CA1076592A - 4-oxo-4h-1-benzopyran-2-carboxylic acid and derivatives thereof - Google Patents
4-oxo-4h-1-benzopyran-2-carboxylic acid and derivatives thereofInfo
- Publication number
- CA1076592A CA1076592A CA264,396A CA264396A CA1076592A CA 1076592 A CA1076592 A CA 1076592A CA 264396 A CA264396 A CA 264396A CA 1076592 A CA1076592 A CA 1076592A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- hydrogen
- process according
- ester
- 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
- RVMGXWBCQGAWBR-UHFFFAOYSA-N 4-oxo-1-benzopyran-2-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)=CC(=O)C2=C1 RVMGXWBCQGAWBR-UHFFFAOYSA-N 0.000 title claims 2
- 229910052739 hydrogen Chemical group 0.000 claims abstract description 16
- 239000001257 hydrogen Chemical group 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 14
- 150000002148 esters Chemical class 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims abstract description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 4
- -1 2-hydroxytrimethylene Chemical group 0.000 claims description 2
- 241000790917 Dioxys <bee> Species 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- CJTURQGHQPDNDA-UHFFFAOYSA-N 6,8-ditert-butyl-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C21 CJTURQGHQPDNDA-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Chemical group 0.000 claims 1
- 150000001340 alkali metals Chemical group 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 201000009961 allergic asthma Diseases 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 239000001120 potassium sulphate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/24—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4832175 | 1975-11-25 | ||
| GB4832275 | 1975-11-25 | ||
| GB1473276 | 1976-04-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1076592A true CA1076592A (en) | 1980-04-29 |
Family
ID=27257160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA264,396A Expired CA1076592A (en) | 1975-11-25 | 1976-10-28 | 4-oxo-4h-1-benzopyran-2-carboxylic acid and derivatives thereof |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5265273A (cs) |
| CA (1) | CA1076592A (cs) |
| CH (1) | CH618435A5 (cs) |
| DK (1) | DK530076A (cs) |
| ES (1) | ES453593A1 (cs) |
| FI (1) | FI763347A7 (cs) |
| NO (1) | NO146498C (cs) |
| PT (1) | PT65881B (cs) |
| SE (1) | SE425313B (cs) |
-
1976
- 1976-10-28 CA CA264,396A patent/CA1076592A/en not_active Expired
- 1976-11-11 NO NO763856A patent/NO146498C/no unknown
- 1976-11-22 FI FI763347A patent/FI763347A7/fi not_active Application Discontinuation
- 1976-11-24 CH CH1479976A patent/CH618435A5/fr not_active IP Right Cessation
- 1976-11-24 SE SE7613152A patent/SE425313B/xx unknown
- 1976-11-24 DK DK530076A patent/DK530076A/da not_active Application Discontinuation
- 1976-11-24 ES ES453593A patent/ES453593A1/es not_active Expired
- 1976-11-24 PT PT65881A patent/PT65881B/pt unknown
- 1976-11-25 JP JP51140826A patent/JPS5265273A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ES453593A1 (es) | 1977-12-01 |
| JPS5265273A (en) | 1977-05-30 |
| NO146498C (no) | 1982-10-13 |
| SE7613152L (sv) | 1977-05-26 |
| PT65881A (fr) | 1976-12-01 |
| PT65881B (fr) | 1978-10-12 |
| SE425313B (sv) | 1982-09-20 |
| FI763347A7 (cs) | 1977-05-26 |
| NO763856L (cs) | 1977-05-26 |
| CH618435A5 (en) | 1980-07-31 |
| NO146498B (no) | 1982-07-05 |
| DK530076A (da) | 1977-05-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |