DE2260138A1 - Stoffwechselwirksame bisphenolalkanderivate - Google Patents
Stoffwechselwirksame bisphenolalkanderivateInfo
- Publication number
- DE2260138A1 DE2260138A1 DE2260138A DE2260138A DE2260138A1 DE 2260138 A1 DE2260138 A1 DE 2260138A1 DE 2260138 A DE2260138 A DE 2260138A DE 2260138 A DE2260138 A DE 2260138A DE 2260138 A1 DE2260138 A1 DE 2260138A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- serum
- tert
- alkyl
- hydrogen
- 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- Withdrawn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
- 229930185605 Bisphenol Natural products 0.000 title claims description 5
- 230000004060 metabolic process Effects 0.000 title description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- -1 bisphenol alkane Chemical class 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 230000000055 hyoplipidemic effect Effects 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000002503 metabolic effect Effects 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000000749 insecticidal effect Effects 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 36
- 210000002966 serum Anatomy 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 21
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- 241000700159 Rattus Species 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
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- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
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- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- KUNNUNBSGQSGDY-UHFFFAOYSA-N 2-butyl-6-methylphenol Chemical compound CCCCC1=CC=CC(C)=C1O KUNNUNBSGQSGDY-UHFFFAOYSA-N 0.000 description 2
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 2
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- 229920002261 Corn starch Polymers 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
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- 208000031226 Hyperlipidaemia Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000003472 antidiabetic agent Substances 0.000 description 2
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- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- NRZWYNLTFLDQQX-UHFFFAOYSA-N p-tert-Amylphenol Chemical compound CCC(C)(C)C1=CC=C(O)C=C1 NRZWYNLTFLDQQX-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 210000003800 pharynx Anatomy 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229960001989 prenylamine Drugs 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012261 resinous substance Substances 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- NRHMKIHPTBHXPF-TUJRSCDTSA-M sodium cholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 NRHMKIHPTBHXPF-TUJRSCDTSA-M 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
- C07C39/16—Bis-(hydroxyphenyl) alkanes; Tris-(hydroxyphenyl)alkanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/24—Halogenated derivatives
- C07C39/367—Halogenated derivatives polycyclic non-condensed, containing only six-membered aromatic rings as cyclic parts, e.g. halogenated poly-hydroxyphenylalkanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2260138A DE2260138A1 (de) | 1972-12-08 | 1972-12-08 | Stoffwechselwirksame bisphenolalkanderivate |
| NL7316519A NL7316519A (enrdf_load_stackoverflow) | 1972-12-08 | 1973-12-03 | |
| CA187,455A CA1021353A (en) | 1972-12-08 | 1973-12-05 | Metabolically active bisphenol-alkane derivatives |
| CH1708373A CH611865A5 (en) | 1972-12-08 | 1973-12-05 | Process for the preparation of bisphenolalkane derivatives which are intended for the preparation of medicaments having an effect on the metabolism |
| AU63279/73A AU489219B2 (en) | 1973-12-06 | Metabolically active bisphenol-alkane derivatives | |
| IL43766A IL43766A0 (en) | 1972-12-08 | 1973-12-06 | Pharmaceutical compositions containing bis-phenolalkane derivatives |
| ZA739326A ZA739326B (en) | 1972-12-08 | 1973-12-07 | Metabolically active bisphenol-alkane derivatives |
| JP48137284A JPS4987650A (enrdf_load_stackoverflow) | 1972-12-08 | 1973-12-08 | |
| GB5708973A GB1459420A (en) | 1972-12-08 | 1973-12-10 | Pharmaceutical preparations having hypolipemic and hypoglycemic activity |
