CH364508A - Procédé de préparation de phénosélénazines substituées - Google Patents

Procédé de préparation de phénosélénazines substituées

Info

Publication number: CH364508A
Authority: CH; Switzerland
Prior art keywords: sep; phenoselenazine; piperazinyl; lower alkyl; group
Prior art date: 1957-02-13

Application number

CH5546558A

Other languages

English (en)

French (fr)

Inventor

Norman Craig Paul

Original Assignee

Smith Kline French Lab

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.)

1957-02-13

Filing date

1958-02-04

Publication date

1962-09-30

1958-02-04 Application filed by Smith Kline French Lab filed Critical Smith Kline French Lab

1962-09-30 Publication of CH364508A publication Critical patent/CH364508A/fr

Links

238000000034 method Methods 0.000 title claims description 15
150000005036 phenoselenazines Chemical class 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title description 3
-1 2,5-dimethylpiperazinyl group Chemical group 0.000 claims description 27
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
238000010992 reflux Methods 0.000 claims description 18
229910052757 nitrogen Inorganic materials 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 9
ILFYOWGJBKEMSK-UHFFFAOYSA-N 10h-phenoselenazine Chemical compound C1=CC=C2NC3=CC=CC=C3[Se]C2=C1 ILFYOWGJBKEMSK-UHFFFAOYSA-N 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
238000010438 heat treatment Methods 0.000 claims description 6
125000004193 piperazinyl group Chemical group 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
239000000376 reactant Substances 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
239000003849 aromatic solvent Substances 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
125000004185 ester group Chemical group 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
230000029936 alkylation Effects 0.000 claims description 2
238000005804 alkylation reaction Methods 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
125000002950 monocyclic group Chemical group 0.000 claims description 2
125000002757 morpholinyl group Chemical group 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
125000004568 thiomorpholinyl group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 3
125000002947 alkylene group Chemical group 0.000 claims 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
150000002148 esters Chemical class 0.000 claims 1
150000004820 halides Chemical class 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 44
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
239000000725 suspension Substances 0.000 description 16
229940076134 benzene Drugs 0.000 description 15
239000000243 solution Substances 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
239000002585 base Substances 0.000 description 10
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000008096 xylene Substances 0.000 description 9
239000013078 crystal Substances 0.000 description 7
238000004821 distillation Methods 0.000 description 7
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 7
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
239000000284 extract Substances 0.000 description 6
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
239000007789 gas Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
RYEDDRYHYDLXMW-UHFFFAOYSA-N 2-chloro-10h-phenoselenazine Chemical compound C1=CC=C2NC3=CC(Cl)=CC=C3[Se]C2=C1 RYEDDRYHYDLXMW-UHFFFAOYSA-N 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
238000001816 cooling Methods 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000011976 maleic acid Substances 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
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 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
VIEXQFHKRAHTQS-UHFFFAOYSA-N chloroselanyl selenohypochlorite Chemical compound Cl[Se][Se]Cl VIEXQFHKRAHTQS-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000010410 layer Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000000047 product Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
AVAOGMQOXOGNBD-UHFFFAOYSA-N 2-(trifluoromethyl)-10H-phenoselenazine Chemical compound FC(C1=CC=2NC3=CC=CC=C3[Se]C2C=C1)(F)F AVAOGMQOXOGNBD-UHFFFAOYSA-N 0.000 description 2
ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 2
NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 2
OHHIBZKYXJDQEU-UHFFFAOYSA-N 3-chloro-n-phenylaniline Chemical compound ClC1=CC=CC(NC=2C=CC=CC=2)=C1 OHHIBZKYXJDQEU-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000012458 free base Substances 0.000 description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
229910000042 hydrogen bromide Inorganic materials 0.000 description 2
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000001294 propane Substances 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
USACENUVROURRT-UHFFFAOYSA-N 1-(3-chloro-2,2-dimethylpropyl)piperidine Chemical compound ClCC(C)(C)CN1CCCCC1 USACENUVROURRT-UHFFFAOYSA-N 0.000 description 1
SPRTXTPFQKHSBG-UHFFFAOYSA-N 1-(3-chloropropyl)pyrrolidine Chemical compound ClCCCN1CCCC1 SPRTXTPFQKHSBG-UHFFFAOYSA-N 0.000 description 1
NFYKAKCFROTKMH-UHFFFAOYSA-N 2-bromo-10H-phenoselenazine Chemical compound BrC1=CC=2NC3=CC=CC=C3[Se]C=2C=C1 NFYKAKCFROTKMH-UHFFFAOYSA-N 0.000 description 1
GHVDLKXVAHGGBB-UHFFFAOYSA-N 3-ethyl-10H-phenoselenazine Chemical compound C(C)C=1C=CC=2NC3=CC=CC=C3[Se]C=2C=1 GHVDLKXVAHGGBB-UHFFFAOYSA-N 0.000 description 1
WIHSLJHYJAGGIY-UHFFFAOYSA-N 3-methoxy-10H-phenoselenazine Chemical compound COC=1C=CC=2NC3=CC=CC=C3[Se]C=2C=1 WIHSLJHYJAGGIY-UHFFFAOYSA-N 0.000 description 1
ISRFVGGMMWIYBP-UHFFFAOYSA-N 5-bromo-n,n-dimethylpentan-1-amine Chemical compound CN(C)CCCCCBr ISRFVGGMMWIYBP-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
101100113998 Mus musculus Cnbd2 gene Proteins 0.000 description 1
BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000003474 anti-emetic effect Effects 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
230000002921 anti-spasmodic effect Effects 0.000 description 1
229940125683 antiemetic agent Drugs 0.000 description 1
239000002111 antiemetic agent Substances 0.000 description 1
229940125715 antihistaminic agent Drugs 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
229940124575 antispasmodic agent Drugs 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000011230 binding agent 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
QYJXDIUNDMRLAO-UHFFFAOYSA-N butyl 4-methylbenzenesulfonate Chemical compound CCCCOS(=O)(=O)C1=CC=C(C)C=C1 QYJXDIUNDMRLAO-UHFFFAOYSA-N 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
YFSCLDWVNTUOOE-UHFFFAOYSA-L disodium ethyl acetate carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O.CCOC(C)=O YFSCLDWVNTUOOE-UHFFFAOYSA-L 0.000 description 1
AFAXGSQYZLGZPG-UHFFFAOYSA-L ethane-1,2-disulfonate Chemical compound [O-]S(=O)(=O)CCS([O-])(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-L 0.000 description 1
AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
238000010575 fractional recrystallization Methods 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
VEBXFQBZGYLQHC-UHFFFAOYSA-N n,n-diethyl-2-[2-(trifluoromethyl)phenoselenazin-10-yl]ethanamine Chemical compound C1=C(C(F)(F)F)C=C2N(CCN(CC)CC)C3=CC=CC=C3[Se]C2=C1 VEBXFQBZGYLQHC-UHFFFAOYSA-N 0.000 description 1
CSBBBLSHQYMQMP-UHFFFAOYSA-N n,n-dimethyl-3-(1-methylphenoselenazin-10-yl)propan-1-amine Chemical compound C1=CC(C)=C2N(CCCN(C)C)C3=CC=CC=C3[Se]C2=C1 CSBBBLSHQYMQMP-UHFFFAOYSA-N 0.000 description 1
NTZJGAGYJCQKCB-UHFFFAOYSA-N n,n-dimethyl-3-phenoselenazin-10-ylpropan-1-amine Chemical compound C1=CC=C2N(CCCN(C)C)C3=CC=CC=C3[Se]C2=C1 NTZJGAGYJCQKCB-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000011368 organic material Substances 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
150000004885 piperazines Chemical class 0.000 description 1
238000010791 quenching Methods 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
229910052711 selenium Inorganic materials 0.000 description 1
239000011669 selenium Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
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 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000009423 ventilation Methods 0.000 description 1

