CH514554A - Quinazolinone derivs - with antiphlogistic props - Google Patents
Quinazolinone derivs - with antiphlogistic propsInfo
- Publication number
- CH514554A CH514554A CH1242671A CH1242671A CH514554A CH 514554 A CH514554 A CH 514554A CH 1242671 A CH1242671 A CH 1242671A CH 1242671 A CH1242671 A CH 1242671A CH 514554 A CH514554 A CH 514554A
- Authority
- CH
- Switzerland
- Prior art keywords
- degrees
- alkyl
- inert solvent
- alkoxy
- formula
- Prior art date
Links
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical compound C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 title abstract 2
- 230000001741 anti-phlogistic effect Effects 0.000 title abstract 2
- 239000002260 anti-inflammatory agent Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 6
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Chemical group 0.000 claims description 5
- 150000004699 copper complex Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000011737 fluorine Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 abstract 3
- -1 alkyl carbamates Chemical class 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 abstract 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 abstract 2
- DLGOLDCIEHQIMN-UHFFFAOYSA-N 2-(benzenecarboximidoyl)aniline Chemical class NC1=CC=CC=C1C(=N)C1=CC=CC=C1 DLGOLDCIEHQIMN-UHFFFAOYSA-N 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 abstract 1
- CTOUNZIAEBIWAW-UHFFFAOYSA-N 3,4-dihydro-1h-quinazolin-2-one Chemical class C1=CC=C2NC(=O)NCC2=C1 CTOUNZIAEBIWAW-UHFFFAOYSA-N 0.000 abstract 1
- VGNAMTKXQSLQJZ-UHFFFAOYSA-N 3,4-dihydro-1h-quinazoline-2-thione Chemical class C1=CC=C2NC(=S)NCC2=C1 VGNAMTKXQSLQJZ-UHFFFAOYSA-N 0.000 abstract 1
- WQXRCWWWLAZOMX-UHFFFAOYSA-N 3-(benzenecarboximidoyl)-6-methyl-2-propan-2-ylaniline Chemical compound C(C)(C)C1=C(C(C2=CC=CC=C2)=N)C=CC(=C1N)C WQXRCWWWLAZOMX-UHFFFAOYSA-N 0.000 abstract 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract 1
- 206010061218 Inflammation Diseases 0.000 abstract 1
- 239000002841 Lewis acid Substances 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- 241001061127 Thione Species 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 1
- 230000004054 inflammatory process Effects 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 3
- QGBSLPHQCUIZKK-UHFFFAOYSA-N 4-methyl-2-nitrobenzonitrile Chemical compound CC1=CC=C(C#N)C([N+]([O-])=O)=C1 QGBSLPHQCUIZKK-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- NWESJZZPAJGHRZ-UHFFFAOYSA-N 1-chloro-4-methyl-2-nitrobenzene Chemical compound CC1=CC=C(Cl)C([N+]([O-])=O)=C1 NWESJZZPAJGHRZ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229940045348 brown mixture Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/80—Oxygen atoms
- C07D239/82—Oxygen atoms with an aryl radical attached in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B27/00—Optical systems or apparatus not provided for by any of the groups G02B1/00 - G02B26/00, G02B30/00
- G02B27/02—Viewing or reading apparatus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Medicinal Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Quinazolinone derivs with antiphlogistic properties.. G3A. are of formula (I): (where R = H, F, Cl, Br, alkyl with 1 to 5C, alkoxy or alkylthio with 1 to 4C, NO2, CN or CF3; n = 1 or 2, and in the latter case, the two R's may be same or different; R1 = alkyl with 1 to 5C, allyl or propargyl; and R2 = phenyl opt. substd. with one or two F, Cl, Br, alkyl, or alkoxy gps. or by one CF3 group) and are prepared (a) from appropriate aminobenzophenoneimines, (esp. 2-isopropyl-amino-4-methylbenzophenonimine, II), provided that R1 is not tert-alkyl, by cyclisation with methyl or pref. ethyl chlorocarbonate at 60-100 degrees C in the presence of an inert solvent and a base; or with lower alkyl carbamates, particularly excess urethane, and a Lewis acid at 160-80 degrees; or with 1,1'-carbonyldiimidazole in an inert solvent at 60-90 degrees; or with phosgene in the presence of a base and an inert solvent at 10-30 degrees; or (b) corresp. 3,4-dihydroquinazolinones are oxidised with MnO2 or MnO4 at 15-30 degrees, or the analogous thiones are hydrolysed with aqueous alkali at 80-120 degrees; or 3,4-dihydroquinazoline-2-thiones are treated with MnO4 at 0-60 degrees. The products (I) have valuable pharmacological properties, and can be used orally or parenterally in pharmaceutical preparations to reduce inflammation; cpds. such as (II) are also excellent analgetics.
