DE2406849C3 - Nicotinsäure-trans-3,3,5-trimethylcyclohex-1-yl-ester, Verfahren zu seiner Herstellung und diesen Ester enthaltendes Arzneimittel - Google Patents
Nicotinsäure-trans-3,3,5-trimethylcyclohex-1-yl-ester, Verfahren zu seiner Herstellung und diesen Ester enthaltendes ArzneimittelInfo
- Publication number
- DE2406849C3 DE2406849C3 DE2406849A DE2406849A DE2406849C3 DE 2406849 C3 DE2406849 C3 DE 2406849C3 DE 2406849 A DE2406849 A DE 2406849A DE 2406849 A DE2406849 A DE 2406849A DE 2406849 C3 DE2406849 C3 DE 2406849C3
- Authority
- DE
- Germany
- Prior art keywords
- ester
- nicotinic acid
- trans
- trimethyl
- preparation
- 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 claims description 4
- 239000003814 drug Substances 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000002148 esters Chemical class 0.000 title description 19
- GQSGZTBDVNUIQS-AAEUAGOBSA-N [(1s,5r)-3,3,5-trimethylcyclohexyl] pyridine-3-carboxylate Chemical compound C1C(C)(C)C[C@@H](C)C[C@@H]1OC(=O)C1=CC=CN=C1 GQSGZTBDVNUIQS-AAEUAGOBSA-N 0.000 title 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 16
- 229960003512 nicotinic acid Drugs 0.000 claims description 10
- 235000001968 nicotinic acid Nutrition 0.000 claims description 10
- 239000011664 nicotinic acid Substances 0.000 claims description 10
- 230000000055 hyoplipidemic effect Effects 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 3
- MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 230000000304 vasodilatating effect Effects 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000000812 cholinergic antagonist Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 230000002048 spasmolytic effect Effects 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- -1 nicotinic acid ester Chemical class 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 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 6
- 230000000694 effects Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 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 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- 150000003904 phospholipids Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 229960002510 mandelic acid Drugs 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- UENOQWSWMYJKIW-UHFFFAOYSA-N 1,2,2-trimethylcyclohexan-1-ol Chemical compound CC1(C)CCCCC1(C)O UENOQWSWMYJKIW-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 201000005577 familial hyperlipidemia Diseases 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21498/73A IT1060356B (it) | 1973-03-12 | 1973-03-12 | Estere nicotinico e composizione farmaceutica ad azione vasodilata trice spasmolitica e ipolipemizzante e processo per la preparazione di detto estere |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2406849A1 DE2406849A1 (de) | 1974-09-19 |
| DE2406849B2 DE2406849B2 (de) | 1980-06-26 |
| DE2406849C3 true DE2406849C3 (de) | 1981-06-04 |
Family
ID=11182704
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2406849A Expired DE2406849C3 (de) | 1973-03-12 | 1974-02-13 | Nicotinsäure-trans-3,3,5-trimethylcyclohex-1-yl-ester, Verfahren zu seiner Herstellung und diesen Ester enthaltendes Arzneimittel |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE810911A (https=) |
| CH (1) | CH585717A5 (https=) |
| DE (1) | DE2406849C3 (https=) |
| ES (1) | ES421834A1 (https=) |
| FR (1) | FR2221130B1 (https=) |
| GB (1) | GB1409990A (https=) |
| IT (1) | IT1060356B (https=) |
| NL (1) | NL7402866A (https=) |
| ZA (1) | ZA741531B (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10332908A1 (de) * | 2003-07-19 | 2005-02-10 | Symrise Gmbh & Co. Kg | cis-3,3,5-Trimethylcyclohexylester |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE729170A (https=) * | 1968-03-02 | 1969-08-01 |
-
1973
- 1973-03-12 IT IT21498/73A patent/IT1060356B/it active
- 1973-06-19 FR FR7322261A patent/FR2221130B1/fr not_active Expired
- 1973-12-28 ES ES421834A patent/ES421834A1/es not_active Expired
-
1974
- 1974-02-12 BE BE140813A patent/BE810911A/xx not_active IP Right Cessation
- 1974-02-13 DE DE2406849A patent/DE2406849C3/de not_active Expired
- 1974-02-14 CH CH203674A patent/CH585717A5/xx not_active IP Right Cessation
- 1974-03-04 NL NL7402866A patent/NL7402866A/xx unknown
- 1974-03-08 ZA ZA00741531A patent/ZA741531B/xx unknown
- 1974-03-12 GB GB1106074A patent/GB1409990A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT1060356B (it) | 1982-07-10 |
| DE2406849A1 (de) | 1974-09-19 |
| BE810911A (fr) | 1974-05-29 |
| FR2221130B1 (https=) | 1976-07-16 |
| NL7402866A (https=) | 1974-09-16 |
| ES421834A1 (es) | 1976-08-01 |
| CH585717A5 (https=) | 1977-03-15 |
| GB1409990A (en) | 1975-10-15 |
| ZA741531B (en) | 1975-02-26 |
| DE2406849B2 (de) | 1980-06-26 |
| FR2221130A1 (https=) | 1974-10-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |