NO855210L - Fremgangsmaate ved fremstilling av n-substituerte aziridin-2-carboxylsyrederivater. - Google Patents
Fremgangsmaate ved fremstilling av n-substituerte aziridin-2-carboxylsyrederivater.Info
- Publication number
- NO855210L NO855210L NO855210A NO855210A NO855210L NO 855210 L NO855210 L NO 855210L NO 855210 A NO855210 A NO 855210A NO 855210 A NO855210 A NO 855210A NO 855210 L NO855210 L NO 855210L
- Authority
- NO
- Norway
- Prior art keywords
- general formula
- methyl
- carboxylic acid
- pyridine
- compounds
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- -1 N-SUBSTITUTED AZIRIDIN-2-CARBOXYLIC ACID Chemical class 0.000 title abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 48
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 8
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 8
- 150000001204 N-oxides Chemical class 0.000 claims description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 230000002519 immonomodulatory effect Effects 0.000 abstract description 4
- 230000003308 immunostimulating effect Effects 0.000 abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000012279 sodium borohydride Substances 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- SSNSWWCPJYINQR-UHFFFAOYSA-N 5-(aminomethyl)-6-ethoxypyridine-2-carboxylic acid Chemical compound CCOC1=NC(C(O)=O)=CC=C1CN SSNSWWCPJYINQR-UHFFFAOYSA-N 0.000 description 3
- SZLMBSZFIPPNLS-UHFFFAOYSA-N 5-[(2-cyanoaziridin-1-yl)methyl]-6-methoxypyridine-2-carboxylic acid Chemical compound COC1=NC(C(O)=O)=CC=C1CN1C(C#N)C1 SZLMBSZFIPPNLS-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000001541 aziridines Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- XRKQMIFKHDXFNQ-UHFFFAOYSA-N n-cyclohexyl-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)C1CCCCC1 XRKQMIFKHDXFNQ-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000006303 photolysis reaction Methods 0.000 description 3
- 230000015843 photosynthesis, light reaction Effects 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000012286 potassium permanganate Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000001149 thermolysis Methods 0.000 description 3
- ZLRDQJALIHIIBC-UHFFFAOYSA-N 1-[[6-(hydroxymethyl)-2-methoxypyridin-3-yl]methyl]aziridine-2-carbonitrile Chemical compound COC1=NC(CO)=CC=C1CN1C(C#N)C1 ZLRDQJALIHIIBC-UHFFFAOYSA-N 0.000 description 2
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 2
- CMPIGRYBIGUGTH-UHFFFAOYSA-N 2-bromoprop-2-enenitrile Chemical compound BrC(=C)C#N CMPIGRYBIGUGTH-UHFFFAOYSA-N 0.000 description 2
- IKFOKDPFANICQA-UHFFFAOYSA-N 5-(aminomethyl)-6-methoxypyridine-2-carboxylic acid Chemical compound COC1=NC(C(O)=O)=CC=C1CN IKFOKDPFANICQA-UHFFFAOYSA-N 0.000 description 2
- KEOYOLCFQXJOKL-UHFFFAOYSA-N 5-[(2-cyanoaziridin-1-yl)methyl]-6-ethoxypyridine-2-carboxylic acid Chemical compound CCOC1=NC(C(O)=O)=CC=C1CN1C(C#N)C1 KEOYOLCFQXJOKL-UHFFFAOYSA-N 0.000 description 2
- CDHWPCZSQRWYMP-UHFFFAOYSA-N 5-cyano-6-methoxypyridine-2-carboxylic acid Chemical compound COC1=NC(C(O)=O)=CC=C1C#N CDHWPCZSQRWYMP-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical class [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WBGBOXYJYPVLQJ-UHFFFAOYSA-N aziridine-2-carboxylic acid Chemical class OC(=O)C1CN1 WBGBOXYJYPVLQJ-UHFFFAOYSA-N 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 239000002955 immunomodulating agent Substances 0.000 description 2
- 229940121354 immunomodulator Drugs 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
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- 230000035484 reaction time Effects 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- GMGNWYYUNSETFU-UHFFFAOYSA-N 1-[(2-methoxy-6-methoxycarbonylpyridin-3-yl)methyl]aziridine-2-carboxylic acid Chemical compound COC1=NC(C(=O)OC)=CC=C1CN1C(C(O)=O)C1 GMGNWYYUNSETFU-UHFFFAOYSA-N 0.000 description 1
- KOYMTVWMCXDJNV-UHFFFAOYSA-N 1-[(2-methoxy-6-methylpyridin-3-yl)methyl]aziridine-2-carbonitrile Chemical compound COC1=NC(C)=CC=C1CN1C(C#N)C1 KOYMTVWMCXDJNV-UHFFFAOYSA-N 0.000 description 1
- MTDQMWULDLUDQI-UHFFFAOYSA-N 1-[(6-carbamoyl-2-methoxypyridin-3-yl)methyl]aziridine-2-carboxylic acid Chemical compound COC1=NC(C(N)=O)=CC=C1CN1C(C(O)=O)C1 MTDQMWULDLUDQI-UHFFFAOYSA-N 0.000 description 1
- AKAYUHFZBCEKBJ-UHFFFAOYSA-N 1-[(6-carbamoyl-2-oxo-1h-pyridin-3-yl)methyl]aziridine-2-carboxylic acid Chemical compound OC1=NC(C(=O)N)=CC=C1CN1C(C(O)=O)C1 AKAYUHFZBCEKBJ-UHFFFAOYSA-N 0.000 description 1
- DEHCMZZWKIWBAP-UHFFFAOYSA-N 1-[(6-methoxycarbonyl-2-oxo-1h-pyridin-3-yl)methyl]aziridine-2-carboxylic acid Chemical compound OC1=NC(C(=O)OC)=CC=C1CN1C(C(O)=O)C1 DEHCMZZWKIWBAP-UHFFFAOYSA-N 0.000 description 1
- WYUPLQUAWSBZAW-UHFFFAOYSA-N 1-[[6-(hydroxymethyl)-2-methoxypyridin-3-yl]methyl]aziridine-2-carboxamide Chemical compound COC1=NC(CO)=CC=C1CN1C(C(N)=O)C1 WYUPLQUAWSBZAW-UHFFFAOYSA-N 0.000 description 1
- RXWLELRLAZHSMO-UHFFFAOYSA-N 1-[[6-(hydroxymethyl)-2-methoxypyridin-3-yl]methyl]aziridine-2-carboxylic acid Chemical compound COC1=NC(CO)=CC=C1CN1C(C(O)=O)C1 RXWLELRLAZHSMO-UHFFFAOYSA-N 0.000 description 1
- VLVSTSMRZKROIN-UHFFFAOYSA-N 1-[[6-(hydroxymethyl)-2-oxo-1h-pyridin-3-yl]methyl]aziridine-2-carbonitrile Chemical compound OC1=NC(CO)=CC=C1CN1C(C#N)C1 VLVSTSMRZKROIN-UHFFFAOYSA-N 0.000 description 1
- KXJPOAMJDBDVDS-UHFFFAOYSA-N 1-[[6-(hydroxymethyl)-2-oxo-1h-pyridin-3-yl]methyl]aziridine-2-carboxamide Chemical compound NC(=O)C1CN1CC1=CC=C(CO)N=C1O KXJPOAMJDBDVDS-UHFFFAOYSA-N 0.000 description 1
- VBYYPIBQUSRYFM-UHFFFAOYSA-N 1-[[6-(hydroxymethyl)-2-oxo-1h-pyridin-3-yl]methyl]aziridine-2-carboxylic acid Chemical compound OC1=NC(CO)=CC=C1CN1C(C(O)=O)C1 VBYYPIBQUSRYFM-UHFFFAOYSA-N 0.000 description 1
- FQUCJDIGQIESAR-UHFFFAOYSA-N 2-chloro-6-methyl-1h-pyridine-2-carbonitrile Chemical compound CC1=CC=CC(Cl)(C#N)N1 FQUCJDIGQIESAR-UHFFFAOYSA-N 0.000 description 1
- DEIPEASEZNGTSV-UHFFFAOYSA-N 2-ethoxy-6-methylpyridine-3-carbonitrile Chemical compound CCOC1=NC(C)=CC=C1C#N DEIPEASEZNGTSV-UHFFFAOYSA-N 0.000 description 1
- IDUHMLQSIWHQKZ-UHFFFAOYSA-N 2-methoxy-6-methylpyridine-3-carbonitrile Chemical compound COC1=NC(C)=CC=C1C#N IDUHMLQSIWHQKZ-UHFFFAOYSA-N 0.000 description 1
- OADHHNNSFWEIPS-UHFFFAOYSA-N 5-[(2-carbamoylaziridin-1-yl)methyl]-6-methoxypyridine-2-carboxylic acid Chemical compound COC1=NC(C(O)=O)=CC=C1CN1C(C(N)=O)C1 OADHHNNSFWEIPS-UHFFFAOYSA-N 0.000 description 1
