GB803372A - Hydroxychromone derivatives and methods of preparing the same - Google Patents
Hydroxychromone derivatives and methods of preparing the sameInfo
- Publication number
- GB803372A GB803372A GB33428/56A GB3342856A GB803372A GB 803372 A GB803372 A GB 803372A GB 33428/56 A GB33428/56 A GB 33428/56A GB 3342856 A GB3342856 A GB 3342856A GB 803372 A GB803372 A GB 803372A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- dimethylchromone
- oxyacetate
- oxyacetic acid
- oxyacetic
- 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
- 238000000034 method Methods 0.000 title abstract 2
- OWBBAPRUYLEWRR-UHFFFAOYSA-N 4-hydroxycoumarin Chemical class C1=CC=C2OC(O)=CC(=O)C2=C1 OWBBAPRUYLEWRR-UHFFFAOYSA-N 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 4
- KQLDYIIDXBUUCK-UHFFFAOYSA-N 2,3-dimethylchromen-4-one Chemical compound C1=CC=C2C(=O)C(C)=C(C)OC2=C1 KQLDYIIDXBUUCK-UHFFFAOYSA-N 0.000 abstract 3
- MRRIROLTJVOMDG-UHFFFAOYSA-N 2-(2,3-dimethyl-4-oxochromen-6-yl)oxyacetic acid Chemical compound CC=1OC2=CC=C(C=C2C(C1C)=O)OCC(=O)O MRRIROLTJVOMDG-UHFFFAOYSA-N 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000003840 hydrochlorides Chemical class 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 229910052700 potassium Inorganic materials 0.000 abstract 3
- MONWLEDQFFNFJP-UHFFFAOYSA-N 2-(2-ethyl-3-methyl-4-oxochromen-7-yl)oxyacetic acid Chemical compound C(C)C=1OC2=CC(=CC=C2C(C1C)=O)OCC(=O)O MONWLEDQFFNFJP-UHFFFAOYSA-N 0.000 abstract 2
- YEHGDIWRWAAVCV-UHFFFAOYSA-N 2-(4-oxo-2-phenylchromen-7-yl)oxyacetic acid Chemical compound C=1C(OCC(=O)O)=CC=C(C(C=2)=O)C=1OC=2C1=CC=CC=C1 YEHGDIWRWAAVCV-UHFFFAOYSA-N 0.000 abstract 2
- HPPSRFJVUIQMLG-UHFFFAOYSA-N 2-ethyl-3-methylchromen-4-one Chemical compound C(C)C=1OC2=CC=CC=C2C(C=1C)=O HPPSRFJVUIQMLG-UHFFFAOYSA-N 0.000 abstract 2
- WVJCRTSTRGRJJT-UHFFFAOYSA-N 7-Hydroxy-4-chromone Chemical compound O1C=CC(=O)C=2C1=CC(O)=CC=2 WVJCRTSTRGRJJT-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 229930003944 flavone Natural products 0.000 abstract 2
- 150000002212 flavone derivatives Chemical class 0.000 abstract 2
- 235000011949 flavones Nutrition 0.000 abstract 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- 239000011591 potassium Substances 0.000 abstract 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 abstract 2
- MAUMSNABMVEOGP-UHFFFAOYSA-N (methyl-$l^{2}-azanyl)methane Chemical compound C[N]C MAUMSNABMVEOGP-UHFFFAOYSA-N 0.000 abstract 1
- ZJWDEMJHVZBLFG-UHFFFAOYSA-N 1,2-dichloro-n,n-diethylethanamine Chemical compound CCN(CC)C(Cl)CCl ZJWDEMJHVZBLFG-UHFFFAOYSA-N 0.000 abstract 1
- DBCOTAKGWCFEPX-UHFFFAOYSA-N 1,2-dichloro-n,n-diethylethanamine;hydrochloride Chemical compound Cl.CCN(CC)C(Cl)CCl DBCOTAKGWCFEPX-UHFFFAOYSA-N 0.000 abstract 1
- JRPNCILONFCLQX-UHFFFAOYSA-N 1,2-dichloro-n,n-dimethylethanamine Chemical compound CN(C)C(Cl)CCl JRPNCILONFCLQX-UHFFFAOYSA-N 0.000 abstract 1
- IFXYCSAMHUFWPU-UHFFFAOYSA-N 2-(2,3-dimethyl-4-oxochromen-7-yl)oxyacetic acid Chemical compound CC=1OC2=CC(=CC=C2C(C1C)=O)OCC(=O)O IFXYCSAMHUFWPU-UHFFFAOYSA-N 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- PXGVCGWYONIOHR-UHFFFAOYSA-N 6-hydroxy-2,3-dimethylchromen-4-one Chemical compound OC=1C=C2C(C(=C(OC2=CC1)C)C)=O PXGVCGWYONIOHR-UHFFFAOYSA-N 0.000 abstract 1
- CJIJXIFQYOPWTF-UHFFFAOYSA-N 7-hydroxycoumarin Natural products O1C(=O)C=CC2=CC(O)=CC=C21 CJIJXIFQYOPWTF-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- -1 alkali metal salt Chemical class 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 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
