CS236796B2 - Processing of 3-(3-(trifluormethyl)fenoxy)-1-azeidin -carboxamide - Google Patents
Processing of 3-(3-(trifluormethyl)fenoxy)-1-azeidin -carboxamide Download PDFInfo
- Publication number
- CS236796B2 CS236796B2 CS835172A CS517283A CS236796B2 CS 236796 B2 CS236796 B2 CS 236796B2 CS 835172 A CS835172 A CS 835172A CS 517283 A CS517283 A CS 517283A CS 236796 B2 CS236796 B2 CS 236796B2
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- CS
- Czechoslovakia
- Prior art keywords
- preparation
- phenoxy
- compounds
- formula
- mixture
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 41
- 238000002360 preparation method Methods 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 22
- CMUOJBJRZUHRMU-UHFFFAOYSA-N nitrourea Chemical compound NC(=O)N[N+]([O-])=O CMUOJBJRZUHRMU-UHFFFAOYSA-N 0.000 claims description 5
- LIAILJLSVRAGSM-UHFFFAOYSA-N dezinamide Chemical compound C1N(C(=O)N)CC1OC1=CC=CC(C(F)(F)F)=C1 LIAILJLSVRAGSM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 17
- 230000001773 anti-convulsant effect Effects 0.000 abstract description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 9
- 239000001961 anticonvulsive agent Substances 0.000 abstract description 8
- 229960003965 antiepileptics Drugs 0.000 abstract description 7
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- 239000001257 hydrogen Substances 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 3
- XQHOIPJEWVQKGA-UHFFFAOYSA-N 3-phenoxyazetidine-1-carboxamide Chemical class C1N(C(=O)N)CC1OC1=CC=CC=C1 XQHOIPJEWVQKGA-UHFFFAOYSA-N 0.000 abstract description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 230000002035 prolonged effect Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
- 239000000203 mixture Substances 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- -1 α-methylbenzyl Chemical group 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 13
- 235000019441 ethanol Nutrition 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 241000699670 Mus sp. Species 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 229920000609 methyl cellulose Polymers 0.000 description 9
- 239000001923 methylcellulose Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000002775 capsule Substances 0.000 description 8
- 150000003857 carboxamides Chemical class 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
- 206010010904 Convulsion Diseases 0.000 description 6
- 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 6
- 241000699666 Mus <mouse, genus> Species 0.000 description 6
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 206010015037 epilepsy Diseases 0.000 description 6
- 239000008101 lactose Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000008107 starch Substances 0.000 description 6
- 235000019698 starch Nutrition 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
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- 239000008187 granular material Substances 0.000 description 5
- 238000007327 hydrogenolysis reaction Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 206010021118 Hypotonia Diseases 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 4
- 208000028329 epileptic seizure Diseases 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 230000036640 muscle relaxation Effects 0.000 description 4
- 239000003158 myorelaxant agent Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 3
- 235000013539 calcium stearate Nutrition 0.000 description 3
- 239000008116 calcium stearate Substances 0.000 description 3
- 125000005518 carboxamido group Chemical group 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 229940099112 cornstarch Drugs 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YNDQPJIQUZYADI-BTJKTKAUSA-N (z)-but-2-enedioic acid;1-(1-phenylethyl)azetidin-3-ol Chemical compound OC(=O)\C=C/C(O)=O.C=1C=CC=CC=1C(C)N1CC(O)C1 YNDQPJIQUZYADI-BTJKTKAUSA-N 0.000 description 2
- GLAMCKIBNCIMFW-UHFFFAOYSA-N 1-benzhydryl-3-phenoxyazetidine Chemical compound C1C(OC=2C=CC=CC=2)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 GLAMCKIBNCIMFW-UHFFFAOYSA-N 0.000 description 2
- RZMGMNVKDONYNL-UHFFFAOYSA-N C(C(=O)O)(=O)O.N1CCC1 Chemical compound C(C(=O)O)(=O)O.N1CCC1 RZMGMNVKDONYNL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 240000006394 Sorghum bicolor Species 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000007928 intraperitoneal injection Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 230000003387 muscular Effects 0.000 description 2
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000003313 weakening effect Effects 0.000 description 2
- UNNNAIWPDLRVRN-UHFFFAOYSA-N 1-fluoro-4-(trifluoromethyl)benzene Chemical compound FC1=CC=C(C(F)(F)F)C=C1 UNNNAIWPDLRVRN-UHFFFAOYSA-N 0.000 description 1
- TWYHCXNPOTXNJF-UHFFFAOYSA-N 1-phenoxyazetidine Chemical compound C1CCN1OC1=CC=CC=C1 TWYHCXNPOTXNJF-UHFFFAOYSA-N 0.000 description 1
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 description 1
- CCXGQYXFUVSJEW-UHFFFAOYSA-N 3-(azetidin-3-yloxy)benzamide Chemical compound NC(=O)C1=CC=CC(OC2CNC2)=C1 CCXGQYXFUVSJEW-UHFFFAOYSA-N 0.000 description 1
- RKANEZKQFZAZHZ-UHFFFAOYSA-N 3-[4-(trifluoromethyl)phenoxy]azetidine Chemical compound C1=CC(C(F)(F)F)=CC=C1OC1CNC1 RKANEZKQFZAZHZ-UHFFFAOYSA-N 0.000 description 1
- MHCRLDZZHOVFEE-UHFFFAOYSA-N 4-(4-aminophenyl)morpholin-3-one Chemical compound C1=CC(N)=CC=C1N1C(=O)COCC1 MHCRLDZZHOVFEE-UHFFFAOYSA-N 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 206010009346 Clonus Diseases 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- UOWHCAKKYIRMSX-UHFFFAOYSA-N [N].C1CNC1 Chemical group [N].C1CNC1 UOWHCAKKYIRMSX-UHFFFAOYSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 229960000383 azatadine Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
- 239000007963 capsule composition Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000019700 dicalcium phosphate Nutrition 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
- KKNKTXBMIQSTCK-UHFFFAOYSA-N ethyl 4-[3-hydroxy-6,6-dimethyl-2,4-dioxo-3-(trifluoromethyl)-5,7-dihydroindol-1-yl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N1C(CC(C)(C)CC2=O)=C2C(O)(C(F)(F)F)C1=O KKNKTXBMIQSTCK-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 150000008423 fluorobenzenes Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000004615 ingredient Substances 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
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- PZSYSFIBRGYUSH-UHFFFAOYSA-N methanesulfonic acid;3-phenoxyazetidine Chemical compound CS(O)(=O)=O.C1NCC1OC1=CC=CC=C1 PZSYSFIBRGYUSH-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- ZBUPTTNVSQUORY-UHFFFAOYSA-N oxalic acid;3-[1-(1-phenylethyl)azetidin-3-yl]oxybenzamide Chemical compound OC(=O)C(O)=O.C=1C=CC=CC=1C(C)N(C1)CC1OC1=CC=CC(C(N)=O)=C1 ZBUPTTNVSQUORY-UHFFFAOYSA-N 0.000 description 1
- WEOSEWRUCNPFCW-UHFFFAOYSA-N oxalic acid;3-[4-(trifluoromethyl)phenoxy]azetidine Chemical compound OC(=O)C(O)=O.C1=CC(C(F)(F)F)=CC=C1OC1CNC1 WEOSEWRUCNPFCW-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000007916 tablet composition Substances 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960001005 tuberculin Drugs 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40947682A | 1982-08-19 | 1982-08-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS236796B2 true CS236796B2 (en) | 1985-05-15 |
Family
ID=23620657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS835172A CS236796B2 (en) | 1982-08-19 | 1983-07-07 | Processing of 3-(3-(trifluormethyl)fenoxy)-1-azeidin -carboxamide |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP0102194B1 (h) |
| JP (1) | JPH0643388B2 (h) |
| KR (1) | KR900001210B1 (h) |
| AU (1) | AU553528B2 (h) |
| CA (1) | CA1173841A (h) |
| CS (1) | CS236796B2 (h) |
| DE (1) | DE3367089D1 (h) |
| DK (1) | DK165741C (h) |
| EG (1) | EG16472A (h) |
| ES (1) | ES8500225A1 (h) |
| FI (1) | FI77225C (h) |
| GR (1) | GR79634B (h) |
| HK (1) | HK47487A (h) |
| HU (1) | HU190608B (h) |
| IE (1) | IE55769B1 (h) |
| IL (1) | IL68699A (h) |
| IN (1) | IN157045B (h) |
| MX (1) | MX9203639A (h) |
