FR2471379A1 - Acides 2-xanthonoxy-2-methyl propioniques, leurs esters et leurs sels, leur procede de preparation et leur application en therapeutique - Google Patents
Acides 2-xanthonoxy-2-methyl propioniques, leurs esters et leurs sels, leur procede de preparation et leur application en therapeutique Download PDFInfo
- Publication number
- FR2471379A1 FR2471379A1 FR8025095A FR8025095A FR2471379A1 FR 2471379 A1 FR2471379 A1 FR 2471379A1 FR 8025095 A FR8025095 A FR 8025095A FR 8025095 A FR8025095 A FR 8025095A FR 2471379 A1 FR2471379 A1 FR 2471379A1
- Authority
- FR
- France
- Prior art keywords
- hydrogen
- acid
- xanthonoxy
- hydrogen atom
- formula
- 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.)
- Granted
Links
- 150000003839 salts Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 150000001768 cations Chemical class 0.000 claims abstract description 6
- 230000001315 anti-hyperlipaemic effect Effects 0.000 claims abstract description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 239000003524 antilipemic agent Substances 0.000 claims description 5
- 229910052801 chlorine Chemical group 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- -1 alkyl radical Chemical class 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 229960002887 deanol Drugs 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- BNLRKUSVMCIOGU-UHFFFAOYSA-N 1-hydroxyxanthen-9-one Chemical compound O1C2=CC=CC=C2C(=O)C2=C1C=CC=C2O BNLRKUSVMCIOGU-UHFFFAOYSA-N 0.000 claims 1
- 230000002484 anti-cholesterolemic effect Effects 0.000 claims 1
- 239000003981 vehicle Substances 0.000 claims 1
- 150000007964 xanthones Chemical class 0.000 claims 1
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 abstract description 7
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical group [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 229960001214 clofibrate Drugs 0.000 description 3
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 2
- 229930182837 (R)-adrenaline Natural products 0.000 description 2
- XCJHDJAODLKGLG-UHFFFAOYSA-N 3-hydroxyxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=C(O)C=C3OC2=C1 XCJHDJAODLKGLG-UHFFFAOYSA-N 0.000 description 2
- 206010003210 Arteriosclerosis Diseases 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 102000004895 Lipoproteins Human genes 0.000 description 2
- 108090001030 Lipoproteins Proteins 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229940127226 anticholesterol agent Drugs 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000007071 enzymatic hydrolysis Effects 0.000 description 2
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 2
- 229960005139 epinephrine Drugs 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 230000004130 lipolysis Effects 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 241000700159 Rattus Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000000923 atherogenic effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 201000010063 epididymitis Diseases 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052736 halogen Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000037303 wrinkles Effects 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
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes 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 9
- C07D311/86—Oxygen atoms, e.g. xanthones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT41020/79A IT1166191B (it) | 1979-12-12 | 1979-12-12 | Acidi 2 xantonossi 2 metilpropionici loro esteri e loro sali caratterizzati da attivita ipolipemizzante |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2471379A1 true FR2471379A1 (fr) | 1981-06-19 |
| FR2471379B1 FR2471379B1 (OSRAM) | 1985-01-04 |
Family
ID=11250176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8025095A Granted FR2471379A1 (fr) | 1979-12-12 | 1980-11-26 | Acides 2-xanthonoxy-2-methyl propioniques, leurs esters et leurs sels, leur procede de preparation et leur application en therapeutique |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5692883A (OSRAM) |
| DE (1) | DE3042091A1 (OSRAM) |
| FR (1) | FR2471379A1 (OSRAM) |
| GB (1) | GB2065107B (OSRAM) |
| IT (1) | IT1166191B (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4661607A (en) * | 1984-09-21 | 1987-04-28 | Chugai Seiyaku Kabushiki Kaisha | Furoxanthone derivatives useful as diuretics |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1417961A (fr) * | 1961-01-19 | 1965-11-19 | Cassella Farbwerke Mainkur Ag | Procédé de préparation de dérivés d'hydroxy-xanthones |
| FR2035989A1 (OSRAM) * | 1969-03-29 | 1970-12-24 | Yoshitomi Pharmaceutical | |
| FR2189026A2 (OSRAM) * | 1972-04-13 | 1974-01-25 | Yoshitomi Pharmaceutical |
-
1979
- 1979-12-12 IT IT41020/79A patent/IT1166191B/it active
-
1980
- 1980-11-05 GB GB8035598A patent/GB2065107B/en not_active Expired
- 1980-11-07 DE DE19803042091 patent/DE3042091A1/de not_active Withdrawn
- 1980-11-26 FR FR8025095A patent/FR2471379A1/fr active Granted
- 1980-12-12 JP JP17646880A patent/JPS5692883A/ja active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1417961A (fr) * | 1961-01-19 | 1965-11-19 | Cassella Farbwerke Mainkur Ag | Procédé de préparation de dérivés d'hydroxy-xanthones |
| FR2035989A1 (OSRAM) * | 1969-03-29 | 1970-12-24 | Yoshitomi Pharmaceutical | |
| FR2189026A2 (OSRAM) * | 1972-04-13 | 1974-01-25 | Yoshitomi Pharmaceutical |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3042091A1 (de) | 1981-06-19 |
| IT7941020A0 (it) | 1979-12-12 |
| IT1166191B (it) | 1987-04-29 |
| GB2065107A (en) | 1981-06-24 |
| JPS5692883A (en) | 1981-07-27 |
| FR2471379B1 (OSRAM) | 1985-01-04 |
| GB2065107B (en) | 1983-06-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |