BE562412A - - Google Patents

Info

Publication number: BE562412A
Authority: BE; Belgium
Prior art keywords: residue; pyridazine; salts; benzyl; desc
Prior art date

Application number

Other languages

Publication of BE562412A publication Critical patent/BE562412A/fr

Links

229910052757 nitrogen Inorganic materials 0.000 claims description 20
PBMFSQRYOILNGV-UHFFFAOYSA-N Pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 17
238000000034 method Methods 0.000 claims description 15
230000001034 aminogenic Effects 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 12
239000011780 sodium chloride Substances 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
239000007858 starting material Substances 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 8
125000000547 substituted alkyl group Chemical group 0.000 claims description 8
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 4
238000007363 ring formation reaction Methods 0.000 claims description 3
125000003916 ethylene diamine group Chemical group 0.000 claims description 2
150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
150000003947 ethylamines Chemical class 0.000 claims 1
230000002147 killing Effects 0.000 claims 1
125000004433 nitrogen atoms Chemical group N* 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 38
239000000243 solution Substances 0.000 description 37
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
235000019441 ethanol Nutrition 0.000 description 19
238000010992 reflux Methods 0.000 description 16
239000000203 mixture Substances 0.000 description 15
238000004821 distillation Methods 0.000 description 14
238000002844 melting Methods 0.000 description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
239000001184 potassium carbonate Substances 0.000 description 10
229910000027 potassium carbonate Inorganic materials 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
238000003756 stirring Methods 0.000 description 8
239000002253 acid Substances 0.000 description 7
238000001816 cooling Methods 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
239000000155 melt Substances 0.000 description 7
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 7
229910052753 mercury Inorganic materials 0.000 description 7
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
238000005292 vacuum distillation Methods 0.000 description 7
FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
239000003610 charcoal Substances 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
229940086542 triethylamine Drugs 0.000 description 6
238000009835 boiling Methods 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
230000001264 neutralization Effects 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
238000010521 absorption reaction Methods 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
-1 heterocyclic carboxylic Chemical class 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
239000007868 Raney catalyst Substances 0.000 description 3
229910000564 Raney nickel Inorganic materials 0.000 description 3
239000003929 acidic solution Substances 0.000 description 3
230000001476 alcoholic Effects 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000001273 butane Substances 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
230000000875 corresponding Effects 0.000 description 3
125000004185 ester group Chemical group 0.000 description 3
239000008079 hexane Substances 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
LJDQXQOPXOLCHL-UHFFFAOYSA-N 3,4,6-trichloropyridazine Chemical compound ClC1=CC(Cl)=C(Cl)N=N1 LJDQXQOPXOLCHL-UHFFFAOYSA-N 0.000 description 2
FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N Perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N Phenylacetic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
229910000831 Steel Inorganic materials 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N al2o3 Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
239000006187 pill Substances 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
150000004892 pyridazines Chemical class 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000010959 steel Substances 0.000 description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N 1,2-ethanediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
XNIOWJUQPMKCIJ-UHFFFAOYSA-N 2-(benzylamino)ethanol Chemical compound OCCNCC1=CC=CC=C1 XNIOWJUQPMKCIJ-UHFFFAOYSA-N 0.000 description 1
ONRREFWJTRBDRA-UHFFFAOYSA-N 2-chloroethanamine;hydron;chloride Chemical compound [Cl-].[NH3+]CCCl ONRREFWJTRBDRA-UHFFFAOYSA-N 0.000 description 1
JADVVTZXHQUFLS-UHFFFAOYSA-N 3,4-dichloropyridazine Chemical compound ClC1=CC=NN=C1Cl JADVVTZXHQUFLS-UHFFFAOYSA-N 0.000 description 1
WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-Methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 1
QVNVGTVAPQGSOF-UHFFFAOYSA-L 3-[4-(9,9-dimethyl-3-aza-9-azoniabicyclo[3.3.1]nonan-3-yl)butyl]-9,9-dimethyl-3-aza-9-azoniabicyclo[3.3.1]nonane;diiodide Chemical compound [I-].[I-].C1C([N+]2(C)C)CCCC2CN1CCCCN(C1)CC2CCCC1[N+]2(C)C QVNVGTVAPQGSOF-UHFFFAOYSA-L 0.000 description 1
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
AHHSESPYBKIBKV-UHFFFAOYSA-N CN(CC(CC)NCC1=CC=CC=C1)C Chemical compound CN(CC(CC)NCC1=CC=CC=C1)C AHHSESPYBKIBKV-UHFFFAOYSA-N 0.000 description 1
XCOOKYXIONGNLN-UHFFFAOYSA-N CN(CCN=CC1=CC=CC=C1)CC1=CC=CC=C1 Chemical compound CN(CCN=CC1=CC=CC=C1)CC1=CC=CC=C1 XCOOKYXIONGNLN-UHFFFAOYSA-N 0.000 description 1
210000003169 Central Nervous System Anatomy 0.000 description 1
241001647328 Gardenia taitensis Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
SKRDXYBATCVEMS-UHFFFAOYSA-N Isopropyl nitrite Chemical compound CC(C)ON=O SKRDXYBATCVEMS-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-UUNJERMWSA-N Lactose Natural products O([C@@H]1[C@H](O)[C@H](O)[C@H](O)O[C@@H]1CO)[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1 GUBGYTABKSRVRQ-UUNJERMWSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
NUDIHLZKQUGACI-UHFFFAOYSA-N N',N'-diethyl-N-[(3-methoxyphenyl)methyl]ethane-1,2-diamine Chemical compound CCN(CC)CCNCC1=CC=CC(OC)=C1 NUDIHLZKQUGACI-UHFFFAOYSA-N 0.000 description 1
RIWRFSMVIUAEBX-UHFFFAOYSA-N N-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
210000004940 Nucleus Anatomy 0.000 description 1
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Natural products CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
230000002378 acidificating Effects 0.000 description 1
238000007792 addition Methods 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
125000004429 atoms Chemical group 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
150000003938 benzyl alcohols Chemical class 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
QUSNBJAOOMFDIB-UHFFFAOYSA-N ethyl amine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
230000005284 excitation Effects 0.000 description 1
230000001747 exhibiting Effects 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
125000004435 hydrogen atoms Chemical group [H]* 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
UWYVPFMHMJIBHE-OWOJBTEDSA-N hydroxymaleic acid group Chemical group O/C(/C(=O)O)=C/C(=O)O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 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
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004899 motility Effects 0.000 description 1
150000002829 nitrogen Chemical group 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
230000002335 preservative Effects 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000004717 pyruvic acids Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000021 stimulant Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
125000004434 sulfur atoms Chemical group 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Landscapes

Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

BE562412D BE562412A (cs)

Publications (1)

Publication Number	Publication Date
BE562412A true BE562412A (cs)

Family

ID=184017

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE562412D BE562412A (cs)

Country Status (1)

Country	Link
BE (1)	BE562412A (cs)

0
- BE BE562412D patent/BE562412A/fr unknown

Similar Documents

Publication	Publication Date	Title
CH616647A5 (cs)	1980-04-15
BE562412A (cs)
EP0067094B1 (fr)	1985-10-02	Dérivés hétérocycliques d'amidoximes, leur préparation et leur application en thérapeutique
CH641764A5 (fr)	1984-03-15	Sels d'imidoesters et procede de synthese de 2-naphtalene-ethanimidamide n,n'-disubstitues a partir desdits sels.
EP0354078B1 (fr)	1993-03-10	Nouveaux dérivés du benzocycloheptène, leur procédé de préparation et les compositions pharmaceutiques les renfermant
BE642084A (cs)
BE583205A (cs)
BE569836A (cs)
BE500594A (cs)
BE632562A (cs)
BE505305A (cs)
BE482321A (cs)
CH420107A (fr)	1966-09-15	Procédé de préparation de nouveaux dérivés d'aralcoylaminoalcoylcyclohexanes substitués
BE500675A (cs)
BE533997A (cs)
BE896927A (fr)	1983-12-02	Derives d'isoquinoleine, leur procede de preparation et medicament les contenant
BE442051A (cs)
CH589086A5 (en)	1977-06-30	Phthalazino(2,3-b)phthalazine-5,12-dione prepn - from 2-benzyl-3,4-dihydro-1(2H)-phthalazinone
BE441883A (cs)
BE569076A (cs)
BE562880A (cs)
CH311406A (fr)	1955-11-30	Procédé de préparation de la 1-carbobenzoxy-4-carbamyl-pipérazine.
CH354084A (fr)	1961-05-15	Procédé de préparation de pipérazines
BE480546A (cs)	1948-03-15
BE520993A (cs)