| NO (1) | NO157976C (h) |
| NZ (1) | NZ205317A (h) |
| PH (1) | PH19595A (h) |
| PL (1) | PL140765B1 (h) |
| PT (1) | PT77217B (h) |
| YU (1) | YU44854B (h) |
| ZA (1) | ZA834371B (h) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4594189A (en) * | 1983-07-06 | 1986-06-10 | A. H. Robins Company, Inc. | Process for preparing 3-phenoxy-1-azetidines and carboxamide derivatives |
| US4956359A (en) * | 1985-02-28 | 1990-09-11 | A. H. Robins Company, Inc. | 3-aryloxy and 3-arylthioazetidinecarboxamides as anticonvulsants and antiepileptics |
| FI87559C (fi) * | 1985-02-28 | 1993-01-25 | Robins Co Inc A H | Foerfarande foer framstaellning av aktiva 3-fenyloxiazetidinkarboxamider |
| US5183902A (en) * | 1985-02-28 | 1993-02-02 | A. H. Robins Company, Incorporated | Method of treating muscular tension, muscle spasticity and anxiety with 3-aryloxy and 3-arylthioazetidinecarboxamides |
| ZA861210B (en) * | 1985-02-28 | 1987-10-28 | Robins Co Inc A H | 3-aryloxyazetidinecarboxamides as anticonvulsants and antiepileptics |
| US5068231A (en) * | 1985-02-28 | 1991-11-26 | A. H. Robins Company Incorporated | Method of treating muscular tension, muscle spasticity and anxiety with 3-aryloxy and 3-arylthioazetidinecarboxamides |
| IN162808B (h) * | 1985-02-28 | 1988-07-09 | Robins Co Inc A H | |
| US5151418A (en) * | 1985-02-28 | 1992-09-29 | A. H. Robins Company, Incorporated | Method of treating muscular tension, muscle spasticity and anxiety with 3-aryloxy and 3-arylthioazetidinecarboxamides |
| US5183903A (en) * | 1991-11-26 | 1993-02-02 | A. H. Robins Company, Incorporated | Urea fusion process for the synthesis of 3-phenoxy-1-azetidinecarboxamides |
| JP4542264B2 (ja) * | 1998-01-23 | 2010-09-08 | バーナリス リサーチ リミテッド | Ｃｎｓ障害を処置するためのアゼチジンカルボキサミド誘導体 |
| US6403574B1 (en) | 1998-01-23 | 2002-06-11 | Vernalis Research Limited | Azetidinecarboxamide derivatives for treating CNS disorders |
| GB9917386D0 (en) * | 1999-07-23 | 1999-09-22 | Cerebrus Ltd | Chemical compounds-II |
| CN113754541B (zh) * | 2020-06-02 | 2025-01-03 | 深圳湾实验室 | 靶向eb病毒核抗原蛋白的小分子抑制剂、制备方法及其应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB872447A (en) * | 1958-12-23 | 1961-07-12 | Lepetit Spa | 1-carbamyl-3-substituted azetidines |
| US4226861A (en) * | 1978-04-18 | 1980-10-07 | A. H. Robins Company, Inc. | N-Lower-alkyl 3-phenoxy-1-azetidinecarboxamides |
-
1983
- 1983-05-13 IL IL68699A patent/IL68699A/xx unknown
- 1983-05-17 AU AU14597/83A patent/AU553528B2/en not_active Ceased
- 1983-06-13 ES ES523193A patent/ES8500225A1/es not_active Expired
- 1983-06-14 ZA ZA834371A patent/ZA834371B/xx unknown
- 1983-06-15 EG EG362/83A patent/EG16472A/xx active
- 1983-06-22 CA CA000430921A patent/CA1173841A/en not_active Expired
- 1983-07-04 IN IN830/CAL/83A patent/IN157045B/en unknown
- 1983-07-07 CS CS835172A patent/CS236796B2/cs unknown
- 1983-07-15 IE IE1651/83A patent/IE55769B1/en not_active IP Right Cessation
- 1983-07-26 YU YU1586/83A patent/YU44854B/xx unknown
- 1983-07-27 DE DE8383304348T patent/DE3367089D1/de not_active Expired
- 1983-07-27 EP EP83304348A patent/EP0102194B1/en not_active Expired
- 1983-08-01 PL PL1983243255A patent/PL140765B1/pl unknown
- 1983-08-02 JP JP58141815A patent/JPH0643388B2/ja not_active Expired - Lifetime
- 1983-08-11 GR GR72196A patent/GR79634B/el unknown
- 1983-08-17 KR KR1019830003825A patent/KR900001210B1/ko not_active Expired
- 1983-08-17 PH PH29408A patent/PH19595A/en unknown
- 1983-08-17 DK DK376183A patent/DK165741C/da not_active IP Right Cessation
- 1983-08-18 FI FI832956A patent/FI77225C/fi not_active IP Right Cessation
- 1983-08-18 PT PT77217A patent/PT77217B/pt not_active IP Right Cessation
- 1983-08-18 NO NO832971A patent/NO157976C/no unknown
- 1983-08-18 NZ NZ205317A patent/NZ205317A/en unknown
- 1983-08-18 HU HU832905A patent/HU190608B/hu not_active IP Right Cessation
-
1987
- 1987-06-18 HK HK474/87A patent/HK47487A/en not_active IP Right Cessation
-
1992
- 1992-06-26 MX MX9203639A patent/MX9203639A/es unknown
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