DE1593147A1 - Cyclohexanole,Verfahren zu ihrer Herstellung und Arzneimittel mit einem Gehalt an diesen Verbindungen - Google Patents
Cyclohexanole,Verfahren zu ihrer Herstellung und Arzneimittel mit einem Gehalt an diesen VerbindungenInfo
- Publication number
- DE1593147A1 DE1593147A1 DE19661593147 DE1593147A DE1593147A1 DE 1593147 A1 DE1593147 A1 DE 1593147A1 DE 19661593147 DE19661593147 DE 19661593147 DE 1593147 A DE1593147 A DE 1593147A DE 1593147 A1 DE1593147 A1 DE 1593147A1
- Authority
- DE
- Germany
- Prior art keywords
- cyclohexanols
- general formula
- compounds
- tert
- atom
- 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.)
- Pending
Links
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical class OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 title description 9
- 239000003814 drug Substances 0.000 title description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 5
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000002902 organometallic compounds Chemical class 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 150000004696 coordination complex Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- HPXRVTGHNJAIIH-PTQBSOBMSA-N cyclohexanol Chemical group O[13CH]1CCCCC1 HPXRVTGHNJAIIH-PTQBSOBMSA-N 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- -1 alkali metal salts Chemical class 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000008602 contraction Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229940124549 vasodilator Drugs 0.000 description 3
- 239000003071 vasodilator agent Substances 0.000 description 3
- ZUYKJZQOPXDNOK-UHFFFAOYSA-N 2-(ethylamino)-2-thiophen-2-ylcyclohexan-1-one;hydrochloride Chemical class Cl.C=1C=CSC=1C1(NCC)CCCCC1=O ZUYKJZQOPXDNOK-UHFFFAOYSA-N 0.000 description 2
- IFFPICMESYHZPQ-UHFFFAOYSA-N Prenylamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CCNC(C)CC1=CC=CC=C1 IFFPICMESYHZPQ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 210000004351 coronary vessel Anatomy 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 229960001989 prenylamine Drugs 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical compound CC1=CC=CC=C1Br QSSXJPIWXQTSIX-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- QPBHJMJXTKYEFN-UHFFFAOYSA-N 2-methyl-1-(2-propan-2-ylphenyl)cyclohexan-1-ol Chemical compound CC(C)C1=CC=CC=C1C1(O)C(C)CCCC1 QPBHJMJXTKYEFN-UHFFFAOYSA-N 0.000 description 1
- LFSAPCRASZRSKS-UHFFFAOYSA-N 2-methylcyclohexan-1-one Chemical compound CC1CCCCC1=O LFSAPCRASZRSKS-UHFFFAOYSA-N 0.000 description 1
- IXVGVVQGNQZQGD-UHFFFAOYSA-N 2-propan-2-ylcyclohexan-1-ol Chemical compound CC(C)C1CCCCC1O IXVGVVQGNQZQGD-UHFFFAOYSA-N 0.000 description 1
- SDJUYPUXVFDUFF-UHFFFAOYSA-N 2-propan-2-ylcyclohexan-1-one Chemical compound CC(C)C1CCCCC1=O SDJUYPUXVFDUFF-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 206010047141 Vasodilatation Diseases 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 239000003218 coronary vasodilator agent Substances 0.000 description 1
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical class O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000007688 edging Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000009090 positive inotropic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000036279 refractory period Effects 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1096565A GB1088114A (en) | 1965-03-15 | 1965-03-15 | Aminoethyl ethers of cyclohexanols |
| GB1092665A GB1088113A (en) | 1965-03-15 | 1965-03-15 | Cyclohexanol derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1593147A1 true DE1593147A1 (de) | 1970-05-06 |
Family
ID=26247857
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661593147 Pending DE1593147A1 (de) | 1965-03-15 | 1966-03-14 | Cyclohexanole,Verfahren zu ihrer Herstellung und Arzneimittel mit einem Gehalt an diesen Verbindungen |
| DE19661593146 Pending DE1593146A1 (de) | 1965-03-15 | 1966-03-14 | Cyclohexanolaminoaethylaether und Verfahren zu ihrer Herstellung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661593146 Pending DE1593146A1 (de) | 1965-03-15 | 1966-03-14 | Cyclohexanolaminoaethylaether und Verfahren zu ihrer Herstellung |
Country Status (6)
-
1965
- 1965-03-15 GB GB1096565A patent/GB1088114A/en not_active Expired
- 1965-03-15 GB GB1092665A patent/GB1088113A/en not_active Expired
-
1966
- 1966-03-14 DE DE19661593147 patent/DE1593147A1/de active Pending
- 1966-03-14 CH CH360866A patent/CH484052A/de not_active IP Right Cessation
- 1966-03-14 DE DE19661593146 patent/DE1593146A1/de active Pending
- 1966-03-14 CH CH360766A patent/CH475929A/de not_active IP Right Cessation
- 1966-03-15 FR FR1568726D patent/FR1568726A/fr not_active Expired
- 1966-03-15 BE BE677867D patent/BE677867A/xx unknown
- 1966-03-15 FR FR1568727D patent/FR1568727A/fr not_active Expired
- 1966-03-15 NL NL6603371A patent/NL6603371A/xx unknown
- 1966-03-15 BE BE677868D patent/BE677868A/xx unknown
- 1966-03-15 NL NL6603370A patent/NL6603370A/xx unknown
- 1966-06-10 FR FR64945A patent/FR6843M/fr not_active Expired
- 1966-06-10 FR FR64946A patent/FR7372M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1088113A (en) | 1967-10-25 |
| CH484052A (de) | 1970-01-15 |
| FR1568726A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-05-30 |
| NL6603371A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-09-16 |
| FR1568727A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-05-30 |
| BE677868A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-09-15 |
| BE677867A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-09-15 |
| NL6603370A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-09-16 |
| FR6843M (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-04-08 |
| GB1088114A (en) | 1967-10-25 |
| FR7372M (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-10-27 |
| DE1593146A1 (de) | 1970-07-16 |
| CH475929A (de) | 1969-07-31 |
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