GB1024645A - Chromone compounds - Google Patents
Chromone compoundsInfo
- Publication number
- GB1024645A GB1024645A GB2640362A GB2640362A GB1024645A GB 1024645 A GB1024645 A GB 1024645A GB 2640362 A GB2640362 A GB 2640362A GB 2640362 A GB2640362 A GB 2640362A GB 1024645 A GB1024645 A GB 1024645A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chroman
- hydroxy
- acid
- contacting
- propionic acid
- 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
- 150000004777 chromones Chemical class 0.000 title 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- NESDMCGUYCOYQH-UHFFFAOYSA-N 1-(6-hydroxy-3,4-dihydro-2h-chromen-7-yl)ethanone Chemical compound O1CCCC2=C1C=C(C(=O)C)C(O)=C2 NESDMCGUYCOYQH-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- 230000000397 acetylating effect Effects 0.000 abstract 2
- 239000003377 acid catalyst Substances 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 2
- 235000019260 propionic acid Nutrition 0.000 abstract 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 abstract 2
- APDIEUFOBVDFBQ-UHFFFAOYSA-N 2-(4-acetyloxyphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(OC(C)=O)C=C1 APDIEUFOBVDFBQ-UHFFFAOYSA-N 0.000 abstract 1
- JRMAQQQTXDJDNC-UHFFFAOYSA-M 2-ethoxy-2-oxoacetate Chemical compound CCOC(=O)C([O-])=O JRMAQQQTXDJDNC-UHFFFAOYSA-M 0.000 abstract 1
- WQIFYZCOEREGBU-UHFFFAOYSA-N 3,4-dihydro-2h-chromen-6-yl acetate Chemical compound O1CCCC2=CC(OC(=O)C)=CC=C21 WQIFYZCOEREGBU-UHFFFAOYSA-N 0.000 abstract 1
- MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical compound C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 abstract 1
- GIKMYBNGVOXIJU-UHFFFAOYSA-N 6-methoxy-3,4-dihydro-2h-chromene Chemical compound O1CCCC2=CC(OC)=CC=C21 GIKMYBNGVOXIJU-UHFFFAOYSA-N 0.000 abstract 1
- BFRVCQPRUJFVFU-UHFFFAOYSA-N 6-methoxy-3,4-dihydrochromen-2-one Chemical compound O1C(=O)CCC2=CC(OC)=CC=C21 BFRVCQPRUJFVFU-UHFFFAOYSA-N 0.000 abstract 1
- 229910015900 BF3 Inorganic materials 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- LVZGQWKTUCVPBQ-UHFFFAOYSA-N acetic acid;trifluoroborane Chemical compound CC(O)=O.FB(F)F LVZGQWKTUCVPBQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000000443 aerosol Substances 0.000 abstract 1
- GZCJJOLJSBCUNR-UHFFFAOYSA-N chroman-6-ol Chemical compound O1CCCC2=CC(O)=CC=C21 GZCJJOLJSBCUNR-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000006071 cream Substances 0.000 abstract 1
- 125000005594 diketone group Chemical group 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- 239000006210 lotion Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000006072 paste Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention comprises 6-oxa-cyclohexano-[g] - chromone - 2 - carboxylic acid, salts and esters thereof and a process for the preparation thereof by condensing 7-acetyl-6-hydroxy-chroman with ethyl oxalate and cyclising the resultant diketone by heating with ethanolic HCl, H2SO4 or boron trifluoride to obtain the ethyl ester, or with glacial acetic acid and HCl to obtain the free acid. The 7-acetyl-6-hydroxy-chroman may be obtained by contacting b -(p-methoxyphenoxy) propionic acid with a strong acid catalyst to yield 6-methoxy-chromanone, reducing the chromanone to 6-methoxy chroman and contacting this with boron trifluoride acetic acid complex, or by acetylating b -(p-hydroxy-phenoxy) propionic acid with acetic anhydride, contacting the resulting (p-acetoxyphenoxy) propionic acid with a strong acid catalyst to yield 6-hydroxy chroman, acetylating to form 6-acetoxy chroman which is contacted with aluminium chloride. Pharmaceutical compositions having activity as inhibitors of the antigen-antibody reaction and containing the above compounds are administered orally in tablets, in solutions for injection or topically as creams, lotions and pastes or in an aerosol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2640362A GB1024645A (en) | 1962-07-10 | 1962-07-10 | Chromone compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2640362A GB1024645A (en) | 1962-07-10 | 1962-07-10 | Chromone compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1024645A true GB1024645A (en) | 1966-03-30 |
Family
ID=10243098
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2640362A Expired GB1024645A (en) | 1962-07-10 | 1962-07-10 | Chromone compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1024645A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4238606A (en) * | 1974-11-30 | 1980-12-09 | Fisons Limited | Tricyclic mono-chromone-2-carboxylic acids |
-
1962
- 1962-07-10 GB GB2640362A patent/GB1024645A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4238606A (en) * | 1974-11-30 | 1980-12-09 | Fisons Limited | Tricyclic mono-chromone-2-carboxylic acids |
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