NO124645B - - Google Patents

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Publication number: NO124645B
Authority: NO; Norway
Prior art keywords: mixture; mol; hours; acid; solution
Prior art date: 1968-06-12

Application number

NO2421/69A

Other languages

English (en)

Norwegian (no)

Inventor

L Sternbach

Arthur Martin Felix

R Fryer

G Archer

A Stempel

Original Assignee

Hoffmann La Roche

Priority date (The priority date 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 date listed.)

1968-06-12

Filing date

1969-06-11

Publication date

1972-05-15

1969-06-11 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1972-05-15 Publication of NO124645B publication Critical patent/NO124645B/no

Links

150000001875 compounds Chemical class 0.000 claims abstract 21
150000003839 salts Chemical class 0.000 claims abstract 14
239000002253 acid Substances 0.000 claims abstract 12
239000001257 hydrogen Substances 0.000 claims abstract 12
229910052739 hydrogen Inorganic materials 0.000 claims abstract 12
-1 benzodiazepine ester Chemical class 0.000 claims abstract 10
238000000034 method Methods 0.000 claims abstract 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 8
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract 7
238000004519 manufacturing process Methods 0.000 claims abstract 7
229910052707 ruthenium Inorganic materials 0.000 claims abstract 7
125000000217 alkyl group Chemical group 0.000 claims abstract 6
229910052736 halogen Inorganic materials 0.000 claims abstract 6
150000002367 halogens Chemical class 0.000 claims abstract 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract 4
229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 claims abstract 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract 4
239000000460 chlorine Substances 0.000 claims abstract 4
229910052801 chlorine Inorganic materials 0.000 claims abstract 4
150000002431 hydrogen Chemical class 0.000 claims abstract 4
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 3
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims abstract 2
239000012458 free base Substances 0.000 claims abstract 2
125000001188 haloalkyl group Chemical group 0.000 claims abstract 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
241000112708 Vates Species 0.000 claims 1
125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 21
239000000463 material Substances 0.000 abstract description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 39
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 21
239000000243 solution Substances 0.000 abstract 21
238000012360 testing method Methods 0.000 abstract 18
241001465754 Metazoa Species 0.000 abstract 17
239000000203 mixture Substances 0.000 abstract 17
238000002844 melting Methods 0.000 abstract 16
230000008018 melting Effects 0.000 abstract 16
241000699670 Mus sp. Species 0.000 abstract 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 12
239000000047 product Substances 0.000 abstract 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 10
238000006243 chemical reaction Methods 0.000 abstract 10
238000003756 stirring Methods 0.000 abstract 10
206010010904 Convulsion Diseases 0.000 abstract 9
230000000694 effects Effects 0.000 abstract 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 8
238000001816 cooling Methods 0.000 abstract 8
239000000126 substance Substances 0.000 abstract 8
238000002425 crystallisation Methods 0.000 abstract 7
230000008025 crystallization Effects 0.000 abstract 7
238000002474 experimental method Methods 0.000 abstract 7
238000001914 filtration Methods 0.000 abstract 7
230000007935 neutral effect Effects 0.000 abstract 7
239000007787 solid Substances 0.000 abstract 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 6
239000000706 filtrate Substances 0.000 abstract 6
239000000725 suspension Substances 0.000 abstract 6
MEXNZUOOCNBUJU-UHFFFAOYSA-N (2-chlorophenyl)-pyrimidin-2-ylmethanone Chemical compound ClC1=CC=CC=C1C(=O)C1=NC=CC=N1 MEXNZUOOCNBUJU-UHFFFAOYSA-N 0.000 abstract 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 5
241000282326 Felis catus Species 0.000 abstract 5
230000036461 convulsion Effects 0.000 abstract 5
239000003921 oil Substances 0.000 abstract 5
235000019198 oils Nutrition 0.000 abstract 5
238000000746 purification Methods 0.000 abstract 5
239000002904 solvent Substances 0.000 abstract 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 5
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 4
230000001773 anti-convulsant effect Effects 0.000 abstract 4
239000013078 crystal Substances 0.000 abstract 4
238000004821 distillation Methods 0.000 abstract 4
238000001704 evaporation Methods 0.000 abstract 4
239000011541 reaction mixture Substances 0.000 abstract 4
WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 abstract 4
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 abstract 4
CLUHZXYQKUXOOL-UHFFFAOYSA-N 1-methyl-7-nitro-5-pyrimidin-2-yl-2,3-dihydro-1,4-benzodiazepine Chemical compound C12=CC([N+]([O-])=O)=CC=C2N(C)CCN=C1C1=NC=CC=N1 CLUHZXYQKUXOOL-UHFFFAOYSA-N 0.000 abstract 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 abstract 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 3
150000001557 benzodiazepines Chemical class 0.000 abstract 3
238000009835 boiling Methods 0.000 abstract 3
239000003054 catalyst Substances 0.000 abstract 3
239000012043 crude product Substances 0.000 abstract 3
238000000354 decomposition reaction Methods 0.000 abstract 3
SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 abstract 3
230000008020 evaporation Effects 0.000 abstract 3
238000000605 extraction Methods 0.000 abstract 3
210000000548 hind-foot Anatomy 0.000 abstract 3
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 abstract 3
239000000825 pharmaceutical preparation Substances 0.000 abstract 3
238000010992 reflux Methods 0.000 abstract 3
230000001624 sedative effect Effects 0.000 abstract 3
ZAICQJHRVHLVEY-UHFFFAOYSA-N 2-(2-chlorophenyl)-2-pyrimidin-2-ylacetonitrile Chemical compound ClC1=CC=CC=C1C(C#N)C1=NC=CC=N1 ZAICQJHRVHLVEY-UHFFFAOYSA-N 0.000 abstract 2
BSFOWENCYDHTPW-UHFFFAOYSA-N 7-nitro-5-pyrimidin-2-yl-2,3-dihydro-1h-1,4-benzodiazepine Chemical compound C12=CC([N+](=O)[O-])=CC=C2NCCN=C1C1=NC=CC=N1 BSFOWENCYDHTPW-UHFFFAOYSA-N 0.000 abstract 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 abstract 2
241000124008 Mammalia Species 0.000 abstract 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 2
208000005392 Spasm Diseases 0.000 abstract 2
238000010521 absorption reaction Methods 0.000 abstract 2
229960000583 acetic acid Drugs 0.000 abstract 2
125000003277 amino group Chemical group 0.000 abstract 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
239000001961 anticonvulsive agent Substances 0.000 abstract 2
229960003965 antiepileptics Drugs 0.000 abstract 2
