DE2326061C3 - Bis-(halogenphenoxy)-essigsäuretrimethylcyclohexylester, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel - Google Patents
Bis-(halogenphenoxy)-essigsäuretrimethylcyclohexylester, Verfahren zu ihrer Herstellung und diese enthaltende ArzneimittelInfo
- Publication number
- DE2326061C3 DE2326061C3 DE19732326061 DE2326061A DE2326061C3 DE 2326061 C3 DE2326061 C3 DE 2326061C3 DE 19732326061 DE19732326061 DE 19732326061 DE 2326061 A DE2326061 A DE 2326061A DE 2326061 C3 DE2326061 C3 DE 2326061C3
- Authority
- DE
- Germany
- Prior art keywords
- bis
- acetic acid
- trimethylcyclohexyl
- halophenoxy
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title description 20
- -1 Trimethylcyclohexyl Chemical group 0.000 title description 7
- 238000000034 method Methods 0.000 title description 6
- 239000003814 drug Substances 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 3
- AWBWXVGYQIXJKF-UHFFFAOYSA-N (1,2,2-trimethylcyclohexyl) acetate Chemical compound CC(=O)OC1(C)CCCCC1(C)C AWBWXVGYQIXJKF-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 16
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 235000005911 diet Nutrition 0.000 description 8
- 230000037213 diet Effects 0.000 description 8
- 235000012000 cholesterol Nutrition 0.000 description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
- BRRVXFOKWJKTGG-UHFFFAOYSA-N 3,3,5-trimethylcyclohexanol Chemical compound CC1CC(O)CC(C)(C)C1 BRRVXFOKWJKTGG-UHFFFAOYSA-N 0.000 description 6
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 6
- 229960001214 clofibrate Drugs 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- ZKNSZZXBPSICFK-UHFFFAOYSA-N 2,2-bis(4-chlorophenoxy)acetic acid Chemical compound C=1C=C(Cl)C=CC=1OC(C(=O)O)OC1=CC=C(Cl)C=C1 ZKNSZZXBPSICFK-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 230000002402 anti-lipaemic effect Effects 0.000 description 5
- 235000019197 fats Nutrition 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- 241000700159 Rattus Species 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000012024 dehydrating agents Substances 0.000 description 4
- 230000000260 hypercholesteremic effect Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000014121 butter Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- 230000000304 vasodilatating effect Effects 0.000 description 3
- BRRVXFOKWJKTGG-SFYZADRCSA-N (1s,5s)-3,3,5-trimethylcyclohexan-1-ol Chemical compound C[C@@H]1C[C@H](O)CC(C)(C)C1 BRRVXFOKWJKTGG-SFYZADRCSA-N 0.000 description 2
- XBYHGNVNQLXAGB-UHFFFAOYSA-N 2,2-bis(2-chlorophenoxy)acetic acid Chemical compound C=1C=CC=C(Cl)C=1OC(C(=O)O)OC1=CC=CC=C1Cl XBYHGNVNQLXAGB-UHFFFAOYSA-N 0.000 description 2
- OMLRMBITDMLLSE-UHFFFAOYSA-N 2,2-bis(4-fluorophenoxy)acetic acid Chemical compound FC1=CC=C(OC(C(=O)O)OC2=CC=C(C=C2)F)C=C1 OMLRMBITDMLLSE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- BRRVXFOKWJKTGG-YUMQZZPRSA-N (1s,5r)-3,3,5-trimethylcyclohexan-1-ol Chemical compound C[C@H]1C[C@H](O)CC(C)(C)C1 BRRVXFOKWJKTGG-YUMQZZPRSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- DJDVLUMEEFHDEA-UHFFFAOYSA-N 2,2-bis[3-(trifluoromethyl)phenoxy]acetic acid Chemical compound FC(C=1C=C(OC(C(=O)O)OC2=CC(=CC=C2)C(F)(F)F)C=CC1)(F)F DJDVLUMEEFHDEA-UHFFFAOYSA-N 0.000 description 1
- 206010014476 Elevated cholesterol Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 208000035150 Hypercholesterolemia Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000002484 anti-cholesterolemic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- VXPXCNZMCSKVAS-UHFFFAOYSA-N cyclohexyl 2,2-bis(4-chlorophenoxy)acetate Chemical compound C1=CC(Cl)=CC=C1OC(C(=O)OC1CCCCC1)OC1=CC=C(Cl)C=C1 VXPXCNZMCSKVAS-UHFFFAOYSA-N 0.000 description 1
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 231100000171 higher toxicity Toxicity 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
- 230000000055 hyoplipidemic effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732326061 DE2326061C3 (de) | 1973-05-23 | 1973-05-23 | Bis-(halogenphenoxy)-essigsäuretrimethylcyclohexylester, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| FR7417837A FR2230368B1 (https=) | 1973-05-23 | 1974-05-22 | |
| GB2319074A GB1417817A (en) | 1973-05-23 | 1974-05-23 | Substituted acetic acid cyclohexyl esters the preparation thereof and pharmaceutical compositions containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732326061 DE2326061C3 (de) | 1973-05-23 | 1973-05-23 | Bis-(halogenphenoxy)-essigsäuretrimethylcyclohexylester, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2326061A1 DE2326061A1 (de) | 1974-12-05 |
| DE2326061B2 DE2326061B2 (de) | 1975-03-27 |
| DE2326061C3 true DE2326061C3 (de) | 1975-11-13 |
Family
ID=5881776
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732326061 Expired DE2326061C3 (de) | 1973-05-23 | 1973-05-23 | Bis-(halogenphenoxy)-essigsäuretrimethylcyclohexylester, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE2326061C3 (https=) |
| FR (1) | FR2230368B1 (https=) |
| GB (1) | GB1417817A (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4008265A (en) * | 1971-05-22 | 1977-02-15 | Sumitomo Chemical Company, Limited | Novel bisphenoxy carboxylic acid derivatives and their salts |
| DE10332908A1 (de) * | 2003-07-19 | 2005-02-10 | Symrise Gmbh & Co. Kg | cis-3,3,5-Trimethylcyclohexylester |
-
1973
- 1973-05-23 DE DE19732326061 patent/DE2326061C3/de not_active Expired
-
1974
- 1974-05-22 FR FR7417837A patent/FR2230368B1/fr not_active Expired
- 1974-05-23 GB GB2319074A patent/GB1417817A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2230368A1 (https=) | 1974-12-20 |
| DE2326061A1 (de) | 1974-12-05 |
| FR2230368B1 (https=) | 1977-07-08 |
| DE2326061B2 (de) | 1975-03-27 |
| GB1417817A (en) | 1975-12-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |