NL8004537A - Heterocyclische verbindingen. - Google Patents

Heterocyclische verbindingen. Download PDF

Info

Publication number: NL8004537A
Authority: NL; Netherlands
Prior art keywords: formula; compound; compounds; cis; acid
Prior art date: 1979-08-17

Application number

NL8004537A

Other languages

English (en)

Dutch (nl)

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.)

1979-08-17

Filing date

1980-08-08

Publication date

1981-02-19

1979-08-17 Priority claimed from CH756079A external-priority patent/CH644113A5/de

1980-08-08 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1981-02-19 Publication of NL8004537A publication Critical patent/NL8004537A/nl

Links

150000002391 heterocyclic compounds Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 49
150000003839 salts Chemical group 0.000 claims description 16
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
238000000034 method Methods 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 10
150000001204 N-oxides Chemical group 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 9
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
239000013543 active substance Substances 0.000 claims description 6
150000004965 peroxy acids Chemical class 0.000 claims description 5
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
235000019253 formic acid Nutrition 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
239000000825 pharmaceutical preparation Substances 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
241000222122 Candida albicans Species 0.000 claims description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
229940095731 candida albicans Drugs 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
208000015181 infectious disease Diseases 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
239000012876 carrier material Substances 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
230000003287 optical effect Effects 0.000 claims description 2
239000007787 solid Substances 0.000 claims description 2
230000001857 anti-mycotic effect Effects 0.000 claims 2
239000002543 antimycotic Substances 0.000 claims 2
231100000252 nontoxic Toxicity 0.000 claims 2
230000003000 nontoxic effect Effects 0.000 claims 2
239000000969 carrier Substances 0.000 claims 1
230000002538 fungal effect Effects 0.000 claims 1
244000053095 fungal pathogen Species 0.000 claims 1
239000007788 liquid Substances 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
230000001225 therapeutic effect Effects 0.000 claims 1
244000000190 yeast pathogen Species 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
239000003054 catalyst Substances 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 10
HNVIQLPOGUDBSU-OLQVQODUSA-N (2s,6r)-2,6-dimethylmorpholine Chemical compound C[C@H]1CNC[C@@H](C)O1 HNVIQLPOGUDBSU-OLQVQODUSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
239000007858 starting material Substances 0.000 description 8
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 7
229910052753 mercury Inorganic materials 0.000 description 7
239000002904 solvent Substances 0.000 description 7
MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
238000005984 hydrogenation reaction Methods 0.000 description 6
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
-1 carbonium ion Chemical class 0.000 description 5
238000001816 cooling Methods 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
241000233866 Fungi Species 0.000 description 4
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 description 4
230000000694 effects Effects 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
235000011121 sodium hydroxide Nutrition 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000222120 Candida <Saccharomycetales> Species 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
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 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
239000002585 base Substances 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000002674 ointment Substances 0.000 description 3
229910052697 platinum Inorganic materials 0.000 description 3
230000007017 scission Effects 0.000 description 3
239000011975 tartaric acid Substances 0.000 description 3
229960001367 tartaric acid Drugs 0.000 description 3
235000002906 tartaric acid Nutrition 0.000 description 3
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
238000005727 Friedel-Crafts reaction Methods 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
239000005662 Paraffin oil Substances 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229960004106 citric acid Drugs 0.000 description 2
150000002081 enamines Chemical class 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
230000000855 fungicidal effect Effects 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
239000001630 malic acid Substances 0.000 description 2
235000011090 malic acid Nutrition 0.000 description 2
238000002156 mixing Methods 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
235000019271 petrolatum Nutrition 0.000 description 2
230000003032 phytopathogenic effect Effects 0.000 description 2
229940072033 potash Drugs 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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238000006722 reduction reaction Methods 0.000 description 2
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235000019698 starch Nutrition 0.000 description 2
239000000126 substance Substances 0.000 description 2
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JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
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MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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RJOWHRLIQNKYKW-UHFFFAOYSA-N 2-methyl-2-phenylpropanal Chemical class O=CC(C)(C)C1=CC=CC=C1 RJOWHRLIQNKYKW-UHFFFAOYSA-N 0.000 description 1
VLUMOWNVWOXZAU-UHFFFAOYSA-N 2-methyl-3-phenylprop-2-enal Chemical compound O=CC(C)=CC1=CC=CC=C1 VLUMOWNVWOXZAU-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
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
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241001529717 Corticium <basidiomycota> Species 0.000 description 1
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150000001335 aliphatic alkanes Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
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229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
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239000011575 calcium Substances 0.000 description 1
235000001465 calcium Nutrition 0.000 description 1
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LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
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150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
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KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
229960002598 fumaric acid Drugs 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
230000001408 fungistatic effect Effects 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
235000013922 glutamic acid Nutrition 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
238000003898 horticulture Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
229960000448 lactic acid Drugs 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229940098895 maleic acid Drugs 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
239000007800 oxidant agent 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
230000003071 parasitic effect Effects 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
235000011118 potassium hydroxide Nutrition 0.000 description 1
239000010970 precious metal Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
210000005000 reproductive tract Anatomy 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
241000894007 species Species 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000003826 tablet 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
CRNIHJHMEQZAAS-UHFFFAOYSA-N tert-amyl chloride Chemical compound CCC(C)(C)Cl CRNIHJHMEQZAAS-UHFFFAOYSA-N 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
239000000003 vaginal tablet Substances 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
239000008096 xylene Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NL8004537A 1979-08-17 1980-08-08 Heterocyclische verbindingen. NL8004537A (nl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
CH756079		1979-08-17
CH756079A CH644113A5 (en)	1979-08-17	1979-08-17	N-substituted 2,6-dimethylmorpholine compounds
CH418780		1980-05-29
CH418780		1980-05-29

