NO125535B - - Google Patents
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- Publication number
- NO125535B NO125535B NO207569A NO207569A NO125535B NO 125535 B NO125535 B NO 125535B NO 207569 A NO207569 A NO 207569A NO 207569 A NO207569 A NO 207569A NO 125535 B NO125535 B NO 125535B
- Authority
- NO
- Norway
- Prior art keywords
- thiadiazole
- hydroxypropoxy
- morpholino
- butylamino
- hydroxy
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 113
- -1 morpholino, N-methyl-piperazino Chemical group 0.000 claims description 111
- 239000000203 mixture Substances 0.000 claims description 80
- 238000002360 preparation method Methods 0.000 claims description 66
- 150000001875 compounds Chemical class 0.000 claims description 60
- 239000000460 chlorine Substances 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 36
- 150000001412 amines Chemical class 0.000 claims description 31
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 30
- 239000001294 propane Substances 0.000 claims description 25
- 229910052801 chlorine Inorganic materials 0.000 claims description 23
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 23
- 239000002585 base Substances 0.000 claims description 21
- 229910052783 alkali metal Inorganic materials 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 150000003461 sulfonyl halides Chemical class 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 150000002118 epoxides Chemical class 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
- 239000011707 mineral Substances 0.000 claims description 7
- 238000005932 reductive alkylation reaction Methods 0.000 claims description 7
- 230000002829 reductive effect Effects 0.000 claims description 7
- 239000012279 sodium borohydride Substances 0.000 claims description 7
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 7
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 6
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 150000004868 1,2,5-thiadiazoles Chemical class 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 241000223208 Curvularia Species 0.000 claims description 3
- 241000223211 Curvularia lunata Species 0.000 claims description 3
- 244000168141 Geotrichum candidum Species 0.000 claims description 3
- 235000017388 Geotrichum candidum Nutrition 0.000 claims description 3
- 241000187432 Streptomyces coelicolor Species 0.000 claims description 3
- 241000187389 Streptomyces lavendulae Species 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 238000011534 incubation Methods 0.000 claims description 3
- 241000589220 Acetobacter Species 0.000 claims description 2
- 241000194107 Bacillus megaterium Species 0.000 claims description 2
- 241000588919 Citrobacter freundii Species 0.000 claims description 2
- 241000193403 Clostridium Species 0.000 claims description 2
- 241000193167 Clostridium cochlearium Species 0.000 claims description 2
- 241000588724 Escherichia coli Species 0.000 claims description 2
- 241000588915 Klebsiella aerogenes Species 0.000 claims description 2
- 241000186673 Lactobacillus delbrueckii Species 0.000 claims description 2
- 241000192130 Leuconostoc mesenteroides Species 0.000 claims description 2
- 241001139337 Mycobacterium lacticola Species 0.000 claims description 2
- 241000203720 Pimelobacter simplex Species 0.000 claims description 2
- 241000531795 Salmonella enterica subsp. enterica serovar Paratyphi A Species 0.000 claims description 2
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 2
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 158
- 239000000047 product Substances 0.000 description 94
- 239000000243 solution Substances 0.000 description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 64
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 60
- 238000002844 melting Methods 0.000 description 54
- 230000008018 melting Effects 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 50
- 238000006243 chemical reaction Methods 0.000 description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- IMRVHHZSCBRFMT-UHFFFAOYSA-N 1-(tert-butylamino)-3-[(4-chloro-1,2,5-thiadiazol-3-yl)oxy]propan-2-ol Chemical compound CC(C)(C)NCC(O)COC1=NSN=C1Cl IMRVHHZSCBRFMT-UHFFFAOYSA-N 0.000 description 32
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 30
- 239000003921 oil Substances 0.000 description 26
- 235000019198 oils Nutrition 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 230000008569 process Effects 0.000 description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 239000012458 free base Substances 0.000 description 18
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 18
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 18
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- 238000004458 analytical method Methods 0.000 description 16
- 238000001914 filtration Methods 0.000 description 16
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- DWUZILHYAJBUBR-UHFFFAOYSA-N 4-morpholin-4-yl-1,2,5-thiadiazol-3-one Chemical compound OC1=NSN=C1N1CCOCC1 DWUZILHYAJBUBR-UHFFFAOYSA-N 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- 238000007792 addition Methods 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- BLJRIMJGRPQVNF-UHFFFAOYSA-N timolol Chemical compound CC(C)(C)NCC(O)COC1=NSN=C1N1CCOCC1 BLJRIMJGRPQVNF-UHFFFAOYSA-N 0.000 description 15
- WLRMANUAADYWEA-BTJKTKAUSA-N (z)-but-2-enedioic acid;1-(tert-butylamino)-3-[(4-morpholin-4-yl-1,2,5-thiadiazol-3-yl)oxy]propan-2-ol Chemical compound OC(=O)\C=C/C(O)=O.CC(C)(C)NCC(O)COC1=NSN=C1N1CCOCC1 WLRMANUAADYWEA-BTJKTKAUSA-N 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 235000019441 ethanol Nutrition 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 14