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
The invention comprises compounds having a coronaro-dilating action of the general formula <FORM:0803372/IV (b)/1> wherein (a) R and R1 are both methyl groups, the chain R2OOC.CH2O- is indifferently in position 6 or 7, and R2 is H, Na, K, C2H5, (C2H5)2N(HCl).CH2.CH2- or the hydrochloride of the b -piperidino-ethyl radical; (b) R is methyl, R1 is ethyl, the chain R2OOC.CH2O- is in the 7-position and R2 is as in (a) or (CH3)2N(HCl).CH2.CH2-; or (c) R is H and R1 is phenyl, the chain R2OOC.CH2O- is in the 7-position and R2 is as in (b), or another alkyl group of from one to six carbon atoms; and a process for their preparation by boiling in solution or suspension a substituted 6- or 7-hydroxychromone with an alkyl halogen acetate, in which the alkyl group has from one to six carbon atoms, in the presence of an alkali metal carbonate for between seven and twelve hours. The oxyacetic ester is then recovered from the mixture and, if required, subjected to alkaline alcoholic hydrolysis at 40 DEG C. to yield the corresponding alkali metal salt, which may then be acidified to give the free acid, or boiled with the hydrochlorides of b -dimethylaminoethyl chloride, b -diethylaminoethyl chloride or b -piperidinoethyl chloride in isopropanol for from four to five hours to yield the corresponding amino-esters. The free acids may also be obtained direct by acid hydrolysis of the original oxyacetic esters. In examples: (1) 6-hydroxy-2,3 - dimethylchromone, ethyl bromoacetate, and potassium carbonate are refluxed in acetone, yielding 2,3 - dimethyl - chromone 6 - ethyl oxyacetate; similarly (2) to (15) are prepared following: 2,3 - dimethylchromone - 7 - ethyl oxyacetate, 2 - ethyl - 3 - methylchromone - 7 - ethyl oxyacetate and the methyl, ethyl, n-propyl, isopropyl, allyl, secbutyl, isobutyl, butyl, amyl, isoamyl, inactive amyl, and hexyl esters of flavone-7-oxyacetic acid; (16) 2,3-dimethylchromone-6-ethyl oxyacetate in ethanol is treated with ethanolic KOH when the potassium salt of 2,3-dimethylchromone-6-oxyacetic acid separates; likewise (17) to (19), are prepared 2,3-dimethylchromone-7-potassium oxyacetate, 2 - ethyl - 3 - methylchromone - 7 - potassium oxyacetate and flavone - 7 - sodium oxyacetate; (20) 2,3-dimethylchromone-6-ethyl oxyacetate is refluxed with 70 per cent H2SO4, giving 2,3-dimethylchromone-6-oxyacetic acid; (21) to (23), as in (20) are prepared 2,3-dimethylchromone - 7 - oxyacetic acid, 2 - ethyl - 3 - methylchromone-7-oxyacetic acid and flavone-7-oxyacetic acid; (24) the potassium salt of 2,3-dimethylchromone-6-oxyacetic acid is reacted with b - diethylaminoethyl chloride hydrochloride in isopropanol giving 2,3-dimethylchromone - 6 - b - diethylaminoethyl oxyacetate hydrochloride; likewise (25) to (33) are prepared the b -piperidinoethyl and b -diethylaminoethyl esters of 2,3-dimethylchromone-6- and 7-oxyacetic acids, of 2-ethyl-3-methylchromone-7-oxyacetic acid and of flavone 7-oxyacetic acid in the form of their hydrochlorides, and also the b -diethylaminoethyl esters of the two last-mentioned acids, again as their hydrochloride salts.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT803372X | 1955-11-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB803372A true GB803372A (en) | 1958-10-22 |
Family