Description
Verfahren zur Herstellung von 2-Nitrobenzonitrilen
Die Erfindung betrifft ein Verfahren zur Herstellung von 2-Nitrobenzonitrilen der Formel I,
EMI1.1
worin R Wasserstoff, Fluor, Chlor, Brom, Alkyl mit 1-5 Kohlenstoffatomen, Alkoxy oder Alkylthio mit je 14 Kohlenstoffatomen oder Trifluormethyl bedeutet und n für 1 oder 2 steht, wobei - falls n für 2 steht die Substituenten R gleich oder verschieden sein können und jeweils Wasserstoff, Halogen, Alkyl oder Alkoxy bedeuten.
Das erfindungsgemässe Verfahren ist dadurch gekennzeichnet, dass man l-Halogen-2-nitrobenzole der Formel II,
EMI1.2
worin R und n obige Bedeutung besitzen und X für Fluor, Chlor oder Brom steht, mit Kupfer-I-cyanid umsetzt und den dabei erhaltenen Kupferkomplex zersetzt.
Die Umsetzung von Verbindungen der Formel II mit Kupfer-I-cyanid wird zweckmässigerweise bei erhöhter Temperatur und in Gegenwart eines inerten organischen Lösungsmittels durchgeführt. Die Reaktionstemperatur kann beispielsweise 100 bis 2200 C, vorzugsweise 130 bis 1800 C, betragen. Als bevorzugte Lösungsmittel verwendet man solche, die innerhalb des bevorzugten Bereiches der Reaktionstemperaturen sieden, so dass man unter Rückfluss arbeiten kann, z. B.
Dimethylacetamid oder Dimethylformamid, vorzugsweise Dimethylacetamid. Das Molverhältnis von Kupfer-I-cyanid zu den Verbindungen der Formel II in dem Reaktionsgemisch ist nicht kritisch; normalerweise liegt es bei etwa der stöchiometrisch zur Bildung des gewünschten Produktes erforderlichen Menge bis hinauf zu einem schwachen Überschuss. Die Reaktionszeit beträgt etwa 1 bis 10 Stunden. Der Substituent X bei Verbindungen der Formel II ist vorzugsweise Chlor.
Die Zersetzung des entstandenen Kupferkomplexes kann beispielsweise durch Zugabe von Methylenchlorid erfolgen.
Die Verbindungen der Formel II sind entweder bekannt oder können in bekannter Weise hergestellt werden.
Die Verbindungen der Formel I stellen Zwischenprodukte dar und können beispielsweise zur Herstellung wertvoller Pharmazeutika verwendet werden.
Beispiel 4-Methyl-2 -nitrobenzonitril
Ein Gemisch aus 100 g 4-Chlor-3-nitrotoluol, 60 g Kupfer-I-cyanid und 150 ml Dimethylacetamid wird 4 t/2 Stunden unter Rückfluss erhitzt. Das dabei erhaltene braune Gemisch giesst man auf 1000 ml Eiswasser, filtriert es zur Abtrennung des ausgefallenen dunkelbraunen Kupferkomplexes und zersetzt diesen dann durch Behandlung mit 600 ml Methylenchlorid unter Rühren bei Zimmertemperatur. Das unlösliche anorganische Material wird abfiltriert, worauf man das Filtrat über wasserfreiem Natriumsulfat trocknet, mit 5 g Aktivkohle und 50 g Aluminiumoxyd behandelt und erneut zur Entfemung unlöslichen Materials abfiltriert.
Das Filtrat wird im Vakuum zur Trockene eingedampft, und der dabei erhaltene rohe kristalline Rückstand ergibt nach Umkristallisieren aus Diäthyläther das 4 Methyl-2-nitrobenzonitril vom Smp. 96-97 C.