| BE138700A BE808441A (fr) | 1972-12-08 | 1973-12-10 | Medicaments a base de derives de bisphenol-alcanes |
| FR7343969A FR2209580B1 (enrdf_load_stackoverflow) | 1972-12-08 | 1973-12-10 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2260138A DE2260138A1 (de) | 1972-12-08 | 1972-12-08 | Stoffwechselwirksame bisphenolalkanderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2260138A1 true DE2260138A1 (de) | 1974-06-12 |
Family
ID=5863903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2260138A Withdrawn DE2260138A1 (de) | 1972-12-08 | 1972-12-08 | Stoffwechselwirksame bisphenolalkanderivate |
Country Status (10)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0112588A3 (en) * | 1982-12-28 | 1986-03-12 | Richter Gedeon Vegyeszeti Gyar R.T. | 4-hydroxy-alpha-ethyl benzhydroles, process for their preparation and medicines containing these compounds |
| EP0112587A3 (en) * | 1982-12-28 | 1986-03-12 | Richter Gedeon Vegyeszeti Gyar R.T. | Derivatives of 4-(1-(phenyl)-1-(hydroxy)-prop-1-yl)-resorcine, process for their preparation and medicines containing these compounds |
| EP0500323A3 (en) * | 1991-02-18 | 1994-06-01 | Sumitomo Chemical Co | Production of bisphenol monoester |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5640629A (en) * | 1979-09-10 | 1981-04-16 | Yoshitomi Pharmaceut Ind Ltd | Trisphenol hydrate |
| US4467121A (en) * | 1980-12-31 | 1984-08-21 | General Electric Company | Fluorinated diphenols and method for their preparation |
| US4365098A (en) * | 1980-12-31 | 1982-12-21 | General Electric Company | Fluorinated diphenols and method for their preparation |
| US4358624A (en) * | 1980-12-31 | 1982-11-09 | General Electric Company | Fluorinated monophenols and diphenols and method for their preparation |
| FR2580275B1 (fr) * | 1985-04-16 | 1988-11-18 | Nouvel Colette | Perfectionnement a la preparation et applications de bisphenols substitues |
| US5827898A (en) * | 1996-10-07 | 1998-10-27 | Shaman Pharmaceuticals, Inc. | Use of bisphenolic compounds to treat type II diabetes |
| EP1222920A3 (en) * | 1998-01-26 | 2003-03-12 | Mitokor | Mitochondria protecting agents for treating mitochondria associated diseases |
| EP1051165A2 (en) | 1998-01-26 | 2000-11-15 | Mitokor | Mitochondria protecting agents for treating mitochondria associated diseases |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1088455A (en) * | 1963-10-21 | 1967-10-25 | Ethyl Corp | Method and composition for reducing plasma lipid levels |
-
1972
- 1972-12-08 DE DE2260138A patent/DE2260138A1/de not_active Withdrawn
-
1973
- 1973-12-03 NL NL7316519A patent/NL7316519A/xx not_active Application Discontinuation
- 1973-12-05 CH CH1708373A patent/CH611865A5/xx not_active IP Right Cessation
- 1973-12-05 CA CA187,455A patent/CA1021353A/en not_active Expired
- 1973-12-06 IL IL43766A patent/IL43766A0/xx unknown
- 1973-12-07 ZA ZA739326A patent/ZA739326B/xx unknown
- 1973-12-08 JP JP48137284A patent/JPS4987650A/ja active Pending
- 1973-12-10 BE BE138700A patent/BE808441A/xx unknown
- 1973-12-10 FR FR7343969A patent/FR2209580B1/fr not_active Expired
- 1973-12-10 GB GB5708973A patent/GB1459420A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0112588A3 (en) * | 1982-12-28 | 1986-03-12 | Richter Gedeon Vegyeszeti Gyar R.T. | 4-hydroxy-alpha-ethyl benzhydroles, process for their preparation and medicines containing these compounds |
| EP0112587A3 (en) * | 1982-12-28 | 1986-03-12 | Richter Gedeon Vegyeszeti Gyar R.T. | Derivatives of 4-(1-(phenyl)-1-(hydroxy)-prop-1-yl)-resorcine, process for their preparation and medicines containing these compounds |
| EP0500323A3 (en) * | 1991-02-18 | 1994-06-01 | Sumitomo Chemical Co | Production of bisphenol monoester |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7316519A (enrdf_load_stackoverflow) | 1974-06-11 |
| FR2209580A1 (enrdf_load_stackoverflow) | 1974-07-05 |
| AU6327973A (en) | 1975-06-12 |
| ZA739326B (en) | 1974-10-30 |
| BE808441A (fr) | 1974-06-10 |
| FR2209580B1 (enrdf_load_stackoverflow) | 1977-01-28 |
| CA1021353A (en) | 1977-11-22 |
| IL43766A0 (en) | 1974-03-14 |
| CH611865A5 (en) | 1979-06-29 |
| JPS4987650A (enrdf_load_stackoverflow) | 1974-08-22 |
| GB1459420A (en) | 1976-12-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8130 | Withdrawal |