Publications (1)

Publication Number	Publication Date
NL8004537A true NL8004537A (nl)	1981-02-19

Family

ID=25694874

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8004537A NL8004537A (nl)	1979-08-17	1980-08-08	Heterocyclische verbindingen.

Country Status (31)

Country	Link
EP (1)	EP0024334B1 (fr)
AR (1)	AR225318A1 (fr)
AT (1)	ATE4206T1 (fr)
AU (1)	AU530398B2 (fr)
BG (1)	BG60798B2 (fr)
CA (1)	CA1128943A (fr)
CS (1)	CS402091A3 (fr)
CU (1)	CU35298A (fr)
DE (3)	DE19375077I2 (fr)
DK (1)	DK150509C (fr)
ES (2)	ES494314A0 (fr)
FI (1)	FI69455C (fr)
FR (1)	FR2463767B1 (fr)
GB (1)	GB2056454B (fr)
HR (1)	HRP930340B1 (fr)
HU (1)	HU182189B (fr)
IE (1)	IE52642B1 (fr)
IL (1)	IL60813A (fr)
IT (1)	IT1220970B (fr)
LU (1)	LU82713A1 (fr)
MC (1)	MC1345A1 (fr)
MY (1)	MY8500272A (fr)
NL (1)	NL8004537A (fr)
NO (1)	NO153176C (fr)
NZ (1)	NZ194628A (fr)
PH (1)	PH15480A (fr)
PT (1)	PT71708B (fr)
SE (1)	SE447730B (fr)
SI (1)	SI8011754A8 (fr)
YU (1)	YU43475B (fr)
ZW (1)	ZW15780A1 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3421810A1 (de) *	1984-06-12	1985-12-12	Basf Ag, 6700 Ludwigshafen	Phenylalkylamine - bioregulatoren
CA2008775C (fr) *	1989-02-24	1998-12-22	Alberto Ferro	Vernis a ongles
EP0446585A1 (fr) *	1990-03-12	1991-09-18	F. Hoffmann-La Roche Ag	Procédé de lutte contre les infections fongiques en aquaculture
EP1749826A1 (fr)	2005-07-28	2007-02-07	Galderma S.A.	Procédé pour al préparation de bépromoline
EP1749825A1 (fr) *	2005-07-28	2007-02-07	Galderma S.A.	Procédé pour la préparation d' amorolfine
EP1842848A1 (fr) *	2006-04-03	2007-10-10	Galderma S.A.	Procédé de préparation de 3-[4-(1,1-diméthyl-propyl)-phényl]-2-méthyl-propionaldéhyde et de cis-4{3-[4-(1,1-diméthyl-propyl)-phényl] 2-méthyl-propyl}-2,6-diméthyl-morpholine (amorolfine)
EP1935889A1 (fr) *	2006-12-21	2008-06-25	Galderma S.A.	Procédé de production d'amorolfine
ITFI20090032A1 (it)	2009-02-20	2010-08-21	Synteco S P A Prodotti Di Sintesi Per L Ind	Processo di produzione industriale dell'amorolfina cloridrato