Landscapes

Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH5546558A 1957-02-13 1958-02-04 Procédé de préparation de phénosélénazines substituées CH364508A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US63986157A	1957-02-13	1957-02-13

Publications (1)

Publication Number	Publication Date
CH364508A true CH364508A (fr)	1962-09-30

Family

ID=24565865

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH5546558A CH364508A (fr)	1957-02-13	1958-02-04	Procédé de préparation de phénosélénazines substituées

Country Status (2)

Country	Link
BR (1)	BR5800372D0 (pt)
CH (1)	CH364508A (pt)

1958
- 1958-02-04 CH CH5546558A patent/CH364508A/fr unknown
- 1958-02-11 BR BR10037258A patent/BR5800372D0/pt unknown

Also Published As

Publication number	Publication date
BR5800372D0 (pt)	1973-05-24

Publication	Publication Date	Title
Wawzonek et al.	1959	The Formation of 4-chlorodibutylamine from N-chlorodibutylamine1
FR2663328A1 (fr)	1991-12-20	Derives d'hexahydroazepines, un procede pour leur preparation et compositions pharmaceutiques les contenant.
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FR2572075A1 (fr)	1986-04-25	Nouveaux derives de la 4-dioxino-(4,5-c)-pyridine et leur procede de preparation
EP0061379B1 (fr)	1985-10-02	Dérivés de pyridine, leur préparation et leur application en thérapeutique
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