Process for the preparation of 2-nitrobenzonitriles
The invention relates to a process for the preparation of 2-nitrobenzonitriles of the formula I,
EMI1.1
where R is hydrogen, fluorine, chlorine, bromine, alkyl with 1-5 carbon atoms, alkoxy or alkylthio with 14 carbon atoms each or trifluoromethyl and n is 1 or 2, where - if n is 2, the substituents R can be identical or different and each represent hydrogen, halogen, alkyl or alkoxy.
The inventive method is characterized in that l-halo-2-nitrobenzenes of the formula II,
EMI1.2
where R and n have the above meanings and X is fluorine, chlorine or bromine, reacts with copper-I-cyanide and decomposes the copper complex obtained in this way.
The reaction of compounds of the formula II with copper (I) cyanide is expediently carried out at an elevated temperature and in the presence of an inert organic solvent. The reaction temperature can be, for example, 100 to 2200 C, preferably 130 to 1800 C. The preferred solvents used are those which boil within the preferred range of reaction temperatures so that reflux can be carried out, e.g. B.
Dimethylacetamide or dimethylformamide, preferably dimethylacetamide. The molar ratio of copper (I) cyanide to the compounds of the formula II in the reaction mixture is not critical; normally it will be from about the stoichiometrically required amount to form the desired product up to a slight excess. The reaction time is about 1 to 10 hours. The substituent X in compounds of the formula II is preferably chlorine.
The copper complex formed can be decomposed, for example, by adding methylene chloride.
The compounds of the formula II are either known or can be prepared in a known manner.
The compounds of the formula I are intermediates and can be used, for example, for the production of valuable pharmaceuticals.
Example 4-methyl-2-nitrobenzonitrile
A mixture of 100 g of 4-chloro-3-nitrotoluene, 60 g of copper (I) cyanide and 150 ml of dimethylacetamide is refluxed for 4 t / 2 hours. The brown mixture obtained is poured into 1000 ml of ice water, filtered to separate the precipitated dark brown copper complex and then decomposed by treatment with 600 ml of methylene chloride with stirring at room temperature. The insoluble inorganic material is filtered off, whereupon the filtrate is dried over anhydrous sodium sulfate, treated with 5 g of activated charcoal and 50 g of aluminum oxide and filtered again to remove the insoluble material.
The filtrate is evaporated to dryness in vacuo, and the crude crystalline residue obtained after recrystallization from diethyl ether gives 4-methyl-2-nitrobenzonitrile with a melting point of 96-97 C.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74180768A | 1968-07-01 | 1968-07-01 | |
| US74180668A | 1968-07-01 | 1968-07-01 | |
| CH894669A CH514597A (en) | 1968-07-01 | 1969-06-12 | Quinazolinone derivs - with antiphlogistic props |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH514554A true CH514554A (en) | 1971-10-31 |
Family
ID=27176095
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1242671A CH514554A (en) | 1968-07-01 | 1969-06-12 | Quinazolinone derivs - with antiphlogistic props |
| CH1242071A CH514603A (en) | 1968-07-01 | 1969-06-12 | Process for the preparation of new 4-phenyl-2 (1H) -quinazolinones |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1242071A CH514603A (en) | 1968-07-01 | 1969-06-12 | Process for the preparation of new 4-phenyl-2 (1H) -quinazolinones |
Country Status (1)
| Country | Link |
|---|---|
| CH (2) | CH514554A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0110559A1 (en) * | 1982-11-26 | 1984-06-13 | Sanwa Kagaku Kenkyusho Co., Ltd. | Process for the preparation of 4-chloro-2-nitrobenzonitrile |
-
1969
- 1969-06-12 CH CH1242671A patent/CH514554A/en not_active IP Right Cessation
- 1969-06-12 CH CH1242071A patent/CH514603A/en not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0110559A1 (en) * | 1982-11-26 | 1984-06-13 | Sanwa Kagaku Kenkyusho Co., Ltd. | Process for the preparation of 4-chloro-2-nitrobenzonitrile |
Also Published As
| Publication number | Publication date |
|---|---|
| CH514603A (en) | 1971-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |