CH644113A5 - N-substituted 2,6-dimethylmorpholine compounds - Google Patents
N-substituted 2,6-dimethylmorpholine compounds Download PDFInfo
- Publication number
- CH644113A5 CH644113A5 CH756079A CH756079A CH644113A5 CH 644113 A5 CH644113 A5 CH 644113A5 CH 756079 A CH756079 A CH 756079A CH 756079 A CH756079 A CH 756079A CH 644113 A5 CH644113 A5 CH 644113A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- compounds
- acid
- salts
- preparation
- Prior art date
Links
- -1 N-substituted 2,6-dimethylmorpholine compounds Chemical class 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 8
- 150000004965 peroxy acids Chemical class 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- HNVIQLPOGUDBSU-OLQVQODUSA-N (2s,6r)-2,6-dimethylmorpholine Chemical compound C[C@H]1CNC[C@@H](C)O1 HNVIQLPOGUDBSU-OLQVQODUSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000012876 carrier material Substances 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical class O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 claims description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 229940117916 cinnamic aldehyde Drugs 0.000 claims description 2
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000417 fungicide Substances 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 241000222122 Candida albicans Species 0.000 abstract description 3
- 229940095731 candida albicans Drugs 0.000 abstract description 3
- 230000000855 fungicidal effect Effects 0.000 abstract description 3
- 230000001857 anti-mycotic effect Effects 0.000 abstract 1
- 239000002543 antimycotic Substances 0.000 abstract 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 241000221785 Erysiphales Species 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
- 235000013339 cereals Nutrition 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-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
- 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
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- 150000007513 acids Chemical class 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 235000019271 petrolatum Nutrition 0.000 description 3
- 230000007017 scission Effects 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
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-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
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 244000141359 Malus pumila Species 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
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000221300 Puccinia Species 0.000 description 2
- 241000220317 Rosa Species 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 241000589634 Xanthomonas Species 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 208000015181 infectious disease Diseases 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
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 230000003032 phytopathogenic effect Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-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
- 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
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241001480061 Blumeria graminis Species 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 241001600093 Coniophora Species 0.000 description 1
- 241001529717 Corticium <basidiomycota> Species 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 241000371644 Curvularia ravenelii Species 0.000 description 1
- 241000588698 Erwinia Species 0.000 description 1
- 241000922683 Erwinia tracheiphila Species 0.000 description 1
- 208000014770 Foot disease Diseases 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 241001149475 Gaeumannomyces graminis Species 0.000 description 1
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 1
- 241001181537 Hemileia Species 0.000 description 1
- 241001181532 Hemileia vastatrix Species 0.000 description 1
- 241000228402 Histoplasma Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000001358 L(+)-tartaric acid Substances 0.000 description 1
- 235000011002 L(+)-tartaric acid Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 241000222634 Lenzites Species 0.000 description 1
- 241001661267 Marssonina rosae Species 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000896238 Oidium Species 0.000 description 1
- 241000736122 Parastagonospora nodorum Species 0.000 description 1
- 241000315044 Passalora arachidicola Species 0.000 description 1
- 241001223281 Peronospora Species 0.000 description 1
- 241000499488 Phragmidium mucronatum Species 0.000 description 1
- 241001337928 Podosphaera leucotricha Species 0.000 description 1
- 241000896203 Podosphaera pannosa Species 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241001123561 Puccinia coronata Species 0.000 description 1
- 241000221301 Puccinia graminis Species 0.000 description 1
- 241001123569 Puccinia recondita Species 0.000 description 1
- 241001123567 Puccinia sorghi Species 0.000 description 1
- 241001361634 Rhizoctonia Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 241000865903 Thielaviopsis Species 0.000 description 1
- 241000722133 Tilletia Species 0.000 description 1
- 241000221576 Uromyces Species 0.000 description 1
- 241000514371 Ustilago avenae Species 0.000 description 1
- 206010046914 Vaginal infection Diseases 0.000 description 1
- 201000008100 Vaginitis Diseases 0.000 description 1
- 241000228452 Venturia inaequalis Species 0.000 description 1
- 201000007096 Vulvovaginal Candidiasis Diseases 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 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
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000006071 cream 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
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 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
- AUONNNVJUCSETH-UHFFFAOYSA-N icosanoyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCCCC AUONNNVJUCSETH-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 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
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- NRZWYNLTFLDQQX-UHFFFAOYSA-N p-tert-Amylphenol Chemical compound CCC(C)(C)C1=CC=C(O)C=C1 NRZWYNLTFLDQQX-UHFFFAOYSA-N 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
- 235000020232 peanut Nutrition 0.000 description 1
- 150000002978 peroxides Chemical class 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
- 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
- 238000001953 recrystallisation Methods 0.000 description 1
- 210000005000 reproductive tract Anatomy 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000004071 soot Substances 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
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 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
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000000003 vaginal tablet Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Extraction Or Liquid Replacement (AREA)
Priority Applications (47)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH756079A CH644113A5 (en) | 1979-08-17 | 1979-08-17 | N-substituted 2,6-dimethylmorpholine compounds |
| ZW157/80A ZW15780A1 (en) | 1979-08-17 | 1980-07-07 | Heterocyclic compounds |
| IT23283/80A IT1220970B (it) | 1979-08-17 | 1980-07-07 | Composti eteterociclici ad azione fungicida particolare per la lotta contro la candida albicans |
| YU1754/80A YU43475B (en) | 1979-08-17 | 1980-07-08 | Process for producing morpholine derivatives |
| SI8011754A SI8011754A8 (sl) | 1979-08-17 | 1980-07-08 | Postopek za proizvodnjo derivatov morfolina |
| CA356,038A CA1128943A (en) | 1979-08-17 | 1980-07-11 | Morpholine derivatives |
| AR281915A AR225318A1 (es) | 1979-08-17 | 1980-07-25 | Procedimiento para preparar fenil-propil-morfolinas sustituidas |
| BR8004705A BR8004705A (pt) | 1979-08-17 | 1980-07-28 | Compostos heterociclicos, processo para manufactura de tais compostos, preparacao farmaceutica e uso dos compostos |
| CS816797A CS227329B2 (cs) | 1979-08-17 | 1980-07-29 | Způsob výroby derivátů morfolinu |
| CS805307A CS227310B2 (en) | 1979-08-17 | 1980-07-29 | Method of preparing morpholine derivatives |
| CU8035298A CU35298A (en) | 1979-08-17 | 1980-07-30 | Heterocyclic compounds |
| FI802418A FI69455C (fi) | 1979-08-17 | 1980-08-01 | Foerfarande foer framstaellning av cis-2,6-dimetylmorfolinderivat med fungicid verkan |
| PH24406A PH15480A (en) | 1979-08-17 | 1980-08-05 | Heterocyclic compounds |
| DE1993175077 DE19375077I2 (de) | 1979-08-17 | 1980-08-07 | Neue Morpholinderivate Verfahren zu deren Herstellung diese Derivate enthaltende pharmazeutische Praeparate |
| DE8080104656T DE3064267D1 (en) | 1979-08-17 | 1980-08-07 | Morpholine derivatives, process for their production, pharmaceutical preparations containing these derivatives |
