DE2023400A1 - - Google Patents
Info
- Publication number
- DE2023400A1 DE2023400A1 DE19702023400 DE2023400A DE2023400A1 DE 2023400 A1 DE2023400 A1 DE 2023400A1 DE 19702023400 DE19702023400 DE 19702023400 DE 2023400 A DE2023400 A DE 2023400A DE 2023400 A1 DE2023400 A1 DE 2023400A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compound
- acid
- oxide
- phenazinediol
- 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
- 150000001875 compounds Chemical class 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 17
- 125000006239 protecting group Chemical group 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 150000002988 phenazines Chemical class 0.000 claims description 5
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- ZXBAHZGKYRGBPG-UHFFFAOYSA-N 5,6-dihydroxyphenazin-1-one Chemical compound ON1C=2C(O)=CC=CC=2N=C2C1=CC=CC2=O ZXBAHZGKYRGBPG-UHFFFAOYSA-N 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- -1 benzyl halides Chemical class 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- NBMOVCYIGUDQJE-UHFFFAOYSA-N iodinin Chemical compound C1=CC=C2[N+]([O-])=C3C(O)=CC=CC3=[N+]([O-])C2=C1O NBMOVCYIGUDQJE-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 230000000845 anti-microbial effect Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229940061627 chloromethyl methyl ether Drugs 0.000 description 2
- 230000020335 dealkylation Effects 0.000 description 2
- 238000006900 dealkylation reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000002070 germicidal effect Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000001119 stannous chloride Substances 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OTVHGXNVYMIHFH-UHFFFAOYSA-N C1=CC=C2N=C3C(O)=CC=CC3=[N+]([O-])C2=C1O Chemical compound C1=CC=C2N=C3C(O)=CC=CC3=[N+]([O-])C2=C1O OTVHGXNVYMIHFH-UHFFFAOYSA-N 0.000 description 1
- JFELGJFMCAJVQT-UHFFFAOYSA-N COC1=C2[N+](=C3C=CC=C(C3=NC2=CC=C1)O)[O-] Chemical compound COC1=C2[N+](=C3C=CC=C(C3=NC2=CC=C1)O)[O-] JFELGJFMCAJVQT-UHFFFAOYSA-N 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000187481 Mycobacterium phlei Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical class OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- CZPZWMPYEINMCF-UHFFFAOYSA-N propaneperoxoic acid Chemical compound CCC(=O)OO CZPZWMPYEINMCF-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
- C07D241/52—Oxygen atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00824695A US3822265A (en) | 1966-11-25 | 1969-05-14 | Phenazine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2023400A1 true DE2023400A1 (en, 2012) | 1970-11-19 |
Family
ID=25242099
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702023400 Pending DE2023400A1 (en, 2012) | 1969-05-14 | 1970-05-13 |
Country Status (8)
| Country | Link |
|---|---|
| AU (1) | AU1436170A (en, 2012) |
| BE (1) | BE750206A (en, 2012) |
| CH (1) | CH532589A (en, 2012) |
| DE (1) | DE2023400A1 (en, 2012) |
| FR (1) | FR2060320B1 (en, 2012) |
| GB (1) | GB1254836A (en, 2012) |
| IL (1) | IL34402A0 (en, 2012) |
| NL (1) | NL7006841A (en, 2012) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1525622A (fr) * | 1966-06-03 | 1968-05-17 | Canadian Patents Dev | Procédé de préparation de phénazines substituées |
| CH521358A (de) * | 1966-11-25 | 1972-04-15 | Hoffmann La Roche | Verfahren zur Herstellung von Phenazinderivaten |
| US3432505A (en) * | 1967-03-17 | 1969-03-11 | Abbott Lab | Process for amking 1-hydroxy-6-alkoxyphenazine-5,10-dioxides |
-
1970
- 1970-04-24 CH CH617370A patent/CH532589A/de not_active IP Right Cessation
- 1970-04-27 AU AU14361/70A patent/AU1436170A/en not_active Expired
- 1970-04-29 IL IL34402A patent/IL34402A0/xx unknown
- 1970-05-11 BE BE750206D patent/BE750206A/xx unknown
- 1970-05-12 GB GB22805/70A patent/GB1254836A/en not_active Expired
- 1970-05-12 NL NL7006841A patent/NL7006841A/xx unknown
- 1970-05-13 FR FR7017383A patent/FR2060320B1/fr not_active Expired
- 1970-05-13 DE DE19702023400 patent/DE2023400A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL7006841A (en, 2012) | 1970-11-17 |
| CH532589A (de) | 1973-01-15 |
| GB1254836A (en) | 1971-11-24 |
| AU1436170A (en) | 1971-10-28 |
| FR2060320A1 (en, 2012) | 1971-06-18 |
| IL34402A0 (en) | 1970-06-17 |
| BE750206A (fr) | 1970-11-12 |
| FR2060320B1 (en, 2012) | 1974-04-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69230278T2 (de) | Verfahren zur Herstellung von Omeprazol | |
| DE2006472A1 (de) | Furan-3-carboxamid-Derivate und Verfahren zu ihrer Herstellung | |
| DE2023400A1 (en, 2012) | ||
| DE2008578A1 (de) | Verfahren zur Herstellung von Nifcrosoharnstof1/erbindungen | |
| DE19904310A1 (de) | Verfahren zur Herstellung heterocyclischer Verbindungen | |
| CH512500A (de) | Verfahren zur Herstellung von Phenazin-Derivaten | |
| DE2823712C2 (de) | Verfahren zur Herstellung von Pleuromutilin-Derivaten | |
| DE1197887B (de) | Verfahren zur Herstellung von 3-Trifluormethylphenoxazinderivaten | |
| DE1236518B (de) | Verfahren zur Herstellung von Tetraalkylammoniumalanaten | |
| DE2113254C3 (de) | Verfahren zur Herstellung von γ-Piperidinoburyrophenonderivaten | |
| DE1912729A1 (de) | Verfahren zur Herstellung von Sulfoxiden | |
| EP0033830B1 (de) | Verfahren zur Herstellung polycyclischer stickstoffhaltiger Verbindungen | |
| DE1925423C (de) | 2,2-Dimethyl-omega-aryloxy alkansäuren und deren Derivate | |
| DE2210113A1 (de) | Benzimidazolylsulfide und -sulfone, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE947165C (de) | Verfahren zur Herstellung von in 3-Stellung substituierten 4-Oxycumarinen | |
| DE1695080A1 (de) | Verfahren zur Herstellung von neuen N-heterocyclischen Verbindungen | |
| DE1207381B (de) | Verfahren zur Herstellung von 2-Hydroxy-2-methylmercapto-indandion-(1, 3) | |
| DE948974C (de) | Verfahren zur Herstellung von cyclischen 4-Halogenpregnan-3, 20-dion-3, 20-diketalen | |
| DE935365C (de) | Verfahren zur Herstellung von Ketoverbindungen | |
| DD232493A5 (de) | Verfahren zur herstellung von kondensierten as-triazin-derivaten | |
| DE2319518A1 (de) | Terpenische 2-methylbutadienylsulfone | |
| DE1267219B (de) | Verfahren zur Abtrennung von 17alpha-AEthinyl-19-nor-delta 4-androsten-17beta-ol-3-on | |
| DE2624923A1 (de) | Derivate des chinoxalin-1,4- dioxids | |
| DE1144728B (de) | Verfahren zur Herstellung von Mono- und Bis-dihalogenacetyl-aryl-verbindungen | |
| DE1620395A1 (de) | Verfahren zur Herstellung von Cycloheptimidazoliniumhalogeniden |