ID=11316923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB33428/56A Expired GB803372A (en) | 1955-11-02 | 1956-11-01 | Hydroxychromone derivatives and methods of preparing the same |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB803372A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1193511B (en) * | 1961-03-16 | 1965-05-26 | Cassella Farbwerke Mainkur Ag | Process for the preparation of derivatives of 7-oxychromone |
| DE1210882B (en) * | 1961-07-14 | 1966-02-17 | Cassella Farbwerke Mainkur Ag | Process for the preparation of derivatives of 7-oxychromone |
| DE1290150B (en) * | 1960-08-04 | 1969-03-06 | Blaise Rolland | Process for the production of the disodium salt of flavone-5, 7-di- (oxyacetic acid) |
| EP0248420A3 (en) * | 1986-06-04 | 1988-10-12 | Daiichi Seiyaku Co. Ltd. | Benzopyran derivatives |
| WO2004017964A1 (en) | 2002-08-19 | 2004-03-04 | Pfizer Products Inc. | Combination therapy for hyperproliferative diseases |
| WO2007062314A2 (en) | 2005-11-23 | 2007-05-31 | Bristol-Myers Squibb Company | Heterocyclic cetp inhibitors |
| WO2008070496A2 (en) | 2006-12-01 | 2008-06-12 | Bristol-Myers Squibb Company | N- ( (3-benzyl) -2, 2- (bis-phenyl) -propan-1-amine derivatives as cetp inhibitors for the treatment of atherosclerosis and cardiovascular diseases |
| EP2392567A1 (en) | 2005-10-21 | 2011-12-07 | Bristol-Myers Squibb Company | Benzothiazine derivatives and their use as lxr modulators |
| WO2014170786A1 (en) | 2013-04-17 | 2014-10-23 | Pfizer Inc. | N-piperidin-3-ylbenzamide derivatives for treating cardiovascular diseases |
| WO2016055901A1 (en) | 2014-10-08 | 2016-04-14 | Pfizer Inc. | Substituted amide compounds |
| WO2020150473A2 (en) | 2019-01-18 | 2020-07-23 | Dogma Therapeutics, Inc. | Pcsk9 inhibitors and methods of use thereof |
-
1956
- 1956-11-01 GB GB33428/56A patent/GB803372A/en not_active Expired
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1290150B (en) * | 1960-08-04 | 1969-03-06 | Blaise Rolland | Process for the production of the disodium salt of flavone-5, 7-di- (oxyacetic acid) |
| DE1193511B (en) * | 1961-03-16 | 1965-05-26 | Cassella Farbwerke Mainkur Ag | Process for the preparation of derivatives of 7-oxychromone |
| DE1210882B (en) * | 1961-07-14 | 1966-02-17 | Cassella Farbwerke Mainkur Ag | Process for the preparation of derivatives of 7-oxychromone |
| EP0248420A3 (en) * | 1986-06-04 | 1988-10-12 | Daiichi Seiyaku Co. Ltd. | Benzopyran derivatives |
| US4841076A (en) * | 1986-06-04 | 1989-06-20 | Daiichi Seiyaku Co., Ltd. | Benzopyran derivatives |
| WO2004017964A1 (en) | 2002-08-19 | 2004-03-04 | Pfizer Products Inc. | Combination therapy for hyperproliferative diseases |
| EP2392567A1 (en) | 2005-10-21 | 2011-12-07 | Bristol-Myers Squibb Company | Benzothiazine derivatives and their use as lxr modulators |
| WO2007062314A2 (en) | 2005-11-23 | 2007-05-31 | Bristol-Myers Squibb Company | Heterocyclic cetp inhibitors |
| WO2008070496A2 (en) | 2006-12-01 | 2008-06-12 | Bristol-Myers Squibb Company | N- ( (3-benzyl) -2, 2- (bis-phenyl) -propan-1-amine derivatives as cetp inhibitors for the treatment of atherosclerosis and cardiovascular diseases |
| WO2014170786A1 (en) | 2013-04-17 | 2014-10-23 | Pfizer Inc. | N-piperidin-3-ylbenzamide derivatives for treating cardiovascular diseases |
| WO2016055901A1 (en) | 2014-10-08 | 2016-04-14 | Pfizer Inc. | Substituted amide compounds |
| WO2020150473A2 (en) | 2019-01-18 | 2020-07-23 | Dogma Therapeutics, Inc. | Pcsk9 inhibitors and methods of use thereof |
| EP4470609A2 (en) | 2019-01-18 | 2024-12-04 | Astrazeneca AB | Pcsk9 inhibitors and methods of use thereof |
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