| AT80104656T ATE4206T1 (de) | 1979-08-17 | 1980-08-07 | Neue morpholinderivate, verfahren zu deren herstellung, diese derivate enthaltende pharmazeutische praeparate. |
| DE19803029966 DE3029966A1 (de) | 1979-08-17 | 1980-08-07 | Heterocyclische verbindungen |
| EP80104656A EP0024334B1 (de) | 1979-08-17 | 1980-08-07 | Neue Morpholinderivate, Verfahren zu deren Herstellung, diese Derivate enthaltende pharmazeutische Präparate |
| NL8004537A NL8004537A (nl) | 1979-08-17 | 1980-08-08 | Heterocyclische verbindingen. |
| ZA00804866A ZA804866B (en) | 1979-08-17 | 1980-08-11 | Heterocyclic compounds |
| AU61321/80A AU530398B2 (en) | 1979-08-17 | 1980-08-11 | N-substituted-2,6-dimethylmorpholine derivatives |
| IL60813A IL60813A (en) | 1979-08-17 | 1980-08-11 | Cis-4-(3-p-(tert-amyl-phenyl and alpha,alpha-dimethyl-benzyl-phenyl)-2-methylpropyl)-2,6-dimethyl-morpholines,their preparation and pharmaceutical compositions containing them |
| NZ194628A NZ194628A (en) | 1979-08-17 | 1980-08-11 | Cis-4-(3-p-(tert-amyl or alpha,alpha-dimethylbenzyl)phenyl-2-methylpropyl)-2,6-dimethylmorpholines |
| MC801466A MC1345A1 (fr) | 1979-08-17 | 1980-08-14 | Procede pour la preparation de composes heterocycliques |
| FR8017977A FR2463767B1 (fr) | 1979-08-17 | 1980-08-14 | Nouveaux derives de cis-4-(3-phenyl-2-methyl-propyl)-2,6-dimethyl-morpholine, leur procede de preparation et medicaments les contenant |
| PT71708A PT71708B (en) | 1979-08-17 | 1980-08-14 | Process for preparing phenyl-propyl-morpholinic substituted compounds |
| GR62680A GR69944B (enrdf_load_stackoverflow) | 1979-08-17 | 1980-08-14 | |
| LU82713A LU82713A1 (de) | 1979-08-17 | 1980-08-14 | Heterocyclische verbindungen |
| JP11185280A JPS5677269A (en) | 1979-08-17 | 1980-08-15 | Heterocyclic compound |
| IE1729/80A IE52642B1 (en) | 1979-08-17 | 1980-08-15 | Morpholine derivatives,process for preparing them and use of said morpholine derivatives in pharmaceutical preparations |
| NO802453A NO153176C (no) | 1979-08-17 | 1980-08-15 | Analogifremgangsmaate ved fremstilling av den terapeutisk virksomme cis-isomer av morfolinderivater. |
| GB8026709A GB2056454B (en) | 1979-08-17 | 1980-08-15 | 2,6 - dimethyl morpholine derivatives |
| DK355180A DK150509C (da) | 1979-08-17 | 1980-08-15 | Analogifremgangsmaade til fremstilling af cis-4-(3-phenyl-2-methyl-propyl)-2,6-dimethylmorpholiner |
| HU802034A HU182189B (en) | 1979-08-17 | 1980-08-15 | Process for preparing morpholine compounds |
| SE8005784A SE447730B (sv) | 1979-08-17 | 1980-08-15 | Morfolinderivat, forfarande for framstellning derav samt farmaceutiska preparat innehallande sadana foreningar till anvendning som antimykotika |
| ES494314A ES8200355A1 (es) | 1979-08-17 | 1980-08-16 | Un procedimiento para la preparacion de compuestos heteroci-clicos |
| KR1019800003239A KR840001472B1 (ko) | 1979-08-17 | 1980-08-16 | 모르폴린 유도체의 제조방법 |
| ES499957A ES8201563A1 (es) | 1979-08-17 | 1981-03-02 | Un procedimiento para la preparacion de compuestos heteroci-clicos |
| ES499956A ES8201562A1 (es) | 1979-08-17 | 1981-03-02 | Un procedimiento para la preparacion de compuestos heteroci-clicos |
| ES499955A ES8201561A1 (es) | 1979-08-17 | 1981-03-02 | Un procedimiento para la preparacion de compuestos heteroci-clicos |
| CS816796A CS227328B2 (cs) | 1979-08-17 | 1981-09-15 | Způsob výroby derivátů morfolinu |
| MY272/85A MY8500272A (en) | 1979-08-17 | 1985-12-30 | Substituted-phenyl propyl morpholines |
| CS914020A CS402091A3 (en) | 1979-08-17 | 1991-12-23 | Morpholine derivatives and pharmaceuticals based thereon |
| MX9203269A MX9203269A (es) | 1979-08-17 | 1992-06-24 | Compuestos heterociclicos y composiciones farmaceuticas que los contienen. |
| HRP-1754/80A HRP930340B1 (en) | 1979-08-17 | 1993-03-12 | Process for the preparation of morpholine derivatives |
| BG098580A BG60798B2 (bg) | 1979-08-17 | 1994-02-25 | Нови морфолинови производни,метод за тяхното получаване, фармацевтични средства,съдържащи тези производни,и използването им като антимикотици |
| NO1994009C NO1994009I1 (no) | 1979-08-17 | 1994-08-03 | Amorolfin/ cis-4-(3-(4-(1,1-dimetylpropyl)-fenyl)-2-metylpropyl-2,6-dimetylmorfolin. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH756079A CH644113A5 (en) | 1979-08-17 | 1979-08-17 | N-substituted 2,6-dimethylmorpholine compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH644113A5 true CH644113A5 (en) | 1984-07-13 |
Family