239000002585 base Substances 0.000 abstract 2
SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 abstract 2
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 abstract 2
239000000284 extract Substances 0.000 abstract 2
239000005457 ice water Substances 0.000 abstract 2
230000007794 irritation Effects 0.000 abstract 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 abstract 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
239000002480 mineral oil Substances 0.000 abstract 2
235000010446 mineral oil Nutrition 0.000 abstract 2
210000003205 muscle Anatomy 0.000 abstract 2
239000003158 myorelaxant agent Substances 0.000 abstract 2
229910017604 nitric acid Inorganic materials 0.000 abstract 2
230000003647 oxidation Effects 0.000 abstract 2
238000007254 oxidation reaction Methods 0.000 abstract 2
239000003208 petroleum Substances 0.000 abstract 2
239000012071 phase Substances 0.000 abstract 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
238000002360 preparation method Methods 0.000 abstract 2
230000002040 relaxant effect Effects 0.000 abstract 2
230000035939 shock Effects 0.000 abstract 2
239000012312 sodium hydride Substances 0.000 abstract 2
229910000104 sodium hydride Inorganic materials 0.000 abstract 2
235000011121 sodium hydroxide Nutrition 0.000 abstract 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 abstract 2
229910052938 sodium sulfate Inorganic materials 0.000 abstract 2
235000011152 sodium sulphate Nutrition 0.000 abstract 2
239000007858 starting material Substances 0.000 abstract 2
125000001424 substituent group Chemical group 0.000 abstract 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 2
GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical class N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 abstract 1
MRDUURPIPLIGQX-UHFFFAOYSA-N 2-(2-chlorophenyl)acetonitrile Chemical compound ClC1=CC=CC=C1CC#N MRDUURPIPLIGQX-UHFFFAOYSA-N 0.000 abstract 1
UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 abstract 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
HSJXGZBLRDYBCN-UHFFFAOYSA-N 5-pyrimidin-2-yl-1H-1,4-benzodiazepine Chemical class N1=C(N=CC=C1)C1=NC=CNC2=C1C=CC=C2 HSJXGZBLRDYBCN-UHFFFAOYSA-N 0.000 abstract 1
MGPDXXHYUGWQSW-UHFFFAOYSA-N 7-chloro-1-methyl-5-pyrimidin-2-yl-2,3-dihydro-1,4-benzodiazepine Chemical compound C12=CC(Cl)=CC=C2N(C)CCN=C1C1=NC=CC=N1 MGPDXXHYUGWQSW-UHFFFAOYSA-N 0.000 abstract 1
BQZBKGGPTRPZBA-UHFFFAOYSA-N 7-chloro-1-methyl-5-pyrimidin-2-yl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=NC=CC=N1 BQZBKGGPTRPZBA-UHFFFAOYSA-N 0.000 abstract 1
206010003591 Ataxia Diseases 0.000 abstract 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 1
IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 abstract 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
108010010803 Gelatin Proteins 0.000 abstract 1
229920000084 Gum arabic Polymers 0.000 abstract 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
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206010033799 Paralysis Diseases 0.000 abstract 1
CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 abstract 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
229910000564 Raney nickel Inorganic materials 0.000 abstract 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
238000000297 Sandmeyer reaction Methods 0.000 abstract 1
241000978776 Senegalia senegal Species 0.000 abstract 1
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KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 abstract 1
239000000205 acacia gum Substances 0.000 abstract 1
235000010489 acacia gum Nutrition 0.000 abstract 1
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125000002252 acyl group Chemical group 0.000 abstract 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
238000010171 animal model Methods 0.000 abstract 1
230000002243 anti-metrazol Effects 0.000 abstract 1
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239000008346 aqueous phase Substances 0.000 abstract 1
239000007864 aqueous solution Substances 0.000 abstract 1
229940049706 benzodiazepine Drugs 0.000 abstract 1
230000015572 biosynthetic process Effects 0.000 abstract 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
229910052794 bromium Inorganic materials 0.000 abstract 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 abstract 1
239000002775 capsule Substances 0.000 abstract 1
229910052799 carbon Inorganic materials 0.000 abstract 1
125000004432 carbon atom Chemical group C* 0.000 abstract 1
235000011089 carbon dioxide Nutrition 0.000 abstract 1
239000012876 carrier material Substances 0.000 abstract 1
239000003153 chemical reaction reagent Substances 0.000 abstract 1
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GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 abstract 1
230000002566 clonic effect Effects 0.000 abstract 1
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 1
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VNEBWJSWMVTSHK-UHFFFAOYSA-L disodium;3-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=CC2=C1 VNEBWJSWMVTSHK-UHFFFAOYSA-L 0.000 abstract 1
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
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IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
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238000002329 infrared spectrum Methods 0.000 abstract 1
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239000002504 physiological saline solution Substances 0.000 abstract 1
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239000002244 precipitate Substances 0.000 abstract 1
239000003755 preservative agent Substances 0.000 abstract 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
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230000001954 sterilising effect Effects 0.000 abstract 1
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
229940099259 vaseline Drugs 0.000 abstract 1
235000015112 vegetable and seed oil Nutrition 0.000 abstract 1
239000008158 vegetable oil Substances 0.000 abstract 1
238000009736 wetting Methods 0.000 abstract 1
239000000080 wetting agent Substances 0.000 abstract 1
239000008096 xylene Substances 0.000 abstract 1
230000008439 repair process Effects 0.000 description 3
229910001369 Brass Inorganic materials 0.000 description 2
239000010951 brass Substances 0.000 description 2
239000002184 metal Substances 0.000 description 2
238000012856 packing Methods 0.000 description 2
230000002950 deficient Effects 0.000 description 1
239000002657 fibrous material Substances 0.000 description 1
238000003780 insertion Methods 0.000 description 1
230000037431 insertion Effects 0.000 description 1
238000003801 milling Methods 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Manufacture And Refinement Of Metals (AREA)

