DE1543771A1 - 2-Hydroxy-3-subst.-propyl-1,4'-naphthochinone und Verfahren zu deren Herstellung - Google Patents
2-Hydroxy-3-subst.-propyl-1,4'-naphthochinone und Verfahren zu deren HerstellungInfo
- Publication number
- DE1543771A1 DE1543771A1 DE19661543771 DE1543771A DE1543771A1 DE 1543771 A1 DE1543771 A1 DE 1543771A1 DE 19661543771 DE19661543771 DE 19661543771 DE 1543771 A DE1543771 A DE 1543771A DE 1543771 A1 DE1543771 A1 DE 1543771A1
- Authority
- DE
- Germany
- Prior art keywords
- hydroxy
- preparation
- hydrogen
- substituted
- naphthoquinones
- 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
- 238000000034 method Methods 0.000 title claims description 12
- -1 4-phenoxyphenyl Chemical group 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- IWTBWSGPDGPTIB-UHFFFAOYSA-N butanoyl butaneperoxoate Chemical compound CCCC(=O)OOC(=O)CCC IWTBWSGPDGPTIB-UHFFFAOYSA-N 0.000 claims description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 239000008186 active pharmaceutical agent Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 244000144977 poultry Species 0.000 description 5
- 229930192627 Naphthoquinone Natural products 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000002791 naphthoquinones Chemical class 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-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
- 238000006243 chemical reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000003495 Coccidiosis Diseases 0.000 description 1
- 241000223924 Eimeria Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 206010023076 Isosporiasis Diseases 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 238000006856 Wolf-Kishner-Huang Minlon reduction reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical class CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/26—Quinones containing groups having oxygen atoms singly bound to carbon atoms
- C07C50/32—Quinones containing groups having oxygen atoms singly bound to carbon atoms the quinoid structure being part of a condensed ring system having two rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Fodder In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US487304A US3393211A (en) | 1965-09-14 | 1965-09-14 | Naphthoquinone compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1543771A1 true DE1543771A1 (de) | 1969-11-27 |
Family
ID=23935197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661543771 Pending DE1543771A1 (de) | 1965-09-14 | 1966-09-13 | 2-Hydroxy-3-subst.-propyl-1,4'-naphthochinone und Verfahren zu deren Herstellung |
Country Status (7)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005054989A1 (de) * | 2005-11-16 | 2007-05-24 | Kabe-Labortechnik Gmbh | Blutentnahmevorrichtung |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4485117A (en) * | 1981-10-16 | 1984-11-27 | Hudson Alan T | Antiprotozoal compounds |
| US4485116A (en) * | 1981-10-16 | 1984-11-27 | Hudson Alan T | Antiprotozoal compounds |
| GB2159056A (en) * | 1984-04-04 | 1985-11-27 | Alan Alaexander Torrance Sime | Biocidal compositions comprising polyhydroxynaphthoquinones |
-
1965
- 1965-09-14 US US487304A patent/US3393211A/en not_active Expired - Lifetime
-
1966
- 1966-09-05 FR FR75233A patent/FR1509950A/fr not_active Expired
- 1966-09-05 GB GB39537/66A patent/GB1091810A/en not_active Expired
- 1966-09-05 CH CH1281866A patent/CH472355A/de unknown
- 1966-09-12 BR BR182775/66A patent/BR6682775D0/pt unknown
- 1966-09-12 NL NL6612826A patent/NL6612826A/xx unknown
- 1966-09-13 DE DE19661543771 patent/DE1543771A1/de active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005054989A1 (de) * | 2005-11-16 | 2007-05-24 | Kabe-Labortechnik Gmbh | Blutentnahmevorrichtung |
Also Published As
| Publication number | Publication date |
|---|---|
| BR6682775D0 (pt) | 1973-10-25 |
| FR1509950A (fr) | 1968-01-19 |
| NL6612826A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-03-15 |
| GB1091810A (en) | 1967-11-22 |
| CH472355A (de) | 1969-05-15 |
| US3393211A (en) | 1968-07-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1770171C3 (de) | 2,2-Dimethyl-7-alkyl-4-(4-pyridyl)-2H-chromen-5-ole, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneipräparate | |
| DE1543771A1 (de) | 2-Hydroxy-3-subst.-propyl-1,4'-naphthochinone und Verfahren zu deren Herstellung | |
| DE1795809C2 (de) | 2-Methyl-3-hydroxy-4-hydroxymethyl-5-alkyl-mercaptomethyl-pyridine | |
| DE1595964A1 (de) | Phenylessigsaeuren und Verfahren zu deren Herstellung | |
| DE1695428A1 (de) | Neue schwefelhaltige Pyridinderivate und Verfahren zu deren Herstellung | |
| DE2461069A1 (de) | Neue cholesterinsenkende verbindungen | |
| DE1543764A1 (de) | Phenoxysubstituierte Alkansaeuren und Verfahren zu deren Herstellung | |
| DE1795402A1 (de) | Amidderivate der 1-Piperazinoessigsaeureester und Verfahren zu ihrer Herstellung | |
| DE2038836C3 (de) | Arzneimittel | |
| DE664789C (de) | Verfahren zur Herstellung von 4-Methyl-5-ª‰-oxyaethylthiazolen | |
| DE1595916A1 (de) | 1,3-AEthanopiperazin und seine Saeureadditionssalze und ein Verfahren zur Herstellung dieser Verbindungen | |
| DE1695855B2 (de) | 4-(5-Isobutyl-2-pyrimidinyl)-sulfonamidophenylessigsäure-(2-methoxy-5-Chloranilid) und dessen Salze mit physiologisch verträglichen Basen | |
| DE1768366C3 (de) | 3-Hydroxy-alpha-(l-aminoäthyl)benzylalkohol-derivate und diese enthaltende Arzneimittel | |
| DE1253717C2 (de) | Verfahren zur herstellung von o,s-dialkoxycarbonyl-vitamin b tief 1derivaten | |
| DE2327659C2 (de) | Phenoxycarbonsäurederivate und sie enthaltende Arzneimittel | |
| DE2237732C2 (de) | trans-1-(3-Benzoyloxystyryl)-pyridiniumsalze und ihre Verwendung | |
| DE1952800B2 (de) | 3,6-dimethyl-1,2,3,4,4a,9a-hexahydro-gamma-carbolin-dihydrochlorid | |
| DE2263121C3 (de) | Alkyl-2,3,3-trijodallyläther, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln | |
| AT250933B (de) | Verfahren zur Herstellung von neuen Carbonsäuren | |
| DE1543185A1 (de) | Acylphenole und Verfahren zu deren Herstellung | |
| DE1468340A1 (de) | Phenoxyessigsaeureverbindungen und Verfahren zu ihrer Herstellung | |
| DE2238260C3 (de) | Phosphorsäuremonoester von 5-(2-Dimethylaminoäthoxy)-carvacrol, Verfahren zu seiner Herstellung und diesen enthaltende Arzneimittel | |
| DE2164988A1 (de) | Neue Ester der Diaryl-2,2-cyclopropancarbonsäure | |
| DE2533806B2 (de) | Choleretisches Mittel | |
| DE2120396A1 (en) | 3-alkoxy-1-phenoxypropanols contg medicaments - as choleretics |