- XKQQBEDIPGVROX-UHFFFAOYSA-N 5-[(2-carbamoylaziridin-1-yl)methyl]-6-oxo-1h-pyridine-2-carboxylic acid Chemical compound NC(=O)C1CN1CC1=CC=C(C(O)=O)N=C1O XKQQBEDIPGVROX-UHFFFAOYSA-N 0.000 description 1
- NZSUMTBRXAPSDS-UHFFFAOYSA-N 5-[(2-carboxyaziridin-1-yl)methyl]-6-methoxypyridine-2-carboxylic acid Chemical compound COC1=NC(C(O)=O)=CC=C1CN1C(C(O)=O)C1 NZSUMTBRXAPSDS-UHFFFAOYSA-N 0.000 description 1
- PZQIGIQIJRUIIZ-UHFFFAOYSA-N 5-[(2-carboxyaziridin-1-yl)methyl]-6-oxo-1h-pyridine-2-carboxylic acid Chemical compound OC(=O)C1CN1CC1=CC=C(C(O)=O)N=C1O PZQIGIQIJRUIIZ-UHFFFAOYSA-N 0.000 description 1
- LEKFKWUQAHSNTO-UHFFFAOYSA-N 5-[(2-cyanoaziridin-1-yl)methyl]-6-oxo-1h-pyridine-2-carboxylic acid Chemical compound OC1=NC(C(=O)O)=CC=C1CN1C(C#N)C1 LEKFKWUQAHSNTO-UHFFFAOYSA-N 0.000 description 1
- YRTKVSSZIXZCPA-UHFFFAOYSA-N 5-[(2-ethoxycarbonylaziridin-1-yl)methyl]-6-methoxypyridine-2-carboxylic acid Chemical compound CCOC(=O)C1CN1CC1=CC=C(C(O)=O)N=C1OC YRTKVSSZIXZCPA-UHFFFAOYSA-N 0.000 description 1
- FSSMGYGLKUFPTF-UHFFFAOYSA-N 5-[(2-ethoxycarbonylaziridin-1-yl)methyl]-6-oxo-1h-pyridine-2-carboxylic acid Chemical compound CCOC(=O)C1CN1CC1=CC=C(C(O)=O)N=C1O FSSMGYGLKUFPTF-UHFFFAOYSA-N 0.000 description 1
- FBKRIVQNAKSKBL-UHFFFAOYSA-N 5-cyano-6-ethoxypyridine-2-carboxylic acid Chemical compound CCOC1=NC(C(O)=O)=CC=C1C#N FBKRIVQNAKSKBL-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
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- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- 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 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
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- 150000001414 amino alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
- 229910000085 borane Inorganic materials 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
- 239000002775 capsule Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- KQPGCIIYXNRIMU-UHFFFAOYSA-N ethyl 1-[(6-carbamoyl-2-methoxypyridin-3-yl)methyl]aziridine-2-carboxylate Chemical compound CCOC(=O)C1CN1CC1=CC=C(C(N)=O)N=C1OC KQPGCIIYXNRIMU-UHFFFAOYSA-N 0.000 description 1
- SJYBWWLQHJIGQM-UHFFFAOYSA-N ethyl 1-[[6-(hydroxymethyl)-2-oxo-1h-pyridin-3-yl]methyl]aziridine-2-carboxylate Chemical compound CCOC(=O)C1CN1CC1=CC=C(CO)N=C1O SJYBWWLQHJIGQM-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 1
- 230000035874 hyperreactivity Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000016784 immunoglobulin production Effects 0.000 description 1
- 230000004957 immunoregulator effect Effects 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- KSXQRYUHBMAREL-UHFFFAOYSA-N methyl 3-methoxypyridine-2-carboxylate Chemical compound COC(=O)C1=NC=CC=C1OC KSXQRYUHBMAREL-UHFFFAOYSA-N 0.000 description 1
- PLAZZEMQCLWSSA-UHFFFAOYSA-N methyl 5-(aminomethyl)-6-methoxypyridine-2-carboxylate Chemical compound COC(=O)C1=CC=C(CN)C(OC)=N1 PLAZZEMQCLWSSA-UHFFFAOYSA-N 0.000 description 1
- VYCBCVDKEUXBCJ-UHFFFAOYSA-N methyl 5-[(2-carbamoylaziridin-1-yl)methyl]-6-oxo-1h-pyridine-2-carboxylate Chemical compound OC1=NC(C(=O)OC)=CC=C1CN1C(C(N)=O)C1 VYCBCVDKEUXBCJ-UHFFFAOYSA-N 0.000 description 1