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT354187B (de) *	1976-11-22	1979-12-27	Hoffmann La Roche	Fungizides mittel
DE2656747C2 (de) *	1976-12-15	1984-07-05	Basf Ag, 6700 Ludwigshafen	Morpholinderivate
ZA792242B (en) *	1978-05-16	1980-05-28	Hoffmann La Roche	Heterocyclic compounds
DE2830127A1 (de) *	1978-07-08	1980-01-17	Basf Ag	N-arylpropyl-substituierte cyclische amine
DE2830999A1 (de) *	1978-07-14	1980-01-31	Basf Ag	Verfahren zur herstellung von stereoisomeren n-aralkyl-2,6-dimethylmorpholinen
ATE3111T1 (de) *	1978-08-08	1983-05-15	F. Hoffmann-La Roche & Co. Aktiengesellschaft	Verfahren zur herstellung von phenyl-propylmorpholin- und -piperidin-derivaten.
DE2907614A1 (de) *	1979-02-27	1980-09-04	Basf Ag	Optische aktive formen des 1- eckige klammer auf 3-(p-tert.-buthylphenyl)-2- methylpropyl eckige klammer zu -cis-3,5- dimethylmorpholins

1980
- 1980-07-07 ZW ZW157/80A patent/ZW15780A1/xx unknown
- 1980-07-07 IT IT23283/80A patent/IT1220970B/it active
- 1980-07-08 SI SI8011754A patent/SI8011754A8/sl unknown
- 1980-07-08 YU YU1754/80A patent/YU43475B/xx unknown
- 1980-07-11 CA CA356,038A patent/CA1128943A/fr not_active Expired
- 1980-07-25 AR AR281915A patent/AR225318A1/es active
- 1980-07-30 CU CU8035298A patent/CU35298A/es unknown
- 1980-08-01 FI FI802418A patent/FI69455C/fi not_active IP Right Cessation
- 1980-08-05 PH PH24406A patent/PH15480A/en unknown
- 1980-08-07 DE DE1993175077 patent/DE19375077I2/de active Active
- 1980-08-07 DE DE19803029966 patent/DE3029966A1/de not_active Withdrawn
- 1980-08-07 EP EP80104656A patent/EP0024334B1/fr not_active Expired
- 1980-08-07 DE DE8080104656T patent/DE3064267D1/de not_active Expired
- 1980-08-07 AT AT80104656T patent/ATE4206T1/de active
- 1980-08-08 NL NL8004537A patent/NL8004537A/nl not_active Application Discontinuation
- 1980-08-11 NZ NZ194628A patent/NZ194628A/en unknown
- 1980-08-11 IL IL60813A patent/IL60813A/xx unknown
- 1980-08-11 AU AU61321/80A patent/AU530398B2/en not_active Expired
- 1980-08-14 MC MC801466A patent/MC1345A1/fr unknown
- 1980-08-14 PT PT71708A patent/PT71708B/pt unknown
- 1980-08-14 LU LU82713A patent/LU82713A1/de unknown
- 1980-08-14 FR FR8017977A patent/FR2463767B1/fr not_active Expired
- 1980-08-15 SE SE8005784A patent/SE447730B/sv not_active IP Right Cessation
- 1980-08-15 HU HU802034A patent/HU182189B/hu unknown
- 1980-08-15 DK DK355180A patent/DK150509C/da not_active IP Right Cessation
- 1980-08-15 NO NO802453A patent/NO153176C/no unknown
- 1980-08-15 GB GB8026709A patent/GB2056454B/en not_active Expired
- 1980-08-15 IE IE1729/80A patent/IE52642B1/en not_active IP Right Cessation
- 1980-08-16 ES ES494314A patent/ES494314A0/es active Granted
1981
- 1981-03-02 ES ES499957A patent/ES8201563A1/es not_active Expired
1985
- 1985-12-30 MY MY272/85A patent/MY8500272A/xx unknown
1991
- 1991-12-23 CS CS914020A patent/CS402091A3/cs unknown
1993
- 1993-03-12 HR HRP-1754/80A patent/HRP930340B1/xx not_active IP Right Cessation
1994
- 1994-02-25 BG BG098580A patent/BG60798B2/bg unknown

