403A1/xx unknown
- 1974-06-25 NO NO742310A patent/NO143531C/no unknown
- 1974-06-25 CH CH372074A patent/CH592642A5/xx not_active IP Right Cessation
- 1974-06-25 DK DK341274A patent/DK341274A/da not_active Application Discontinuation
- 1974-06-25 CA CA203,335A patent/CA1019749A/en not_active Expired
- 1974-06-26 JP JP49073743A patent/JPS5922711B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE7408255L (enrdf_load_stackoverflow) | 1974-12-27 |
| FR2244506A1 (enrdf_load_stackoverflow) | 1975-04-18 |
| DE2429562A1 (de) | 1975-01-16 |
| NL7408489A (enrdf_load_stackoverflow) | 1974-12-30 |
| NO742310L (enrdf_load_stackoverflow) | 1975-01-20 |
| BE816820A (fr) | 1974-12-27 |
| NL179135B (nl) | 1986-02-17 |
| CH602679A5 (enrdf_load_stackoverflow) | 1978-07-31 |
| JPS5069073A (enrdf_load_stackoverflow) | 1975-06-09 |
| SE424865B (sv) | 1982-08-16 |
| CH592642A5 (enrdf_load_stackoverflow) | 1977-10-31 |
| IL45113A (en) | 1977-06-30 |
| DK341274A (enrdf_load_stackoverflow) | 1975-02-24 |
| FR2244506B1 (enrdf_load_stackoverflow) | 1977-02-25 |
| NO143531B (no) | 1980-11-24 |
| IL45113A0 (en) | 1974-09-10 |
| CA1019749A (en) | 1977-10-25 |
| LU70403A1 (enrdf_load_stackoverflow) | 1975-03-27 |
| NL179135C (nl) | 1986-07-16 |
| GB1425429A (en) | 1976-02-18 |
| NO143531C (no) | 1981-03-11 |
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