- QIDXRLXSKMXLJO-UHFFFAOYSA-N methyl 5-[(2-cyanoaziridin-1-yl)methyl]-6-methoxypyridine-2-carboxylate Chemical compound COC1=NC(C(=O)OC)=CC=C1CN1C(C#N)C1 QIDXRLXSKMXLJO-UHFFFAOYSA-N 0.000 description 1
- LCPRMKWASWNGSG-UHFFFAOYSA-N methyl 5-[(2-cyanoaziridin-1-yl)methyl]-6-oxo-1h-pyridine-2-carboxylate Chemical compound OC1=NC(C(=O)OC)=CC=C1CN1C(C#N)C1 LCPRMKWASWNGSG-UHFFFAOYSA-N 0.000 description 1
- VSGKPWGNFVPZFP-UHFFFAOYSA-N methyl 5-[(2-ethoxycarbonylaziridin-1-yl)methyl]-6-oxo-1H-pyridine-2-carboxylate Chemical compound CCOC(=O)C1CN1CC1=CC=C(C(=O)OC)NC1=O VSGKPWGNFVPZFP-UHFFFAOYSA-N 0.000 description 1
- AQGAHULDJSYQTR-UHFFFAOYSA-N methyl 5-cyano-6-methoxypyridine-2-carboxylate Chemical compound COC(=O)C1=CC=C(C#N)C(OC)=N1 AQGAHULDJSYQTR-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- MMKQSIQNDMIVIN-UHFFFAOYSA-N oxido-(oxido(dioxo)chromio)oxy-dioxochromium;tetrabutylazanium Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC MMKQSIQNDMIVIN-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
- 206010043778 thyroiditis Diseases 0.000 description 1
- 125000004954 trialkylamino group Chemical group 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
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Pyridine Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843446713 DE3446713A1 (de) | 1984-12-21 | 1984-12-21 | N-substituierte aziridin-2-carbonsaeurederivate, verfahren zu deren herstellung sowie diese substanzen enthaltende arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO855210L true NO855210L (no) | 1986-06-23 |
Family
ID=6253432
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO855210A NO855210L (no) | 1984-12-21 | 1985-12-20 | Fremgangsmaate ved fremstilling av n-substituerte aziridin-2-carboxylsyrederivater. |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4826858A (fr) |
| EP (1) | EP0186049B1 (fr) |
| JP (1) | JPS61152678A (fr) |
| CN (1) | CN85108698B (fr) |
| AT (1) | ATE54315T1 (fr) |
| AU (2) | AU578335B2 (fr) |
| CS (1) | CS256395B2 (fr) |
| DD (1) | DD246299A5 (fr) |
| DE (2) | DE3446713A1 (fr) |
| DK (1) | DK591685A (fr) |
| ES (1) | ES8800198A1 (fr) |
| FI (1) | FI854985A (fr) |
| GR (1) | GR853057B (fr) |
| HU (1) | HU194869B (fr) |
| IL (1) | IL77357A (fr) |
| NO (1) | NO855210L (fr) |
| NZ (1) | NZ214596A (fr) |
| PH (1) | PH23039A (fr) |
| PL (1) | PL148867B1 (fr) |
| PT (1) | PT81702B (fr) |
| SU (1) | SU1431676A3 (fr) |
| YU (1) | YU199985A (fr) |
| ZA (1) | ZA859592B (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100738229B1 (ko) * | 2001-12-31 | 2007-07-12 | 한국화학연구원 | 신규한 피롤리디닐피리딘 유도체 |
| MXPA06006428A (es) * | 2003-12-12 | 2006-08-23 | Syngenta Participations Ag | Nuevos herbicidas. |
| WO2009153179A1 (fr) | 2008-06-16 | 2009-12-23 | F. Hoffmann-La Roche Ag | Dérivés de pyrrolidine servant d’antagonistes des récepteurs nk2 |
| CN105272896A (zh) * | 2015-10-19 | 2016-01-27 | 山东国润生物医药有限公司 | (（2s）-2-氮丙啶基)二苯基甲醇的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2833986A1 (de) * | 1978-08-03 | 1980-02-21 | Boehringer Mannheim Gmbh | Immunstimulierende n-substituierte aziridin-2-carbonsaeurederivate, verfahren zu ihrer herstellung sowie arzneimittel, die diese substanzen enthalten |