ID=4327075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH756079A CH644113A5 (en) | 1979-08-17 | 1979-08-17 | N-substituted 2,6-dimethylmorpholine compounds |
Country Status (10)
Family Cites Families (3)
| 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 |
| JPS6236516A (ja) * | 1985-08-12 | 1987-02-17 | Matsushita Electric Ind Co Ltd | 角速度センサ |
-
1979
- 1979-08-17 CH CH756079A patent/CH644113A5/de not_active IP Right Cessation
-
1980
- 1980-07-28 BR BR8004705A patent/BR8004705A/pt unknown
- 1980-07-29 CS CS816797A patent/CS227329B2/cs unknown
- 1980-07-29 CS CS805307A patent/CS227310B2/cs unknown
- 1980-08-11 ZA ZA00804866A patent/ZA804866B/xx unknown
- 1980-08-14 GR GR62680A patent/GR69944B/el unknown
- 1980-08-15 JP JP11185280A patent/JPS5677269A/ja active Granted
- 1980-08-16 KR KR1019800003239A patent/KR840001472B1/ko not_active Expired
-
1981
- 1981-03-02 ES ES499955A patent/ES8201561A1/es not_active Expired
- 1981-03-02 ES ES499956A patent/ES8201562A1/es not_active Expired
- 1981-09-15 CS CS816796A patent/CS227328B2/cs unknown
-
1992
- 1992-06-24 MX MX9203269A patent/MX9203269A/es unknown
-
1994
- 1994-08-03 NO NO1994009C patent/NO1994009I1/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5677269A (en) | 1981-06-25 |
| MX9203269A (es) | 1992-07-01 |
| ES499956A0 (es) | 1982-01-01 |
| ES499955A0 (es) | 1982-01-01 |
| BR8004705A (pt) | 1981-04-28 |
| CS227329B2 (cs) | 1984-04-16 |
| CS227328B2 (cs) | 1984-04-16 |
| ES8201562A1 (es) | 1982-01-01 |
| ES8201561A1 (es) | 1982-01-01 |
| KR830003448A (ko) | 1983-06-20 |
| JPH0248553B2 (enrdf_load_stackoverflow) | 1990-10-25 |
| KR840001472B1 (ko) | 1984-09-28 |
| GR69944B (enrdf_load_stackoverflow) | 1982-07-21 |
| NO1994009I1 (no) | 1994-08-03 |
| CS227310B2 (en) | 1984-04-16 |
| ZA804866B (en) | 1981-08-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1940388C3 (de) | l-(ß-Aryl) äthylimidazolderivate, ihre Herstellung und diese enthaltende fungizide und bakterizide Mittel | |
| DE2752135C2 (de) | Heterocyclische Verbindungen | |
| DE2037610C3 (enrdf_load_stackoverflow) | ||
| DE19681478B4 (de) | R-(-)-(E)-[4-(2,4-Dichlorphenyl)-1,3-dithiolan-2-yliden]-1-imidazolylacetonitril,Verfahren zu seiner Herstellung und seine Verwendung | |
| DE2041771C3 (de) | derivate | |
| EP0041673B1 (de) | Imidazolderivate, deren Herstellung sowie diese enthaltende Präparate | |
| DE2333354A1 (de) | Imidazolyl-o,n-acetale sowie deren salze, verfahren zu ihrer herstellung und ihre verwendung als fungizide | |
| DE2350122C2 (de) | 1-Propyl-1,2,4-triazolyl-Derivate und deren Salze, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide | |
| DE2633492C2 (enrdf_load_stackoverflow) | ||
| EP0024334B1 (de) | Neue Morpholinderivate, Verfahren zu deren Herstellung, diese Derivate enthaltende pharmazeutische Präparate | |
| DE3010093A1 (de) | 1,1-diphenyl-2-(1.2.4-triazol-1-yl)-aethan-1-ole, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel | |
| EP0005541A2 (de) | Substituierte Piperidin-, Morpholin- oder Piperidonderivate, fungizide Mittel, die diese Verbindungen enthalten, Verfahren zu deren Herstellung und Verwendung sowie die Verwendung dieser Verbindungen als Fungizide | |
| EP0129211B1 (de) | 2,6-Trans-Dimethylmorpholinderivate und diese enthaltende Fungizide und Verfahren zur Bekämpfung von Pilzen | |
| EP0083750B1 (de) | Antimykotische Azolyl-butanole | |
| CH644113A5 (en) | N-substituted 2,6-dimethylmorpholine compounds | |
| EP0002671A1 (de) | Substituierte Triazolylglykoläther, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide | |
| DE2541833C2 (enrdf_load_stackoverflow) | ||
| EP0033501A2 (de) | Beta-Imidazolylalkohole, Verfahren zu ihrer Herstellung, diese enthaltende Fungizide und Verfahren zur Bekämpfung von Pilzen mit ihnen | |
| DE2429514A1 (de) | Eckige klammer auf 1-imidazolyl-(1) eckige klammer zu- eckige klammer auf 1-(4'-(4''-chlorphenyl)-phenoxy eckige klammer zu-3,3-dimethyl-butan-2-on und seine salze, ein verfahren zu ihrer herstellung als arzneimittel | |
| DE3617190A1 (de) | Neue azolderivate, verfahren zu ihrer herstellung und ihre verwendung | |
| EP0041615B1 (de) | Verwendung von Imidazolyl-vinyl-ketonen und-carbinolen als antimikrobielle Mittel | |
| DE3732910A1 (de) | Fungizide n-substituierte 3-alkyl-4-aryl-pyrrolidin-derivate | |
| EP0033088B1 (de) | Antimykotische Mittel | |
| DE3630193A1 (de) | Triazolylmetallkomplexe | |
| CH633185A5 (en) | Antimycotic agent |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |