DE3042091A1 - 2-xanthonoxy-2-methylpropionsaeuren, ihre ester und salze, ein verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel - Google Patents
2-xanthonoxy-2-methylpropionsaeuren, ihre ester und salze, ein verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittelInfo
- Publication number
- DE3042091A1 DE3042091A1 DE19803042091 DE3042091A DE3042091A1 DE 3042091 A1 DE3042091 A1 DE 3042091A1 DE 19803042091 DE19803042091 DE 19803042091 DE 3042091 A DE3042091 A DE 3042091A DE 3042091 A1 DE3042091 A1 DE 3042091A1
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen
- formula
- acid
- group
- pharmaceutically acceptable
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 15
- 150000002148 esters Chemical class 0.000 title claims description 6
- 239000008177 pharmaceutical agent Substances 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 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
- 239000002253 acid Substances 0.000 claims description 10
- 239000000460 chlorine Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000001768 cations Chemical class 0.000 claims description 7
- 150000007964 xanthones Chemical class 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 230000001315 anti-hyperlipaemic effect Effects 0.000 claims description 5
- 239000003524 antilipemic agent Substances 0.000 claims description 5
- 229910052801 chlorine Chemical group 0.000 claims description 5
- 229910052736 halogen Chemical group 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- BNLRKUSVMCIOGU-UHFFFAOYSA-N 1-hydroxyxanthen-9-one Chemical compound O1C2=CC=CC=C2C(=O)C2=C1C=CC=C2O BNLRKUSVMCIOGU-UHFFFAOYSA-N 0.000 claims description 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 239000003529 anticholesteremic agent Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 4
- 229960001214 clofibrate Drugs 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000002585 base 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
- 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
- PJJZKNMVBQLGFR-UHFFFAOYSA-N 2-chloro-7-hydroxyxanthen-9-one Chemical compound ClC1=CC=C2OC=3C=CC(=CC3C(C2=C1)=O)O PJJZKNMVBQLGFR-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 102000007330 LDL Lipoproteins Human genes 0.000 description 1
- 108010007622 LDL Lipoproteins Proteins 0.000 description 1
- 102000004895 Lipoproteins Human genes 0.000 description 1
- 108090001030 Lipoproteins Proteins 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 210000001789 adipocyte Anatomy 0.000 description 1
- 239000003513 alkali Substances 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
- 229960002887 deanol Drugs 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
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 239000007787 solid Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 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 (1)
| Publication Number | Publication Date |
|---|---|
| DE3042091A1 true DE3042091A1 (de) | 1981-06-19 |
Family
ID=11250176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803042091 Withdrawn DE3042091A1 (de) | 1979-12-12 | 1980-11-07 | 2-xanthonoxy-2-methylpropionsaeuren, ihre ester und salze, ein verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel |
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 |
Family Cites Families (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 |
| US3655470A (en) * | 1969-03-29 | 1972-04-11 | Toa Gosei Chem Ind | Process for the production of a foamed thermoplastic resin sheet |
| GB1327536A (en) * | 1972-04-13 | 1973-08-22 | Yoshitomi Pharmaceutical | Xanthen-2-yl-propionic acids |
-
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
Also Published As
| Publication number | Publication date |
|---|---|
| IT7941020A0 (it) | 1979-12-12 |
| IT1166191B (it) | 1987-04-29 |
| FR2471379A1 (fr) | 1981-06-19 |
| 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 |
|---|---|---|---|
| 8141 | Disposal/no request for examination |