| DE3211254A1 (de) * | 1982-03-26 | 1983-09-29 | Boehringer Mannheim Gmbh, 6800 Mannheim | Verfahren zum nachweis des vorliegens einer allergie und zum spezifischen nachweis des fuer die allergie verantwortlichen allergens |
-
1984
- 1984-12-21 DE DE19843446713 patent/DE3446713A1/de not_active Withdrawn
-
1985
- 1985-12-11 DE DE8585115785T patent/DE3578563D1/de not_active Expired - Lifetime
- 1985-12-11 EP EP85115785A patent/EP0186049B1/fr not_active Expired - Lifetime
- 1985-12-11 AT AT85115785T patent/ATE54315T1/de not_active IP Right Cessation
- 1985-12-16 IL IL77357A patent/IL77357A/xx unknown
- 1985-12-16 DD DD85284394A patent/DD246299A5/de unknown
- 1985-12-16 FI FI854985A patent/FI854985A/fi not_active Application Discontinuation
- 1985-12-16 PH PH33180A patent/PH23039A/en unknown
- 1985-12-16 AU AU51265/85A patent/AU578335B2/en not_active Ceased
- 1985-12-17 ZA ZA859592A patent/ZA859592B/xx unknown
- 1985-12-17 JP JP60282177A patent/JPS61152678A/ja active Pending
- 1985-12-17 NZ NZ214596A patent/NZ214596A/xx unknown
- 1985-12-18 GR GR853057A patent/GR853057B/el unknown
- 1985-12-18 PT PT81702A patent/PT81702B/pt unknown
- 1985-12-18 DK DK591685A patent/DK591685A/da not_active Application Discontinuation
- 1985-12-19 PL PL1985256941A patent/PL148867B1/pl unknown
- 1985-12-19 YU YU01999/85A patent/YU199985A/xx unknown
- 1985-12-19 CS CS859547A patent/CS256395B2/cs unknown
- 1985-12-20 NO NO855210A patent/NO855210L/no unknown
- 1985-12-20 SU SU853991691A patent/SU1431676A3/ru active
- 1985-12-20 ES ES550285A patent/ES8800198A1/es not_active Expired
- 1985-12-20 HU HU854938A patent/HU194869B/hu unknown
- 1985-12-21 CN CN85108698A patent/CN85108698B/zh not_active Expired
-
1987
- 1987-11-25 US US07/125,353 patent/US4826858A/en not_active Expired - Fee Related
-
1990
- 1990-02-01 AU AU49015/90A patent/AU625355B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| DE3578563D1 (de) | 1990-08-09 |
| FI854985A (fi) | 1986-06-22 |
| DE3446713A1 (de) | 1986-06-26 |
| ZA859592B (en) | 1986-09-24 |
| AU5126585A (en) | 1986-06-26 |
| PL148867B1 (en) | 1989-12-30 |
| ES550285A0 (es) | 1987-11-01 |
| US4826858A (en) | 1989-05-02 |
| IL77357A (en) | 1989-08-15 |
| NZ214596A (en) | 1988-10-28 |
| CN85108698B (zh) | 1988-09-07 |
| AU625355B2 (en) | 1992-07-09 |
| PH23039A (en) | 1989-03-10 |
| GR853057B (fr) | 1986-04-15 |
| DK591685A (da) | 1986-06-22 |
| AU578335B2 (en) | 1988-10-20 |
| YU199985A (en) | 1987-12-31 |
| CS256395B2 (en) | 1988-04-15 |
| EP0186049A1 (fr) | 1986-07-02 |
| PT81702B (de) | 1987-08-10 |
| HUT40107A (en) | 1986-11-28 |
| HU194869B (en) | 1988-03-28 |
| EP0186049B1 (fr) | 1990-07-04 |
| AU4901590A (en) | 1990-08-02 |
| ES8800198A1 (es) | 1987-11-01 |
| PL256941A1 (en) | 1986-10-07 |
| FI854985A0 (fi) | 1985-12-16 |
| CS954785A2 (en) | 1987-08-13 |
| CN85108698A (zh) | 1986-07-23 |
| DK591685D0 (da) | 1985-12-18 |
| PT81702A (de) | 1986-01-02 |
| JPS61152678A (ja) | 1986-07-11 |
| ATE54315T1 (de) | 1990-07-15 |
| DD246299A5 (de) | 1987-06-03 |
| SU1431676A3 (ru) | 1988-10-15 |
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