NO2421/69A 1968-06-12 1969-06-11 NO124645B (da)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US73625068A	1968-06-12	1968-06-12

Publications (1)

Publication Number	Publication Date
NO124645B true NO124645B (da)	1972-05-15

Family

ID=24959135

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NO2421/69A NO124645B (da)	1968-06-12	1969-06-11
NO2420/69A NO123611B (da)	1968-06-12	1969-06-14

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
NO2420/69A NO123611B (da)	1968-06-12	1969-06-14

Country Status (7)

Country	Link
BR (2)	BR6909650D0 (da)
DK (1)	DK138075B (da)
ES (1)	ES368238A1 (da)
HU (1)	HU162582B (da)
IL (1)	IL32371A (da)
NO (2)	NO124645B (da)
SE (1)	SE346998B (da)

1969
- 1969-06-05 SE SE07988/69A patent/SE346998B/xx unknown
- 1969-06-06 DK DK306169AA patent/DK138075B/da unknown
- 1969-06-10 IL IL32371A patent/IL32371A/xx unknown
- 1969-06-11 BR BR209650/69A patent/BR6909650D0/pt unknown
- 1969-06-11 NO NO2421/69A patent/NO124645B/no unknown
- 1969-06-11 BR BR209649/69A patent/BR6909649D0/pt unknown
- 1969-06-11 ES ES368238A patent/ES368238A1/es not_active Expired
- 1969-06-12 HU HUHO1183A patent/HU162582B/hu unknown
- 1969-06-14 NO NO2420/69A patent/NO123611B/no unknown

Also Published As

Publication number	Publication date
DK138075C (da)	1978-12-11
ES368238A1 (es)	1971-05-01
SE346998B (da)	1972-07-24
NO123611B (da)	1971-12-20
DK138075B (da)	1978-07-10
HU162582B (da)	1973-03-28
IL32371A (en)	1972-12-29
BR6909649D0 (pt)	1973-02-22
BR6909650D0 (pt)	1973-02-22

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