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- 239000011976 maleic acid Substances 0.000 description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 13
- 239000007858 starting material Substances 0.000 description 13
- FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000000376 reactant Substances 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 11
- 239000012259 ether extract Substances 0.000 description 11
- 238000001704 evaporation Methods 0.000 description 11
- 230000008020 evaporation Effects 0.000 description 11
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 10
- 150000001299 aldehydes Chemical class 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 238000003776 cleavage reaction Methods 0.000 description 10
- 238000002955 isolation Methods 0.000 description 10
- 229940073584 methylene chloride Drugs 0.000 description 10
- 230000007017 scission Effects 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 238000006722 reduction reaction Methods 0.000 description 9
- KQVWXSSZBACJMG-UHFFFAOYSA-N 1-(tert-butylamino)-3-[(4-chloro-1,2,5-thiadiazol-3-yl)oxy]propan-2-ol;hydrochloride Chemical compound Cl.CC(C)(C)NCC(O)COC1=NSN=C1Cl KQVWXSSZBACJMG-UHFFFAOYSA-N 0.000 description 8
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 8
- LAUCCQWGVCJGFT-UHFFFAOYSA-N 4-(4-chloro-1,2,5-thiadiazol-3-yl)morpholine Chemical compound ClC1=NSN=C1N1CCOCC1 LAUCCQWGVCJGFT-UHFFFAOYSA-N 0.000 description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 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 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 7
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 239000000908 ammonium hydroxide Substances 0.000 description 7
- 238000005984 hydrogenation reaction Methods 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 230000009467 reduction Effects 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
- 150000004867 thiadiazoles Chemical group 0.000 description 7
- BHBZGQBBRQJXCY-UHFFFAOYSA-N 4-chloro-1,2,5-thiadiazol-3-one Chemical compound OC1=NSN=C1Cl BHBZGQBBRQJXCY-UHFFFAOYSA-N 0.000 description 6
- RPPQQUKGLMBRDC-UHFFFAOYSA-N 4-ethyl-1,2,5-thiadiazol-3-one Chemical compound CCC1=NSN=C1O RPPQQUKGLMBRDC-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- MNQZXJOMYWMBOU-VKHMYHEASA-N D-glyceraldehyde Chemical compound OC[C@@H](O)C=O MNQZXJOMYWMBOU-VKHMYHEASA-N 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- SGPDZNJWEUIJNL-UHFFFAOYSA-N [3-(tert-butylamino)-2-oxopropyl] phenylmethanesulfonate Chemical compound C(C1=CC=CC=C1)S(=O)(=O)OCC(CNC(C)(C)C)=O SGPDZNJWEUIJNL-UHFFFAOYSA-N 0.000 description 6
- 239000002876 beta blocker Substances 0.000 description 6
- 229940030611 beta-adrenergic blocking agent Drugs 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical class [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical group C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 5
- WTUHODURKNXYTR-UHFFFAOYSA-N 4-ethoxy-1,2,5-thiadiazol-3-one Chemical compound CCOC1=NSN=C1O WTUHODURKNXYTR-UHFFFAOYSA-N 0.000 description 5
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 5
- 230000001580 bacterial effect Effects 0.000 description 5
- 229960000846 camphor Drugs 0.000 description 5
- 239000003638 chemical reducing agent Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 5
- APEJDIWDAXIRHL-UHFFFAOYSA-N 1-(tert-butylamino)-3-[(4-morpholin-4-yl-1,2,5-thiadiazol-3-yl)oxy]propan-2-ol;hydrochloride Chemical compound Cl.CC(C)(C)NCC(O)COC1=NSN=C1N1CCOCC1 APEJDIWDAXIRHL-UHFFFAOYSA-N 0.000 description 4
- RRDOTMYMDFQMSL-UHFFFAOYSA-N 1-(tert-butylamino)-3-[(4-morpholin-4-yl-1,2,5-thiadiazol-3-yl)oxy]propan-2-one Chemical compound CC(C)(C)NCC(=O)COC1=NSN=C1N1CCOCC1 RRDOTMYMDFQMSL-UHFFFAOYSA-N 0.000 description 4
- YVUMOIGTUXACII-UHFFFAOYSA-N 1-(tert-butylamino)-3-hydroxypropan-2-one Chemical compound C(C)(C)(C)NCC(CO)=O YVUMOIGTUXACII-UHFFFAOYSA-N 0.000 description 4
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- GLKNXXLWVDKKNI-UHFFFAOYSA-N 4-phenyl-1,2,5-thiadiazol-3-one Chemical compound OC1=NSN=C1C1=CC=CC=C1 GLKNXXLWVDKKNI-UHFFFAOYSA-N 0.000 description 4
- 241000203809 Actinomycetales Species 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000001640 fractional crystallisation Methods 0.000 description 4
- 230000002538 fungal effect Effects 0.000 description 4
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 235000005985 organic acids Nutrition 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 235000013849 propane Nutrition 0.000 description 4
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- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73133368A | 1968-05-22 | 1968-05-22 | |
| US81808669A | 1969-04-21 | 1969-04-21 | |
| US81847469A | 1969-04-21 | 1969-04-21 | |
| US81809069A | 1969-04-21 | 1969-04-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO125535B true NO125535B (da) | 1972-09-25 |
Family
ID=27505594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO207569A NO125535B (da) | 1968-05-22 | 1969-05-21 |
Country Status (3)
| Country | Link |
|---|---|
| DK (1) | DK135771B (da) |
| IL (2) | IL32239A (da) |
| NO (1) | NO125535B (da) |
-
1969
- 1969-05-19 IL IL32239A patent/IL32239A/en unknown
- 1969-05-21 DK DK274069A patent/DK135771B/da not_active IP Right Cessation
- 1969-05-21 NO NO207569A patent/NO125535B/no unknown
-
1973
- 1973-10-01 IL IL43351A patent/IL43351A0/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL32239A0 (en) | 1969-07-30 |
| IL43351A0 (en) | 1974-01-14 |
| IL32239A (en) | 1974-12-31 |
| DK135771C (da) | 1977-11-21 |
| DK135771B (da) | 1977-06-20 |
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