Also Published As

Publication number	Publication date
YU43475B (en)	1989-08-31
BG60798B2 (bg)	1996-03-29
IT8023283A0 (it)	1980-07-07
NO153176B (no)	1985-10-21
FI802418A7 (fi)	1981-02-18
HU182189B (en)	1983-12-28
IT1220970B (it)	1990-06-21
IL60813A0 (en)	1980-10-26
DK150509B (da)	1987-03-16
CA1128943A (fr)	1982-08-03
AR225318A1 (es)	1982-03-15
PT71708B (en)	1982-04-06
IE801729L (en)	1981-02-17
CU35298A (en)	1982-03-28
ES8200355A1 (es)	1981-11-01
FI69455C (fi)	1986-02-10
CS402091A3 (en)	1992-05-13
MY8500272A (en)	1985-12-31
IL60813A (en)	1984-06-29
AU6132180A (en)	1981-02-19
ATE4206T1 (de)	1983-08-15
DE3029966A1 (de)	1981-03-26
NO802453L (no)	1981-02-18
FR2463767A1 (fr)	1981-02-27
EP0024334A1 (fr)	1981-03-04
IE52642B1 (en)	1988-01-06
SI8011754A8 (sl)	1997-06-30
YU175480A (en)	1983-02-28
ES499957A0 (es)	1982-01-01
LU82713A1 (de)	1982-05-10
FI69455B (fi)	1985-10-31
SE8005784L (sv)	1981-02-18
PT71708A (en)	1980-10-01
FR2463767B1 (fr)	1985-07-12
PH15480A (en)	1983-01-27
GB2056454B (en)	1983-11-09
GB2056454A (en)	1981-03-18
DE3064267D1 (en)	1983-08-25
NO153176C (no)	1986-01-29
ES494314A0 (es)	1981-11-01
MC1345A1 (fr)	1981-06-22
SE447730B (sv)	1986-12-08
DE19375077I2 (de)	2001-04-12
EP0024334B1 (fr)	1983-07-20
NZ194628A (en)	1984-09-28
HRP930340B1 (en)	1996-12-31
ES8201563A1 (es)	1982-01-01
AU530398B2 (en)	1983-07-14
ZW15780A1 (en)	1981-03-18
DK150509C (da)	1987-10-12
DK355180A (da)	1981-02-18

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1987-10-01	BV	The patent application has lapsed

Publication	Publication Date	Title
CA1107282A (fr)	1981-08-18	Procede d'obtention de derives morpholine et de piperidine et produits qui en derivent
EP0041673B1 (fr)	1984-10-10	Dérivés d'imidazole, leur préparation et compositions les contenant
US3293263A (en)	1966-12-20	Diphenylbenzocycloalkenes
EP0331983B1 (fr)	1994-12-14	Dérivés du stilbène, leur préparation et leur utilisation dans les médicaments
EP0054974A1 (fr)	1982-06-30	Dérivés de l'imidazolylpropanole et leurs sels d'addition avec un acide, procédé de préparation et leur utilisation
US3682951A (en)	1972-08-08	1-{8 {62 -(1-adamantyloxy)halophenethyl{9 {0 imidazoles and congeners
NL8004537A (nl)	1981-02-19	Heterocyclische verbindingen.
US4017631A (en)	1977-04-12	Imidazolium salts
US4216326A (en)	1980-08-05	Intermediates for preparing anti-inflammatory phenyl-lower-alkylamines
US4740601A (en)	1988-04-26	Imidazole derivatives having antimicrobial activities
EP0005541A2 (fr)	1979-11-28	Dérivés substitués de pipéridine, de morpholine ou de pipéridone, fongicides contenant ces composés, procédé pour leur préparation et pour leur utilisation, et l'utilisation de ces composés comme fongicides
DE3042844A1 (de)	1981-05-27	2-(1h-imidazol-1-yl)-aethoxyderivate von chinolin-2- und 4-methanolen, verfahren zu ihrer herstellung, arzneimittel und ihre verwendung
US5110826A (en)	1992-05-05	Azole derivatives and antifungal drugs containing the same as an active component
DE3876546T2 (de)	1993-04-15	Ethanon-oxime.
JPH0248553B2 (fr)	1990-10-25
EP0392326B1 (fr)	1994-07-20	Dérivés d'imidazolo dichloro substitués comme agents fongicides
JPH0454668B2 (fr)	1992-08-31
CH650502A5 (de)	1985-07-31	1-phenaethylimidazol-derivate.
DD278591A5 (de)	1990-05-09	Verfahren zur herstellung neuer azolylmethylsilane
US4451655A (en)	1984-05-29	Process for preparing carboline derivatives and compounds used in their preparation
US3991075A (en)	1976-11-09	1-[3-(4-Hydroxybenzylamino)propyl]pyrrolidine dihydrobromide and intermediate therefor